ORGANIC CHEMISTRY

CLASS-XII
HOTS
1) Primary alkyl halide (A) C4H9Br reacted with alcoholic KOH to give compound (B). Compound (B) is reacted with HBr to
give (C) which is an isomer of (A). When (A) was reacted with Na metal it gave a compound (D) C8H18 that was different
than the compound when n-butyl bromide was reacted with sodium. Give the structural formula of (A) and write the
equations for all the reactions.

2) Compound ‘A’ with molecular formula C4H9Br is treated with aq KOH solution. The rate of this reaction depends upon
the concentration of the compound ‘A’ only. When another optically active isomer ‘B’ of this compound was treated
with aq KOH solution, the rate of reaction was found to be dependent on concentration of compound and KOH both.
a) Write down the structural formula of both compounds ‘A’ and ‘B’.
b) Out of these two compounds, which one will be converted to the product with inverted configuration?

3) A compound (A) reacts with thionyl chloride to give compound (B). (B) reacts with Mg to form a Grignard reagent
which is treated with acetone and the product is hydrolysed to give 2-methyl-2-butanol. What are (A) and (B)
compounds?

4) A compound (A) with molecular formula C4H10O on oxidation forms compound (B). The compound (B) gives positive
iodoform test and on reaction with CH3MgBr followed by hydrolysis gives (C). Identify (A), (B) and (C) and give the
sequence of reactions.

5) An ether (A) C6H14O when heated with excess of hot conc HI produced two alkyl halides which on hydrolysis form
compounds (B) and (C). Oxidation of (B) gave an acid (D) whereas oxidation of (C) gave a ketone (E). Deduce the
structural formula of (A), (B), (C), (D) and (E).

6) An organic compound A (C2H6O) reacts with sodium to form B with the evolution of H2 and gives a yellow compound C
when treated with I2 and NaOH. When heated with conc H2SO4 at 413K, it gives a compound D(C4H10O) which on
treatment with conc HI at 373K gives E. D is also obtained when B is heated with E. Identify A, B, C, D and E and write
equations for the reactions involved.

7) An organic compound with molecular formula C9H10O forms 2,4-DNP derivative reduces Tollen’s reagent and
undergoes Cannizzaro reaction. On vigorous oxidation it gives 1,4-Benzene dicarboxylic acid. Identify the compound.

8) An organic compound (A) with molecular formula C8H8O forms an orange red precipitate with 2,4-DNP reagent and
gives yellow precipitate on heating with I2 in the presence of NaOH. It neither reduces Tollen’s reagent or Fehling’s
solution nor does it decolourise Bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a
carboxylic acid (B) having molecular formula C7H6O2. Identify the compound (A) and (B) and explain the reactions
involved.

9) A compound (A) with molecular formula C5H8O2 is reduced to n-pentane on treatment with Zn-Hg/HCl. (A) forms a
dioxime with hydrolxylamine and gives a positive iodoform test and Tollen’s test. Identify the compound (A) and deduce
its structure.

10) An unknown aldehyde (A) on reacting with alkali give a β-hydroxyaldehyde , which loses water to form an
unsaturated aldehhyde 2-Butenal. Another aldehyde (B) undergoes disproportionation reaction in the presence of conc.
alkali to form products (C) and (D). (C) is an aryl alcohol with the formula C7H8O.
i) Identify A and B.
ii) Write the sequence of reactions involved.
iii) Name the product when B reacts with Zn-Hg and conc HCl acid.
11) A compound X C2H4O on oxidation gives Y C2H4O2. X undergoes haloform reaction. On treatment with HCN X forms a
product Z which on hydrolysis gives 2-hydroxypropanoic acid.
a) Write down the structure of X and Y.
b) Name the product formed when X reacts with dil NaOH.
c) Write down the equations for the reactions involved.

12) An organic compound (A) has characteristic odour. On treatment with NaOH it forms two compounds (B) and (C).
Compound (B) has molecular formula C7H8O which on oxidation gives back (A). The compound (C)is a sodium salt of an
acid. When (C) is treated with soda lime, it yields an aromatic hydrocarbon (D). Deduce the structure of (A), (B), (C) and
(D). Write the sequence of reactions involved.

13) A compound (A) on oxidation gives (B) C2H4O2. (A) reacts with dil NaOH and on subsequent heating forms (C). (C) on
catalytic hydrogenation gives (D). Identify (A), (B), (C) and (D) and write down the reactions involved.

14) An organic compound (A) has molecular formula C5H10O. It does not reduce Tollen’s reagent but forms an orange-
red precipitate with 2,4-DNP reagent. It forms a carboxylic acid (B) with molecular formula C3H6O2 when treated with
alkaline KMnO4, yellow precipitate on treatment with NaOH and I2. Under vigorous conditions on oxidation it gives
ethanoic acid and propanoic acid. Sodium salt of (B) gave a hydrocarbon (C) in Kolbe’s electrolytic reduction. Identify (A),
(B) and (C) and write the reactions involved.

