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843 things you should know to secure top 100 Rank in IIT -JEE

Physical & General Chemistry

General Chemistry
1 Apply the law of the conservation of mass. 2 Compare and contrast the three common states of matter: solid, liquid, and gas.

Done

Describe the classifications of matter: elements, compounds, and mixtures

3 (heterogeneous and homogeneous). 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44

Understand the difference between chemical changes (chemical reactions) and physical changes. Distinguish between chemical properties and physical properties. Become familiar with the SI (metric) system of units, including the SI prefixes. Convert from one temperature scale to another. Calculate the density of a substance. Use density to relate mass and volume. Apply dimensional analysis to solving numerical problems. Convert from one metric unit to another metric unit. Convert from one metric volume to another metric volume. Convert from any unit to another unit. Atoms, Molecules, and Ions Describe Thomsons experiment in which he discovered the electron. Describe Rutherfords experiment that led to the nuclear model of the atom. Write the nuclide symbol for a given nuclide. Define and provide examples ofisotopes of an element. Write the nuclide symbol of an element. Determine the atomic mass of an element from the isotopic masses and fractional abundances. Determine when thechemical formula of a compound represents amolecule. Determine whether a chemical formula is also amolecular formula. Defineion, cation, andanion. Classify compounds asionic ormolecular. Define and provide examples for the termformula unit. Specify the charge on all substances, ionic and molecular. Write an ionic formula, given the ions. Learn the rules for predicting the charges ofmonatomic ions in ionic compounds. Apply the rules for naming monatomic ions. Learn the names and charges of commonpolyatomic ions. Name an ionic compound from its formula. Write the formula of an ionic compound from its name. Determine the order of elements in abinary (molecular) compound. Learn the rules for naming binary molecular compounds, including the Greek prefixes. Name a binary compound from its formula. Write the formula of a binary compound from its name. Name a binary molecular compound from its molecular model. Recognize molecular compounds that are acids. Determine whether an acid is anoxoacid. Learn the approach for naming binary acids and oxoacids. Write the name and formula of an anion from the acid. Recognize compounds that arehydrates. Learn the rules for naming hydrates. Name a hydrate from its formula. Write the formula of a hydrate from its name.

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Write chemical equations using appropriate phase labels, symbols of reaction
45 conditions, and the presence of a catalyst. 46 Determine if a chemical reaction is balanced. 47 Master the techniques for balancing chemical equations. 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71

Calculations with Chemical Formulas and Equations Calculate the formula mass from a formula. Calculate the formula mass from molecular models. Define the quantity called themole. LearnAvogadros number. Understand how themolar mass is related to the formula mass of a substance. Calculate the mass of atoms and molecules. Perform calculations using the mole. Convert from moles of substance to grams of substance. Convert from grams of substance to moles of substance. Calculate the number of molecules in a given mass of substance. Define mass percentage. Calculate the percentage composition of the elements in a compound. Calculate the mass of an element in a given mass of compound. Describe how C, H, and O combustion analysis is performed. Calculate the percentage of C, H, and O from combustion data. Define empirical formula. Determine the empirical formula of a binary compound from the masses of its elements. Determine the empirical formula from the percentage composition. Understand the relationship between the molecular mass of a substance and its empirical formula mass. Determine the molecular formula from the percentage composition and molecular mass. Relate the coefficients in a balanced chemical equation to the number of molecules or moles (molar interpretation ). Use the coefficients in a chemical reaction to perform calculations. Relate the quantities of reactant to the quantity of product. Relate the quantities of two reactants or two products. Understand how alimiting reactant orlimiting reagent determines the moles of product formed during a chemical reaction and how muchexcess reactant remains. Calculate with a limiting reactant involving moles. Calculate with a limiting reactant involving masses. Define and calculate thetheoretical yield of chemical reactions. Determine thepercentage yield of a chemical reaction. From the molecular equation of both strong electrolytes and weak electrolytes, determine thecomplete ionic equation. From the complete ionic equation, write thenet ionic equation. Write net ionic equations. Recognizeprecipitation (exchange ) reactions. Write molecular, complete ionic, and net ionic equations for precipitation reactions.

72 73 74 75 76 77 78 79 80

81 82 Decide whether a precipitation reaction will occur. 83 Determine the product of a precipitation reaction. 84 85 86 87 88

Understand how anacidbase indicator is used to determine whether a solution is acidic or basic. DefineArrhenius acid andArrhenius base. Write the chemical equation of an Arrhenius base in aqueous solution. DefineBrnsted Lowry acid andBrnsted Lowry base. Write the chemical equation of a BrnstedLowry base in aqueous solution.

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89 90 Learn the commonstrong acids andstrong bases. 91 Distinguish between a strong acid and aweak acid and the solutions they form. 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139

Write the chemical equation of an acid in aqueous solution using ahydronium ion.

Distinguish between a strong base and aweak base and the solutions they form. Classify acids and bases as strong or weak. Recognizeneutralization reactions. Write an equation for a neutralization reaction. Write the reactions for apolyprotic acid in aqueous solution. Recognize acidbase reactions that lead to gas formation. Write an equation for a reaction with gas formation. Defineoxidation reduction reaction. Learn the oxidation-number rules. Assign oxidation numbers. Write thehalf-reactions of an oxidationreduction reaction. Determine the species undergoingoxidation andreduction. Recognizecombination reactions, decomposition reactions, displacement reactions, andcombustion reactions. Use the activity series to predict when displacement reactions will occur. Balance simple oxidationreduction reactions by the half-reaction method. Define molarity or molar concentration of a solution. Calculate the molarity from mass and volume. Use molarity as a conversion factor. Describe what happens to the concentration of a solution when it is diluted. Perform calculations associated with dilution. Diluting a solution. Determine the amount of a species bygravimetric analysis. Calculate the volume of reactant solution needed to perform a reaction. Understand how to perform atitration . Calculate the quantity of substance in a titrated solution. The Gaseous State Definepressure and its units. Convert units of pressure. ExpressBoyles law in words and as an equation. Use Boyles law. ExpressCharless law in words and as an equation. Use Charless law. Express thecombined gas law as an equation. Use the combined gas law. StateAvogadros law. Definestandard temperature and pressure (STP ). State what makes a gas anideal gas. Learn theideal gas law equation. Derive the empirical gas laws from the ideal gas law. Use the ideal gas law. Calculate gas density. Determine the molecular mass of a vapor. Use an equation to calculate gas density. Solving stoichiometry problems involving gas volumes. Learn the equation for Daltons law of partial pressures. Define the mole fraction of a gas. Calculate the partial pressure and mole fractions of a gas in a mixture. Describe how gases are collected over water and how to determine the vapor pressure of water. Calculate the amount of gas collected over water.

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140 List the five postulates of thekinetic theory. 141 Provide a qualitative description of the gas laws based on the kinetic theory.

