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1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. a. How many alkyl chlorides can be obtained from monochlorination of the following alkane?
A) B) C) D) b. A) B) C) D) E) c. A) B) C) D) E) d. A) B) C) D) E)
1 2 6 7 What is the major product obtained from the monobromination of 2,2,6trimethylheptane? 2-bromo-2,2,6-trimethylheptane 4-bromo-2,2,6-trimethylheptane 2-bromo-2,6,6-trimethylheptane 1-bromo-2,6,6-trimethylheptane 3-bromo-2,2,6-trimethylheptane How many structural isomers can be formed when 1,4-dimethylcyclohexane is monobrominated? 1 2 3 4 5 What product will be formed from the reaction of cis-1-bromo-4-methylcyclohexane with methoxide ion under SN2 conditions? trans- and cis-4-methylcyclohexanol trans-4-methylcyclohexanol trans-1-methoxy-4-methylcyclohexane cis-1-methoxy-4-methylcyclohexane trans- and cis-1-methoxy-4-methylcyclohexane
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e. A) B) C) D) E) f. A) B) C) D) E) g. A) B) C) D) E) h. A) B) C) D) E) i. A) B) C) D) E) j. A) B) C) D) E)
Which of the following alkyl halides is the most reactive in an SN2 reaction? 1-bromo-2,3-dimethylpropane 2-bromopropane 1-chlorobutane 1-bromo-2-methylpropane 1-bromobutane Which statement best describes a carbon-chlorine bond? The bond is covalent and polar, with chlorine carrying a partial negative charge. The bond is covalent and nonpolar. The bond is ionic and polar, with chlorine carrying a full positive charge. The bond is covalent and polar, with chlorine carrying a partial positive charge. The bond is ionic and polar, with chlorine carrying a full negative charge. Which of the following compounds has the best leaving group? an ether an amine an alcohol a protonated amine a protonated alcohol Which of the following is not a true statement? Tertiary alcohols undergo SN1 reactions with hydrogen halides. Primary alcohols undergo SN1 reactions with hydrogen halides. Secondary alcohols undergo SN1 reactions with hydrogen halides. Tertiary alcohols undergo E1 dehydration reactions. Secondary alcohols undergo E1 dehydration reactions. Which of the following anions is the strongest base? fluoride ion (F) acetate ion (CH3CO2) iodide ion (I) hydroxide ion (OH) amide ion (NH2) Which of the following is the poorest leaving group? water methoxide ion iodide ion bromide ion acetate ion Page 2 of 7
2. (40 points, 4 points each) SHORT ANSWER. Draw the structure, or write the word or phrase that best completes each statement or answers the question. a. What is the major organic product for the following reaction?
Br
KOtBu tBuOH
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e. Give the major product obtained when the following alkyl halide undergoes E2 elimination.
g. What compound is formed when propanol is treated with PCC (pyridinium chlorochromate) in dry methylene chloride solvent?
h. Give the following a systematic IUPAC name and indicate if it is a primary, secondary or tertiary alcohol.
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j. Draw the major product for the following reaction, if the reaction is carried out under conditions that favor an SN2 reaction. Draw the substituents on the framework provided.
H Br H3C H
NaOCH3 CH3OH
trans-1-bromo-4-methylcyclohexane
3. (10 points) Three alkenes are formed from the E1 elimination of the compound below. Give the structures of the alkenes, and rank them according to the amount that would be formed. (Ignore stereoisomers). 3-bromo-2, 3-dimethlypentane
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4. (10 points) Multistep synthesis: Select one of the following three products. Show how 1-butanol can be converted into any ONE of the following compounds. Provide a sequence of reactions to perform the transformation, showing the reagents and structures of all intermediates products. The synthesis must use the given starting material. You may use any other substrate materials and/or reagents.
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