15) A ketone (A) which undergoes haloform reaction gives compound (B) on reduction. (B) on heating with conc H2SO4
gives a compound (C) which forms mono-ozonide (D). (D) on hydrolysis in the presence of Zn dust gives only
acetaldehyde. Identify (A), (B), (C) and (D). Write down the reactions involved.

16) An organic compound (A) (C3H6O) is resistant to oxidation but forms compound (B) (C3H8O) on reduction which
reacts with HBr to form the bromide (C). (C) forms a Grignard reagent which reacts with (A) to give (D) C6H14O. Give the
structures of (A), (B), (C) and (D) and explain the reactions involved.

17) An alkene (A) on ozonolysis gives acetone and an aldehyde. The aldehyde is easily oxidised to an acid (B). When (B) is
treated with Br2 in the presence of phosphorus, it yields compound (C) which on hydrolysis gives a hydroxy acid (D). This
acid can also be obtained from acetone by the reaction with HCN followed by hydrolysis. Idenitify the compounds (A),
(B), (C) and (D).

18) The compound (A), C5H10O does not show Tollen’s test. On reacting with C2H5MgBr followed by hydrolysis, the
compound (B), C7H16O was obtained. The dehydration of (B) gives (C), which on ozonolysis gave diethyketone and
acetaldehyde. Identify (A) and (B) and explain the reactions involved.

19) An organic compound (A) C6H10O on reaction with CH3MgBr followed by acid treatment gives compound(B). The
compound (B) on ozonolysis gives compound (C), which is the presence of a base gives 1-acetylcyclopentane (D). The
compound B on reaction with HBr gives compound E. Write the structures of (A), (B), (C), (D) and (E). Show how is
formed from C?

20) An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative reduces Tollen’s reagent and
undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Idenitify the compound.

21) An organic compound contains 69.77% Carbon, 11.63% hydrogen and the rest is oxygen. The molecular mass of the
compound is 86. It does not reduce Tollen’s reagent but forms an addition compound with NaHSO3 and give positive
iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the
compound.

22) An organic compound (A) (Molecular formula C8H16O2) was hydrolysed with dilute H2SO4 to give a carboxylic acid(B)
and an alcohol (C) . Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives But-1-ene. Write equations
for the reactions involved.
23) An optically active amide (A) C5H11NO on acid hydrolysis gives an acid and ammonia. When (A) is treated with
bromine and alkali, a compound is obtained which on treatment with nitrous acid gives an optically active alcohol and
nitrogen. The alcohol gives positive iodoform test. What is the structure of (A) and show the reactions involved?

24) Compound (A) C6H12O2 on reduction with LiAlH4 yielded two compounds (B) and (C). The compound (B) on oxidation
gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E). The latter on catalytic
hydrogenation gave (C). The compound (D) was oxidised further to give (F) which was found to be a monobasic acid
(Molecular formula weight=60). Deduce the structure of (A), (B), (C), (D) and (E).

25) An aromatic compound (A) on treatment with aqueous NH3 and heating forms compound (B) which on heating with
Br2 and KOH forms a compound (C) of molecular formula C6H7N. Write the structures and IUPAC names of compounds
(A), (B) and (C).

26) An optically inactive compound (A) having molecular formula C4H11N on treatment with HNO2 gave an alcohol (B).
(B) on heating at 440 K gave an alkene (C). (C) on treatment with HBr gave an optically active compound (D) having the
molecular formula C4H9Br. Identify (A), (B), (C) and (D) and write down their structural formulae. Also write down the
equations involved.

27) An organic compound (A)C3H5N on boiling with alkali gives ammonia and sodium salt of an acid (B) (C3H6O2) . (A) on
reduction gives C3H9N which reacts with nitrous acid to give D(C3H8O). Give the structural formula of (A),(B), (C) and (D).

28) A compound X (C8H10O) upon treatment with alkaline solution of iodine gives a yellow precipitate. The filtrate on
acidification gives a white solid Y (C7H6O2). Write down the structures of X and Y and explain the formation of Y.

29) Identify (A) to (G) in the following reaction

CH3CH2NH2 HNO2 A PCl5 B KCN C Na, C2H5OH D
[O]

E [O] F 1) NH3 G
2) H2SO4

30) Fill in the blanks with reagents/organic compounds in the following sequence of reactions.
i) A NaOH/Br2 B NaNO2 /HCl C D, 0oC E H2/Pt C6H5-CH2-NH2

Fe/Cl2
F

ii) A conc HNO3 B Sn/HCl C CHCl3/KOH D H2/Pt E

conc H2SO4 Δ F

NHCOCH3
+ CH3COOH

iii) R-NO2 Sn/HCl A Br2 excess B NaNO2/HCl C H3PO2 D

0-5oC H2O
Br2/KOH