Describe how theroot-mean-square (rms) molecular speed of gas molecules varies with
142 temperature. 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190

Describe the molecular-speed distribution of gas molecules at different temperatures. Calculate the rms speed of gas molecules. Defineeffusion anddiffusion. Describe how individual gas molecules move undergoing diffusion. Calculate the ratio of effusion rates of gases. Explain how and why areal gas is different from an ideal gas. Use the van der Waals equation. Quantum Theory of the Atom Define thewavelength andfrequency of a wave. Relate the wavelength, frequency, and speed of light. Describe the different regions of the electromagnetic spectrum. State Plancks quantization of vibrational energy. DefinePlancks constant andphoton. Describe the photoelectric effect. Calculate the energy of a photon from its frequency or wavelength. State the postulates of Bohrs theory of the hydrogen atom. Relate the energy of a photon to the associated energy levels of an atom. Determine the wavelength or frequency of a hydrogen atom transition. Describe the difference betweenemission andabsorption of light by an atom. State the de Broglie relation. Calculate the wavelength of a moving particle. Definequantum mechanics. State Heisenbergs uncertainty principle. Relate the wave function for an electron to the probability of finding it at a location in space. Define atomic orbital. Define each of the quantum numbers for an atomic orbital. State the rules for the allowed values for each quantum number. Apply the rules for quantum numbers. Describe the shapes of s, p, and d orbitals. Electron Configurations and Periodicity Define electron configuration and orbital diagram. State the Pauli exclusion principle. Apply the Pauli exclusion principle. Define building-up principle. Define noble-gas core, pseudo-noble-gas core, and valence electron. Define main-group element and (d-block and f-block) transition element. Determine the configuration of an atom using the building-up principle. Determine the configuration of an atom using the period and group numbers. State Hunds rule. Apply Hunds rule. Defineparamagnetic substance anddiamagnetic substance. Describe how Mendeleev predicted the properties of undiscovered elements. State the periodic law. State the general periodic trends in size of atomic radii. Defineeffective nuclear charge. Determine relative atomic sizes from periodic trends. State the general periodic trends in ionization energy. Definefirst ionization energy. Determine relative ionization energies from periodic trends. Defineelectron affinity.

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191 State the broad general trend in electron affinity across any period. 192 Define basic oxide, acidic oxide, and amphoteric oxide.

State the main group corresponding to an alkali metal, an alkaline earth metal, a
193 chalcogen, a halogen, and a noble gas.

Describe the change in metallic/nonmetallic character (or reactivities) in going through

194 any main group of elements. 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237

Ionic and Covalent Bonding Define ionic bond. Explain the Lewis electron-dot symbol of an atom. Use Lewis symbols to represent ionic bond formation. Describe the energetics of ionic bonding. Define lattice energy. Describe the BornHaber cycle to obtain a lattice energy from thermodynamic data.

Describe some general properties of ionic substances. State the three categories of monatomic ions of the main-group elements. Write the electron configuration and Lewis symbol for a main-group ion. Note the polyatomic ions given earlier in Table 2.5. Note the formation of 2+ and 3+ transition-metal ions. Write electron configurations of transition-metal ions. Define ionic radius. Define isoelectronic ions. Use periodic trends to obtain relative ionic radii. Describe the formation of a covalent bond between two atoms. DefineLewis electron-dot formula. Definebonding pair andlone (nonbonding) pair of electrons. Definecoordinate covalent bond. State the octet rule. Definesingle bond, double bond, andtriple bond. Define polar covalent bond. Define electronegativity. State the general periodic trends in the electronegativity. Use electronegativity to obtain relative bond polarity. Write Lewis formulas with single bonds only. Write Lewis formulas having multiple bonds. Write Lewis formulas for ionic species. Define delocalized bonding. Define resonance description. Write resonance formulas. Write Lewis formulas (exceptions to the octet rule). Note exceptions to the octet rule in Group IIA and Group IIIA elements. Define formal charge. State the rules for obtaining formal charge. State two rules useful in writing Lewis formulas. Use formal charges to determine the best Lewis formula. Define bond length (bond distance). Define covalent radii. Define bond order. Explain how bond order and bond length are related. Define bond energy. Estimate H from bond energies. Molecular Geometry and Chemical Bonding Theory The Valence-Shell Electron-Pair Repulsion (VSEPR) Model 238 Define molecular geometry. 239 Define valence-shell electron-pair repulsion model.

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Note the difference between the arrangement of electron pairs about a central atom
240 and molecular geometry. 241 Note the four steps in the prediction of geometry by the VSEPR model. 242 Predict the molecular geometry (two, three, or four electron pairs).

Note that a lone pair tends to require more space than a corresponding bonding pair and that a multiple bond requires more space than a single bond. Predict the molecular geometry (five or six electron pairs). Define dipole moment. Explain the relationship between dipole moment and molecular geometry. Note that the polarity of a molecule can affect certain properties, such as a boiling 247 point. Valence Bond Theory 248 Define valence bond theory.
243 244 245 246 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266

State the two conditions needed for bond formation, according to valence bond theory. Define hybrid orbitals. State the five steps in describing bonding, following the valence bond theory. Apply valence bond theory (two, three, or four electron pairs). Apply valence bond theory (five or six electron pairs). Define (sigma )bond. Define (pi )bond. Apply valence bond theory (multiple bonding). Explain geometric, orcistrans, isomers in terms of the p-bond description of a double bond. Define molecular orbital theory. Define bonding orbitals and antibonding orbitals. Define bond order. State the two factors that determine the strength of interaction between two atomic orbitals. Describe the electron configurations of H 2, He2, Li2, and Be2. Define homonuclear diatomic molecules and heteronuclear diatomic molecules. Describe molecular orbital configurations (homonuclear diatomic molecules). Describe molecular orbital configurations (heteronuclear diatomic molecules). Describe the delocalized bonding in molecules such as O 3. States of Matter; Liquids and Solids Compare a gas, a liquid, and a solid using a kineticmolecular theory description.

267 268 Define change of state (phase transition). 269 Define melting, freezing, vaporization, sublimation, and condensation. 270 Define vapor pressure. 271 272 273 274 275 276

Describe the process of reaching a dynamic equilibrium that involves the vaporization of a liquid and condensation of its vapor. Define boiling point. Describe the process of boiling. Define freezing point and melting point. Define heat (enthalpy) of fusion and heat (enthalpy) of vaporization. Calculate the heat required for a phase change of a given mass of substance. Describe the general dependence of the vapor pressure (lnP ) on the temperature (T ).

277 278 Calculate the vapor pressure at a given temperature. 279 Calculate the heat of vaporization from vapor pressure. 280 Define phase diagram. 281 solid) in a phase diagram. 282 Define triple point. 283 Define critical temperature and critical pressure.

Describe the melting-point curve and the vapor-pressure curves (for the liquid and the

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284 285 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 335

Relate the conditions for the liquefaction of a gas to its critical temperature. Define intermolecular forces. Define dipoledipole force. Describe the alignment of polar molecules in a substance. Define London (dispersion) forces. Note that London forces tend to increase with molecular mass. Relate the properties of liquids to the intermolecular forces involved. Define hydrogen bonding. Identify the intermolecular forces in a substance. Determine relative vapor pressures on the basis of intermolecular attractions. Define molecular solid, metallic solid, ionic solid, and covalent network solid. Identify types of solids. Relate the melting point of a solid to its structure. Determine relative melting points based on types of solids. Relate the hardness and electrical conductivity of a solid to its structure. Define crystalline solid and amorphous solid. Define crystal lattice and unit cell of a crystal lattice. Define simple cubic unit cell, body-centered cubic unit cell, and face-centered cubic unit cell. Determine the number of atoms in a unit cell. Describe the two kinds of crystal defects. Define hexagonal close-packed structure and cubic close-packed structure. Define coordination number. Note the common structures (face-centered cubic and body-centered cubic) of metallic solids. Describe the three types of cubic structures of ionic solids. Describe the covalent network structure of diamond and graphite. Calculate atomic mass from unit-cell dimension and density. Calculate unit-cell dimension from unit-cell type and density. Solutions and Surface Chemistry Define solute and solvent. Define miscible fluid. Provide examples of gaseous solutions, liquid solutions, and solid solutions. List the conditions that must be present to have asaturated solution, to have anunsaturated solution, and to have asupersaturated solution. Describe the factors that make one substance soluble in another. Determine when amolecular solution will form when substances are mixed. Learn what conditions must be met in order to create anionic solution. State the general trends of the solubility of gases and solids with temperature. Explain how the solubility of a gas changes with temperature. Apply Henrys law. Define colligative property. Define molarity. Define mass percentage of solute. Calculate with mass percentage of solute. Define molality. Calculate the molality of solute. Define mole fraction. Calculate the mole fraction of components. Convert molality to mole fractions. Convert mole fractions to molality. Convert molality to molarity. Convert molarity to molality. Explain vapor-pressure lowering of a solvent. State Raoults law. Calculate vapor-pressure lowering.

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336 337 338 339 340 341 342 343 344 345 346 347 348 349 350 351 352 353 354 355 356

Describe an ideal solution. Define boiling-point elevation and freezing-point depression. Calculate boiling-point elevation and freezing-point depression. Calculate the molecular mass of a solute from molality. Calculate the molecular mass from freezing-point depression. Describe a system whereosmosis will take place. Calculate osmotic pressure. Determine the colligative properties of ionic solutions. Define colloid. Explain the Tyndall effect. Give examples of hydrophilic colloids and hydrophobic colloids. Describe coagulation. Explain how micelles can form an association colloid. Rates of Reaction Define reaction rate. Explain instantaneous rate and average rate of a reaction. Explain how the different ways of expressing reaction rates are related. Calculate average reaction rate. Describe how reaction rates may be experimentally determined. Define and provide examples of arate law ,rate constant, andreaction order. Determine the order of reaction from the rate law. Determine the rate law from initial rates. Learn the integrated rate laws for first-order, second-order, and zero-order reactions.

357 358 Use an integrated rate law. 359 Define half-life of a reaction.

360 361 Relate the half-life of a reaction to the rate constant. 362 Plot kinetic data to determine the order of a reaction. 363 State the postulates ofcollision theory. 364 Explainactivation energy (E a ).

Learn the half-life equations for first-order, second-order, and zero-order reactions.

Describe how temperature, activation energy, and molecular orientation influence

365 reaction rates. 366 State thetransition-state theory. 367 Defineactivated complex. 368 369 370 371 372 373 374 375 376 377 378 379 380 381 382 383 384 385

Describe and interpretpotential-energy curves for endothermic and exothermic reactions. Use theArrhenius equation. Define elementary reaction, reaction mechanism, and reaction intermediate. Write the overall chemical equation from a mechanism. Define molecularity. Give examples of unimolecular, bimolecular, and termolecular reactions. Determine the molecularity of an elementary reaction. Write the rate equation for an elementary reaction. Explain therate-determining step of a mechanism. Determine the rate law from a mechanism with an initial slow step. Determine the rate law from a mechanism with an initial fast, equilibrium step. Describe how acatalyst influences the rate of a reaction. Indicate how a catalyst changes the potential-energy curve of a reaction. Definehomogeneous catalysis andheterogeneous catalysis. Chemical Equilibrium Definedynamic equilibrium andchemical equilibrium. Apply stoichiometry to an equilibrium mixture. Define equilibrium-constant expression and equilibrium constant. State the law of mass action.

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386 Write equilibrium-constant expressions. 387 Describe the kinetics argument for the approach to chemical equilibrium. 388 Obtain an equilibrium constant from reaction composition. 389 Describe the equilibrium constantK p ; indicate howK p andK c are related.

ObtainK c for a reaction that can be written as a sum of other reactions of 390 knownK c values. 391 Define homogeneous equilibrium and heterogeneous equilibrium. 392 WriteK c for a reaction with pure solids or liquids. 393 Give a qualitative interpretation of the equilibrium constant based on its value. 394 Define reaction quotient, Q. 395 Describe the direction of reaction after comparing Q withK c . 396 Use the reaction quotient. 397 Obtain one equilibrium concentration given the others. 398 Solve an equilibrium problem (involving a linear equation inx ). 399 Solve an equilibrium problem (involving a quadratic equation inx ). 400 State Le Chteliers principle.
401 402 403 404 405 406 407 408 409 410 411 412 413 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430

State what happens to an equilibrium when a reactant or product is added or removed. Apply Le Chteliers principle when a concentration is altered. Describe the effect of a pressure change on chemical equilibrium. Apply Le Chteliers principle when the pressure is altered. Describe the effect of a temperature change on chemical equilibrium. Apply Le Chteliers principle when the temperature is altered. Describe how the optimum conditions for a reaction are chosen. Define catalyst. Compare the effect of a catalyst on rate of reaction with its effect on equilibrium. Describe how a catalyst can affect the product formed. Acids and Bases Defineacid andbase according to the Arrhenius concept. Defineacid andbase according to the BrnstedLowry concept. Define the termconjugate acidbase pair. Identify acid and base species. Defineamphiprotic species. DefineLewis acid andLewis base. Identify Lewis acid and Lewis base species. Understand the relationship between the strength of an acid and that of its conjugate base. Decide whether reactants or products are favored in an acidbase reaction. Note the two factors that determine relative acid strengths. Understand the periodic trends in the strengths of the binary acids HX. Understand the rules for determining the relative strengths of oxoacids. Understand the relative acid strengths of a polyprotic acid and its anions. Defineself-ionization (orautoionization). Define theion-product constant for water. Calculate the concentrations of H3O+and OH-in solutions of a strong acid or base.

DefinepH. Calculate the pH from the hydronium-ion concentration. Calculate the hydronium-ion concentration from the pH. Describe the determination of pH by a pH meter and by acidbase indicators. Acid-Base Equilibria Write the chemical equation for a weak acid undergoingacid ionization in aqueous 431 solution. 432 Defineacid-ionization constant anddegree of ionization.

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433 DetermineK a from the solution pH.

Calculate concentrations of species in a weak acid solution usingK a (approximation 434 method).
435

State the assumption that allows for using approximations when solving problems. Calculate concentrations of species in a weak acid solution usingK a (quadratic

436 formula). 437 State the general trend in the ionization constants of a polyprotic acid. 438 Calculate concentrations of species in a solution of a diprotic acid.

Write the chemical equation for a weak base undergoing ionization in aqueous
439 solution. 440 Definebase-ionization constant. 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 464

Calculate concentrations of species in a weak base solution usingK b . Write thehydrolysis reaction of an ion to form an acidic solution. Write the hydrolysis reaction of an ion to form a basic solution. Predict whether a salt solution is acidic, basic, or neutral. ObtainK a fromK b orK b fromK a . Calculating concentrations of species in a salt solution. Explain the common-ion effect. Calculate the common-ion effect on acid ionization (effect of a strong acid). Calculate the common-ion effect on acid ionization (effect of a conjugate base). Definebuffer andbuffer capacity. Describe the pH change of a buffer solution with the addition of acid or base. Calculate the pH of a buffer from given volumes of solution. Calculate the pH of a buffer when a strong acid or a strong base is added. Defineequivalence point. Describe the curve for the titration of a strong acid by a strong base. Calculate the pH of a solution of a strong acid and a strong base. Describe the curve for the titration of a weak acid by a strong base. Calculate the pH at the equivalence point in the titration of a weak acid by a strong base. Describe the curve for the titration of a weak base by a strong acid. Calculate the pH of a solution at several points of a titration of weak base by a strong acid. Solubility and Complex-Ion Equilibria Define thesolubility product constant ,K sp . Write solubility product expressions. Definemolar solubility. CalculateK sp from the solubility (simple example).

465 CalculateK sp from the solubility (more complicated example). 466 Calculate the solubility fromK sp . 467 468 469 470 471 472 473 474 475 476 477

Explain how the solubility of a salt is affected by another salt that has the same cation or anion. (common ion ) Calculate the solubility of a slightly soluble salt in a solution of a common ion. Defineion product. State the criterion for precipitation. Predict whether precipitation will occur, given ion concentrations. Predict whether precipitation will occur, given solution volumes and concentrations. Definefractional precipitation. Explain how two ions can be separated using fractional precipitation. Explain the qualitative effect of pH on solubility of a slightly soluble salt. Determine the qualitative effect of pH on solubility. Explain the basis for the sulfide scheme to separate a mixture of metal ions.

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478 Definecomplex ion andligand.

Defineformation constant orstability constant, K f , anddissociation constant, K d .

479 480 Calculate the concentration of a metal ion in equilibrium with a complex ion. 481 Defineamphoteric hydroxide. 482 Predict whether a precipitate will form in the presence of the complex ion.

Calculate the solubility of a slightly soluble ionic compound in a solution of the

483 complex ion.

Energetics
484 Defineinternal energy, state function, work, andfirst law of thermodynamics.

Explain why the work done by the system as a result of expansion or contraction
485 during a chemical reaction is -P V . 486 Relate the change of internal energy, U , and heat of reaction,q . 487 Defineenthalpy, H. 488 489 490 491 492 493 494 495 496 497 498 499 500 501 502 503 504 505 506 507 508 509 510 511 512

Show how heat of reaction at constant pressure,q p , equals the change of enthalpy, H. Definespontaneous process. Defineentropy. Relate entropy to disorder in a molecular system (energy dispersal). State thesecond law of thermodynamics in terms of system plus surroundings. State the second law of thermodynamics in terms of the system only. Calculate the entropy change for a phase transition. Describe how H -T S functions as a criterion of a spontaneous reaction. Definestandard entropy (absolute entropy) . State the situations in which the entropy usually increases. Predict the sign of the entropy change of a reaction. Express the standard change of entropy of a reaction in terms of standard entropies of products and reactants. Calculate S for a reaction. Definefree energy, G. Define thestandard free-energy change. Calculate G from H and S . Define thestandard free energy of formation, DG . Calculate G from standard free energies of formation. State the rules for using G as a criterion for spontaneity. Interpret the sign of G . Relate the free-energy change to maximum useful work. Describe how the free energy changes during a chemical reaction. Define thethermodynamic equilibrium constant, K. Write the expression for a thermodynamic equilibrium constant. Indicate how the free-energy change of a reaction and the reaction quotient are related. Relate the standard free-energy change to the thermodynamic equilibrium constant.

513 514 CalculateK from the standard free-energy change (molecular equation). 515 CalculateK from the standard free-energy change (net ionic equation). 516 517 518 519 520 521

Describe how G at a given temperature ( G T ) is approximately related to H and S at that temperature. Describe how the spontaneity or nonspontaneity of a reaction is related to each of the four possible combinations of signs of H and S . Calculate G andK at various temperatures. Thermochemistry State the law of conservation of energy. Define a thermodynamic system and its surroundings. Define heat and heat of reaction.

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522 523 524 525 526 527 528 529 530 531 532 533 534 535 536 537 538 539 540 541

542 543 544 545 546 547 548 549 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565

Distinguish between an exothermic process and an endothermic process. Define enthalpy and enthalpy of reaction. Explain how the terms enthalpy of reaction and heat of reaction are related. Explain how enthalpy and internal energy are related. Define a thermochemical equation. Write a thermochemical equation given pertinent information. Learn the two rules for manipulating (reversing and multiplying) thermochemical equations. Manipulate a thermochemical equation using these rules. Calculate the heat absorbed or evolved from a reaction given its enthalpy of reaction and the mass of a reactant or product. Define heat capacity and specific heat. Relate the heat absorbed or evolved to the specific heat, mass, and temperature change. Calculate using this relation between heat and specific heat. Define calorimeter. Calculate the enthalpy of reaction from calorimetric data (its temperature change and heat capacity). State Hesss law of heat summation. Apply Hesss law to obtain the enthalpy change for one reaction from the enthalpy changes of a number of other reactions. Define standard state and reference form. Define standard enthalpy of formation. Calculate the heat of a phase transition using standard enthalpies of formation for the different phases. Calculate the heat (enthalpy) of reaction from the standard enthalpies of formation of the substances in the reaction. Electrochemistry Learn the steps for balancing oxidationreduction reactions in acidic solution using the half-reaction method. Balance equations by the half-reaction method (acidic solution). Learn the additional steps for balancing oxidationreduction reactions in basic solution using the half-reaction method. Balancing equations by the half-reaction method (basic solution). Defineelectrochemical cell, voltaic (galvanic) cell, electrolytic cell, andhalf-cell. Describe the function of thesalt bridge in a voltaic cell. State the reactions that occurs at theanode and thecathode in an electrochemical cell. Definecell reaction. Sketch and label a voltaic cell. Write the cell reaction from the cell notation. Definecell potential andvolt. Calculate the quantity of work from a given amount of cell reactant. Explain how the electrode potential of a cell is anintensive property. Definestandard cell potential andstandard electrode potential. Interpret the table of standard reduction potentials. Determine the relative strengths of oxidizing and reducing agents. Determine the direction of spontaneity from electrode potentials. Calculate cell potential from standard potentials. Calculate the free-energy change from electrode potentials. Calculate the cell potential from free-energy change. Calculate the equilibrium constant from cell potential. Calculate the cell potential for nonstandard conditions. Describe how pH can be determined using a glass electrode. Describe the construction and reactions of azinccarbon dry cell, alithiumiodine battery, alead storage cell, and anickel-cadmium cell.

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566 567 568 569 570 571 572 573 574 575 576 577 578 579 580 581 582 583 584 585 586 587 588 589 590 591 592 593 594 595 596 597 598 599 600 601 602

Explain the operation of a proton-exchange membranefuel cell. Explain the electrochemical process of the rusting of iron. Definecathodic protection. Defineelectrolysis. Learn the half-reactions for water undergoing oxidation and reduction. Predict the half-reactions in an aqueous electrolysis. Calculate the amount of charge from the amount of product in an electrolysis. Calculate the amount of product from the amount of charge in an electrolysis. Nuclear Chemistry Defineradioactive decay andnuclear bombardment reaction. Learn the nuclear symbols forpositron, gamma photon, electron, neutron, proton. Write a nuclear equation. Deduce a product or reactant in a nuclear equation. Describe theshell model of the nucleus. Explain theband of stability. Predict the relative stabilities of nuclides. List the six types of radioactive decay. Predict the type of radioactive decay. Defineradioactive decay series. Definetransmutation. Use the notation for a bombardment reaction. Locate thetransuranium elements on the periodic table. Determine the product nucleus in a nuclear bombardment reaction. Defineradioactive decay constant. Calculate the decay constant from activity. Definehalf-life. Draw a typical half-life decay curve of a radioactive element. Calculate the half-life from the decay constant. Calculate the decay constant and activity from half-life. Determine the fraction of nuclei remaining after a specified time. Apply the carbon-14 dating method. State the ways in which radioactive isotopes are used for chemical analysis. Calculate the energy change for a nuclear reaction. Properties of alpha,beta and gamma rays Definenuclear binding energy andmass defect. Compare and contrastnuclear fission andnuclear fusion. Explain how a controlledchain reaction is applied in anuclear fission reactor using acritical mass of fissionable material. Write the reaction of the nuclear fusion of deuterium and tritium.

Inorganic Chemistry
Chemistry of the Main-Group Elements
603 Note the low ionization energies and electronegativities of the metals. 604 Give the principal oxidation states of the main-group elements. 605 State the periodic trends in metallic characteristics. 606 607 608 609 610 611 612 613

Metals: Characteristics and Production Definemetal, alloy, mineral, andore. Definemetallurgy. State the basic steps in the production of a metal. Define theBayer process . Describe the roasting of lead sulfide ore. Describe the electrolysis of molten lithium chloride. Define theDow process. Define theHallHroult process.

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614 Describe the chemical reduction of lead(II) oxide to lead metal. 615 Give some methods for refining metals.

Bonding in Metals
616 Describe the electron-sea model of metals. 617 Describe the molecular orbital theory of sodium and magnesium metals. 618 619 620 621 622 623 624 625 626 627 628 629 630 631 632 633 634 635 636 637 638 639 640 641 642 643 644 645 646 647 648 649 650 651 652 653 654 655 656 657 658 659

Group IA: The Alkali Metals Note the reactivity of the alkali metals. Describe the metallurgy, reactions, and compounds of lithium. Describe the metallurgy, reactions, and compounds of sodium. Define theSolvay process. Describe some compounds of potassium. Group IIA: The Alkaline Earth Metals Describe the metallurgy, reactions, and compounds of magnesium. Describe the metallurgy, reactions, and compounds of calcium. Group IIIA and Group IVA Metals Describe the metallurgy, reactions, and compounds of aluminum. Define theGoldschmidt process. Describe the metallurgy, reactions, and compounds of tin and lead. Hydrogen Describe some properties of hydrogen. Describe the commercial preparation of hydrogen. Define thesteam-reforming process. Describe some reactions and compounds of hydrogen. Define abinary hydride. Group IVA: The Carbon Family Definecatenation. Describe some allotropes of carbon. Describe the chemical properties of the oxides of carbon. Describe the chemical properties of the carbonates. Describe the preparation of extremely pure silicon. Definesilica. Describe the uses of quartz. Definesilicate, condensation reaction, andsilicone. Group VA: Nitrogen and the Phosphorus Family Describe the properties and uses of nitrogen. Describe some nitrogen compounds. Define theOstwald process. Describe the allotropes of phosphorus. Describe the phosphorus oxides and the oxoacids of phosphorus. Definepolyphosphoric acids andmetaphosphoric acids. Group VIA: Oxygen and the Sulfur Family Describe the properties and preparation of oxygen. Describe some reactions of oxygen. Defineoxide, peroxide, andsuperoxide. Describe the allotropes of sulfur. Describe the production of sulfur. Define theFrasch process and theClaus process. Describe the sulfur oxides and oxoacids. Define thecontact process. Group VIIA: The Halogens Describe chlorine and its properties, preparation, and uses. Describe the preparation of hydrogen chloride and its uses. Describe the preparation and uses of the oxoacids of chlorine. Group VIIIA: The Noble Gases Describe the discovery, preparation, and uses of the noble gases. Describe some compounds of the noble gases.

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The Transition Elements and Coordination Compounds Periodic Trends in the Transition Elements Identify thetransition elements on the periodic table. State the three characteristics that set the transition elements apart from the maingroup elements. Write electron configurations of the transition elements. Describe trends in atomic radii of the transition elements. Learn the common oxidation states of the fourth-period transition elements. The Chemistry of Two Transition Elements Learn some of the common chromium compounds and their chemistry. Learn some of the common copper compounds and their chemistry. Formation and Structure of Complexes Definecomplex ion, complex (coordination compound) ligand, and coordination number. Give examples of amonodentate ligand, bidentate ligand, andpolydentate ligand. Naming Coordination Compounds
669 Learn the four rules for naming coordination compounds. 670 680 681 682 683 684 685 686 687 688 689 690 691 692 693

660 661 662 663 664 665 666

667 668

Write the IUPAC name given the structural formula of a coordination compound. Write the structural formula given the IUPAC name of a coordination compound. Structure and Isomerism in Coordination Compounds Defineconstitutional isomers, stereoisomers , andgeometric isomers. Decide whether geometric isomers are possible. Defineenantiomers (optical isomers ). Explain how structures are used to determine if an isomer ischiral. Describe how enantiomers areoptically active. Definedextrorotatory, levorotatory, andracemic mixture. Decide whether optical isomers are possible. Extractive Metallurgy Carbon Reduction Method Self Reduction Method Electrolytic reduction Method Cyanide Process Principles of Qualitative Analysis Group I to V as mentioned in the syllabus Nitrates, Halides ( excluding florides ), Sulphates and Sulphide

Organic Chemistry
Fundamentals of Molecular Structure and Chemical Reactivity Sketch the 1s, 2s and 2p atomic orbitals (with mathematical signs) and write the electronic configuration for all elements in the first two rows of the periodic chart. Show in a sketch how the sp3, sp2 and sp hybrid orbitals may be constructed from the
695 simple atomic orbitals.

694

Explain the bond angle for the hydrides of all the elements through F using both the
696 VSEPR and hybridization models. 697 Deduce molecular formula from composition and molecular weight. 698 Calculate the formal charge on an atom in a small molecule.

Predict the direction and relative magnitudes of the dipole moments of simple
699 molecules.

Sketch a reasonable set of molecular orbitals for any 2-carbon molecule, showing the
700 mathematical signs of the lobes and approximate relative energies.

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Describe the molecular events occurring during melting and boiling for ionic and
701 covalent compounds and molecular crystals like diamond.

Predict the relative solubilities, melting points, boiling points and relative acidities and basicities of simple compounds and explain your choice with reference to 702 structure.
703 704 Identify the major functional groups and types of reactions. 705 and Ka.

Explain by words and equations the factors affecting the rate of a chemical reaction.

Calculate the pH of a solution of a weak acid or base from the analytical concentration Calculate the concentrations of components in a chemical equilibrium from the
706 equilibrium constant and analytical concentrations.

The Alkanes and Cycloalkanes: Nomenclature, Conformation and Configuration Name by the IUPAC system any saturated hydrocarbon whose parent chain contains 10 or fewer carbon atoms and no more than two simple rings (or sketch the 707 hydrocarbon given its IUPAC name). Sketch the conformations of ethane, propane, butane, cyclobutane, cyclopentane and cyclohexane and simple substituted compounds derived from them. Describe (graphically ) the relation between conformation and potential energy for ethane, propane and butane and closely related compounds (Newman projections). Describe (graphically) the relation between conformation and potential energy for
710 cyclohexane.

708

709

711 712 713 714 715 716 717 718 719 720

Calculate the relative energies of disubstituted (e.g. methyl) cyclohexanes, assuming chair conformations and using the relative energies of monosubstituted cyclohexane or butane. Define and recognize stereoisomer, enantiomer, diastereomer, conformation, configuration, meso, epimer, resolution. Given their structures, state whether 2 compounds are enantiomers or diastereomers or some other kind of isomer. Predict the number of stereoisomers of a compound of known bonding. Sketch a molecule with a chiral center so as to show unambiguously the configuration using both Fisher projection and perspective drawing. Predict from the structure whether a pair of stereoisomers can be interconverted by a conformational change and thus might not be separable. Draw conclusions about the mechanism of a reaction from the stereochemistry. Given a proposed mechanism for a reaction, predict the stereochemistry. Outline a synthesis (several steps) of a hydrocarbon using halogenation and metal reductions. Outline syntheses of cyclopropane compounds using carbene-generating compounds. The Alkenes, Alkadienes and Alkynes ALKENES Sketch the molecular orbitals (bonding and antibonding) for ethene and their relative energies. Name by the IUPAC system any alkene whose parent chain contains 10 or fewer carbon atoms and sketch the alkene given its IUPAC name. Define, recognize and name alkene diastereomers (cis/trans); predict the direction of the difference in their physical properties and chemical stability. Outline the synthesis of a given alkene from an alkyl (di)halide, alcohol, alkyne or alkane (including stereochemistry). Write chemical equations to describe the currently accepted mechanism(s) of dehydrohalogenation of an alkyl halide (including stereochemistry). Explain how this mechanism is deduced from the experimental data.

721 722 723 724

725

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Write chemical equations to describe the currently accepted mechanism(s) of dehydration of an alcohol (including stereochemistry). Explain how this mechanism is 726 deduced from the experimental data.
727 728 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5). 729 Predict the alkenes formed by elimination reactions of given starting materials.

Describe the evidence for the existence of carbocations and their relative stabilities.

730 731

732

733

734 735 736

737 738 739

Predict the products or use in a synthetic plan the following reactions of alkenes (including stereochemistry): catalytic hydrogenation, addition of halogen and hypohalite, addition of hydrogen halide, addition of water, oxymercuration, addition of carbocations (polymerization and alkylation), hydroxylation, epoxidation, addition of carbenes, hydroboration, ozonolysis. Use the molecular formula, and oxidation and reduction reactions to deduce structural features of an alkene. Write chemical equations to describe the currently accepted mechanism of addition of halogens to alkenes (including stereochemistry). Explain how the mechanism is deduced from the experimental data. Write chemical equations to describe our current understanding of the mechanism of addition of acids (HX, H3O+, H2SO4) to alkenes. Explain how the mechanism is deduced from the experimental data. Using a reasonable mechanism for the reaction, explain why the orientation of addition of HBr is sometimes "anti-Markovnikov" and what experimental evidence exists for the explanation. Write the mechanism for the acid-catalyzed addition of an alkene to itself. Do the same for free radical addition. Write the mechanism for the Wurtz reaction and decarboxylation reaction CONJUGATED ALKENES -- DIENES Use allylic halogen substitution as part of a synthetic outline, (distinguish conditions yielding ionic addition and free-radical substitution). Write contributors to the resonance hybrid for simple systems such as allyl radical (cation), carbonate, nitro. Sketch the pi molecular orbitals of butadiene and allyl and indicate their relative energies in a sketch. Predict the products, in order of relative amount, of the addition of halogen or acid to a diene; give an explanation of the effect of temperature on the product distribution. By considering the mechanism and the stabilities of intermediates, explain the differences between the reactions of conjugated double bonds and isolated double bonds. Outline the mechanism and stereochemistry of the Diels-Alder reaction ALKYNES Predict the products and use in a synthetic scheme the following reactions of alkynes: addition of hydrogen, halogen, hydrogen halides, water, boron hydrides, and salt formation with very strong base or reducing metals. Outline a synthesis of an alkyne from an alkene, alkyl halide, dihalide or tetrahalide; outline the synthesis of an internal alkyne from a terminal alkyne. Reactions of Alkenes and Alkynes with KMnO4 and ozone Preparation of Alkenes and Alkyne by elimination reaction , Electrophilic reaction Predict products and stereochemistry of a Diels-Alder reaction. Make a sketch of a

740

741 742

742 743 744

745 746 Preparation of Alkyne by addition reaction

747 reasonable transition state for this reaction.

Alkyl Halides Name any alkyl halide whose parent chain is 10 carbons or less by the IUPAC system 748 and sketch an alkyl halide given its IUPAC name or alkyl name.

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Write the mechanism for halogenation of methane. Describe the experiments from which the mechanism was deduced and the reasoning which lead to the mechanism. Calculate bond dissociation energies and heats of reaction given the energies for various steps and draw mechanistic conclusions from this energy data (similarly heats of activation). Given energy data (or relative rate data) and other experimental information about a reaction, sketch a graph of energyvs. reaction progress. Predict the products (including order of abundance) of halogenation of an alkane and explain your choice by reference to the mechanism. Explain the difference between a transition state and an intermediate. Explain the greater selectivity achieved in bromination compared to chlorination. Use the existing experimental evidence to describe the basis of our current understanding of the mechanisms of nucleophilic substitution at sp3 carbon. Write chemical equations to outline the mechanism for a particular halide. Use nucleophilic substitution in a synthetic plan of several steps, taking into consideration elimination, rearrangement and stereochemistry. Note that some of these reactions form carbon-carbon bonds. Predict the products, including stereochemistry, of a nucleophilic substitution of an alkyl halide. Predict (and explain) the effect of alkyl, vinyl and aryl substituents on nucleophilic substitution. Given the identity of nucleophile, leaving group, substrate and solvent, predict whether elimination or substitution will predominate for a particular alkyl halide substrate. Outline in chemical equations the mechanisms of elimination of alkyl halides. Describe the experimental information collected about this reaction and how the mechanisms are deduced from this information. Define and use correctly the terms SN2, SN1, E2, E1. Outline syntheses using organomagnesium and organocopper compounds. Draw conclusions about the mechanism of a reaction from the stereochemistry. Given a proposed mechanism for a reaction, predict the stereochemistry. Given the predominant diastereomer in a stereoselective or stereospecific reaction, provide a mechanistic explanation for the preference. Describe the evidence for the existence of carbocations and their relative stabilities. Alcohols and Ethers ALCOHOLS Name any alcohol whose parent carbon chain consists of 10 or fewer atoms by the IUPAC system and sketch the alcohol given its IUPAC name or carbinol name. Predict the relative acidity of alcohols by referring to the stability of all species in the
769 equilibrium.

749

750 751 752 753 754

755

756 757 758

759

760 761 762 763 764 765

766 767 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5).

768

Using our current understanding of the mechanisms of the two addition reactions, explain why simple acid- catalyzed addition of water can give a different product in both stereochemistry and orientation from the hydroboration-oxidation. Note that the oxymercuration (Hg(OAc)2) / reduction is more regioselective than simple acid770 catalyzed addition of water. Show how the mechanism of the hydroboration reaction is deduced from the experimental data about the reaction. Write chemical equations to describe the 771 mechanism, showing transition states if necessary. Write a reasonable mechanism for the Grignard and lithium aluminum hydride 772 synthesis of alcohols from carbonyl compounds.

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Outline a several-step synthesis involving preparation of an alcohol from an alkene (two ways), a ketone or aldehyde, an alkyl halide, an ester, an epoxide or an ether. Outline the currently accepted mechanisms of the substitution of an alcohol by halogen
774 using HX and describe the experimental evidence for the mechanism.

773

Use HX and thionyl chloride or the phosphorus halides for the conversion of an alcohol
775 to an alkyl halide in a synthetic plan (the differences may be important).

Use the oxidation reactions of alcohols to aldehydes, ketones and carboxylic acids in a
776 synthetic plan.

777

Given all the reagents and products in an alcohol oxidation by dichromate or permanganate, determine the number of moles of each ingredient, i.e. balance the equation. Outline the mechanism of the oxidation of an alcohol by chromate.

Aromatic Compounds STRUCTURE and NOMENCLATURE Explain the unusual stability of conjugated double bond systems by the valence bond (resonance) and the molecular orbital (Huckel, aromaticity) methods; distinguish the 778 two approaches. Write contributor structures to the resonance hybrid for simple molecules (e.g. allyl radical, butadiene, benzyl cation, vinyl ether,p-nitrophenol) and order the structures 779 in decreasing importance as contributors. Explain the experimental basis for the concept of resonance or aromaticity, i.e. the differences in properties between aromatic and similar non-aromatic compounds. Sketch the molecular orbitals computed by the Huckel method for benzene, butadiene,
781 and allyl; assign relative energies.

780

782 783

784 785

Predict whether a molecule will be aromatic or antiaromatic (for single and condensed rings, ions, and heterocycles). Prerequisite: determine if the concept of aromaticity is applicable. Use correctly the following terms: resonance, delocalized, resonance energy, hybrid, orbital, bonding, antibonding, non-bonding, aromatic, antiaromatic. Use the concept of resonance and/or aromaticity to account for polarity, basicity, acidity, etc. of benzene derivatives such as phenol, aniline, nitrobenzene, compared to non-conjugated analogs. Name by the IUPAC system compounds with substituted benzene rings (e.g.pnitroaniline) and sketch substituted benzenes given their IUPAC names. ELECTROPHILIC AROMATIC SUBSTITUTION

Write the mechanism of electrophilic substitution of benzene for nitration, halogenation, alkylation, acylation, protonation, and sulfonation, including production of the electrophile. Sketch contributors to the intermediate resonance-stabilized ion and the electrophiles. Give experimental evidence for the mechanism. 786 Explain, by referring to the mechanism of the reaction, the effect of a previous substituent on the reactivity and orientation of electrophilic aromatic substitution 787 (consider resonance, inductive and steric effects). Outline a several-step synthesis of a substituted benzene which requires careful choice of order of substitution to put the substituents in the correct orientation. This synthesis may involve, in addition to the reactions in 9, oxidation or reduction of a substituent or use of a protecting group (e.g. acyl) and the choice of mild conditions for 788 substitution of aniline and phenol. Explain the ease with which substitution and elimination reactions occur at the carbon 789 to a benzene ring by application of the principles of resonance. NUCLEOPHILIC AROMATIC SUBSTITUTION Outline the mechanism of nucleophilic aromatic substitution and describe the 790 experimental evidence for our current understanding of the mechanism.

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Predict and explain the relative reactivity of substituted aryl halides toward
791 nucleophilic substitution by deduction from the mechanism of the reaction. 792 Use nucleophilic aromatic substitution as a step in synthetic sequence.

793

From the experimental evidence, explain why nucleophilic aromatic substitutions in the presence of very strong bases (like NH2-, C6H5-) proceed by elimination followed by addition rather than through an anionic intermediate (benzyne). MISCELLANEOUS Outline a synthesis using the preparation of a benzenediazonium salt and its substitution by halogen, hydrogen, cyanide, hydroxide with the correct reagents, and the conversion of a diazonium salt into an azo dye. See Unit XI. Outline the synthesis of salicylic acid from phenol. Use the oxidation and reduction of aromatic rings in a synthesis. Identify likely cumulative toxins among aromatic compounds. Carboxylic Acids and Their Derivatives Name by the IUPAC system any carboxylic acid, ester, amide or anhydride with 10 or fewer carbon atoms in the parent chain and sketch the above given their IUPAC names (and common names up to 4 carbons).

794 795 796 797

798

Analyze the causes of the relative acidities of carboxylic acids by considering the inductive, resonance and steric effects on the neutral (conjugate acid) form and the anionic (conjugate base) form; use a similar analysis to predict the acidities of others. Similarly analyze phenols, alcohols and compare with carboxylic acids 799 Outline the synthesis of a given carboxylic acid from the appropriate alcohol, aldehyde, methyl ketone, alkyl benzene, alkyl (aryl) halide, nitrile, amide, ester, anhydride, acyl 800 halide. Outline the synthesis of an acyl halide, amide, substituted amide, ester (lactone) or anhydride from a carboxylic acid directly or from acyl halide or anhydride or ester.

801

Outline the synthesis of compounds with the following functional groups from carboxylic acids or their derivatives: alcohol (p,s,t), -haloacid, -aminoacid, ketone, 802 aldehyde. 803 Describe and recognize lipids, phospholipids, soaps, nylon, proteins, polyesters. Write the currently accepted mechanism for the acid-catalyzed hydrolysis of ester, amide, anhydride or acyl halide to the corresponding carboxylic acid. Similarly basecatalyzed hydrolysis. Explain the experimental basis for each mechanism. Write the currently accepted mechanism for the acid-catalyzed preparation of an ester from an acid and an alcohol and explain the experimental evidence from which it was deduced. Write the currently accepted mechanism for acid or base-catalyzed ester exchange (transesterification) (exactly like hydrolysis and esterification). Outline the mechanism and stereochemistry of the Diels-Alder reaction, e.g. for maleic anhydride. Aldehydes and Ketones as Electrophiles Name any aldehyde or ketone which contains ten or fewer carbon atoms in its parent chain by the IUPAC system. Given alkanes, alkenes, alkyl halides, alcohols, ethers, carboxylic acids, ketones (aldehydes) of similar molecular weight, order them in polarity, boiling point, and solubility in water. Outline a synthesis of an aldehyde or ketone from a given alcohol, carboxylic acid, alkene, alkyne, or alkyl benzene (or a precursor of these). Write the currently accepted mechanism of Friedel-Crafts acylation of aromatic compounds and describe the experiments leading to this proposed mechanism. Write the currently accepted mechanisms for the addition of hydride reagents, Grignard reagents, (bisulfite) and cyanide ion to ketones and aldehydes.

804

805 806 807

808

809 810 811 812

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Write the currently accepted mechanisms for the addition of alcohols (and ammonia and its derivatives) to ketones and aldehydes; describe the experimental basis for these mechanisms, including the effect of pH. Show why some amines give imines and others 813 enamines. Advanced topic: Write the mechanism of the Cannizzaro reaction and describe the 814 experimental basis for the mechanism. Identify starting materials or products for the reactions of aldehydes and ketones with silver ion (in ammonia), permanganate, dichromate, cyanide, (bisulfite), ammonia, amines, hydrazine and its derivatives, alcohols, hydride reagents (at least two), hydrogen, and Grignard and other organometallic reagents. 815 Use organometallic reagents in the synthesis of compounds with new carbon-carbon 816 bonds. Use the reactions of aldehydes and ketones with oxidants, cyanide, ammonia and its 817 derivatives, alcohols, hydride and hydrogen in a short synthetic plan. Give a brief summary of the mechanism of the Wittig reaction and use the reaction in 818 a synthetic plan. Recognize an ylide. Carbonyl Compounds as Nucleophiles: Carbanions Write the currently accepted mechanisms for the acid-catalyzed and base-catalyzed 819 interconversion of keto and enol forms. Write the mechanisms for the base-catalyzed and acid-catalyzed halogenation of aldehydes and ketones and explain how the experimental evidence leads to these 820 mechanisms. Describe the mechanistic basis of the iodoform test. Write the mechanism of the aldol condensation for any simple reactive aldehydes or ketones. Describe the experimental evidence for this reaction mechanism. Recognize aldol condensation products and use the crossed aldol condensation in a
822 practical sythesis. 823 Write the currently accepted mechanism of the Claisen ester condensation.

821

Write the mechanism of formation of enamines and use them as an enol substitute in a synthetic sequence forming new C-C bonds, esp. one in which an enolate reaction 824 mixture would be too basic. Write the currently accepted mechanisms of the malonic and acetoacetic ester syntheses. Use these reactions in a synthetic plan, including that of a barbiturate. Write the mechanisms of the decarboxylation of -carbonyl acids and the base826 catalyzed reverse (Claisen) condensation of -dicarbonyl compounds.

825

Write the mechanism of and explain the reason for nucleophilic addition to the carbon of an , -unsaturated carbonyl compound, esp. by carbanions in the Michael 827 reaction.
828

Recognize products of a Michael reaction and use it in a simple synthetic scheme. Use the above reactions and the Reformatsky (PBr3 + carboxylic acid) and Hell-

829 Vollhard- Zelinski reactions in a short synthetic sequence.

Recognize reactions similar to the Aldol and Claisen condensations with functional
830 groups similar electronically to carboxyls.

Amines and Amino Acids Name any primary, secondary or tertiary aliphatic amine with 10 carbons or fewer in the parent chain by the IUPAC system and sketch the amine given its IUPAC name. 831 Name aniline, pyrrole, pyridine and their derivatives. Given a mixture of up to four organic compounds, outline their separation using a flow chart, by acid-base and solubility properties and by chemical reactions from which they 832 can be recovered.

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Analyze the causes of the relative basicities of a series of amines by applying the concepts of resonance, inductive and steric effects to explain the relative stabilities of base and conjugate acid and predict the relative basicity of another amine. Repeat using the acidities of the conjugate acids as your starting point (the way most chemists do it). Outline the synthesis of an amine using its preparation from a nitrile, nitro compound, alkyl halide, amide or ketone. The synthetic route must be chosen to minimize mixtures of primary, secondary and tertiary. Note that some synthetic methods change the number of carbon atoms in the molecule. Write the currently accepted mechanism for the preparation of amines from alkyl halides. Explain why this technique is particularly useful for the preparation of aminoacids. Why is the Gabriel synthesis often preferable? Give several examples of biologically important amines and amides. Recognize indole, quinoline, isoquinoline alkaloids and 2-arylethylamines. Advanced topic: Write the mechanism of the Hofmann degradation of amides to amines and comment on the experimental data leading to this complex mechanistic sequence.

833

834

835 836

837

Outline the steps in the (Hofmann) elimination of amines to form alkenes for identification. Given the product alkene and other spectroscopic and chemical 838 information, deduce the structure of the original amine. Outline the currently accepted mechanism of the formation of N-substituted amides from amines using experimental observations to support the mechanism.

839 840 Explain the high reactivity of aniline toward ring substitution. 841 Explain the chemical basis and practical use of the Hinsburg test.

Propose a mechanism for the reductive amination of a ketone or aldehyde using what you have already learned about reactions of carbonyl compounds and catalytic 842 reduction with hydrogen.
843

Outline simple syntheses of amino acids using reactions learned for amines and acids.

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