ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

IIT JEE: 2015 CRASH COURSE (C-15) DATE:

TOPIC:KETONES

SECTIONI (Multiple Choice Questions)

This section contains 05 multiple choice questions. Each question has 4 choices (A),
(B), (C) and (D) for its answer, out which ONLY ONE is correct.

1. Which of the following carbonyl compounds reacts most rapidly with nucleophilic reagents?
(a) Benzaldehyde (b) 3,3 dimethylbutanal
(c) Acetophenone (d) 2,2 dimethylcyclohexanone

2. Which of the following amines would be best chosen for preparing an enamine derivative from
cyclohexanone?
(a) Dimethylmine (b) Ethylamine (c) Trimethylamine (d) Hydroxylamine

3. Which reaction or sequence of reactions would be best used to convert cyclohexanone to cis -1,2
cyclohexanediol?
(a) PCC in CH 2 Cl2 and base
(b) (i) NaBH 4 (ii) H 3 PO 4 &heat(iii) OsO 4 in pyridine
(c) (i) NaBH 4 ; (ii) H 3 PO 4 & heat;(iii) C6 H 5CO3 H
(d) (i) NaBH 4 ; (ii) OsO 4 in pyridine

4. Isolable hydrates are formed by

(a) CF3COCH 3 (b) PhCOPh (c) ( Me3C )2 CO (d) CH 3COCH 3

5. The product of the following reaction is

OH
Pb(OAc)4

OH
O O
O
O O

(a) O (b) (c) O (d) O

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 SECTION-II (Multiple Choice Questions)
This section contains 3 multiple choice questions. Each question has 4 choices (A),
(B), (C) and (D) for its answer, out which ONE OR MORE is/are correct.

6. Following method(s) can not be used for the preparation of a ketone

(a) Passing of alcohol vapour over red hot copper
(b) Hydration of alkynes in presence of H 2SO 4 and HgSO 4
(c) Cleavage of 1, 3- diols with HIO 4
(d) Rosenmunds reduction

7. Dimethyl ketone can be prepared by

(a) Reaction of acetyl chloride with methyl magnesium chloride
(b) Reaction of acetyl chloride with dimethyl lithiumcuprate
(c) Reaction of acetyl chloride with dimethyl cadmium
(d) Reaction of methyl cyanide with methyl magnesium chloride followed by hydrolysis

8. The product(s) of the reaction of Ph ( CH 3 ) C ( OH ) C ( OH )( CH 3 ) Ph with BF3 is/are

(a) PhC ( CH 3 )2 COPh (b) Ph 2 C ( CH 3 ) COCH 3
(c) Ph 2 CCOC ( CH 3 )2 (d) CH 3OC6 H 4 COC6 H 4 OCH 3

SECTION III (Integer Answer Type)

This section contains 5 questions. The answer to each of the questions is a single
digit integer, ranging from 0 to 9. The correct digit below the question number in
the ORS is be bubbled.

9.

How many total chiral + geometrical centres will be there in the product?

10. A ( C4 H10 )
Br2

B
KOH

C
O3 H 2 O
D Product D does not give Tollens test but gives iodoform
test. How many carbon atoms are there in product D?

11. In the reaction

O
HO CH2 C CH3
How many distinct products (saturated) are possible?

12.

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 O
+
Ph CH3
The no. of stereoisomers shown by the product of the following reaction would be

13.
OH OH
CH3
Ph
How many final products are possible in the above sequence of reaction (including stereo)?

SECTION IV (Paragraph Type)

This section contains 2 multiple choice questions relating to 1 paragraph. Each
question has four choices (A), (B), (C) and (D) out of which ONLY ONE is correct.

Passage for (Que. No. 14 to 15)

Oxidation of saturated C-H groups
Methylene group adjacent to carbonyl groups can by oxidized with SeO 2 to give dicarbonyl
compounds. In case of unsymmetrical ketones, oxidation gemerally occurs at that CH 2 group which
is most readily enolized. Two mechanisms have suggested for this oxidation. In first, the selenate
ester of the enol is involved. In the second proposal the principal intermediate is a ketoselenic
acid. SeO 2 can also be used to oxidize allylic or benzylic C H bonds. However in this case the
product is alcohols. If the oxidation is carried out in acetic acid as the solvent and then acetate esters
are formed
14. Predict the product of the following reaction:
O

SeO2

O O

O OH
O O

(a) O (b) (c) O (d)

15. Oxidation of toluene by SeO 2 gives

(a) Benzyl alcohol (b) Benzaldehyde (c) Acetophenone (d) Benzophenone

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 SECTION - V (Matrix Match Type)
This section 1 Question. Each question has four statements Given in Column - I and
four statements in Column II. Any given statement in Column I can have correct
matching with one or more statement (s) given in column II.

16.
Column I Column II
(a) Benzilic Acid Rearrangement p. PhCOPh + NaOH
(b) CH 3CH ( CH 3 ) COCl CH 3CH ( CH 3 ) CHO q. Pd C (S or Quinoline)
(c) Rosenmund Reduction r. Lithium tri-t-butoxyaluminium
hydride
(d) Claisen Schmidt s. PhCHCH 3 + CH 3 COCH 3
t. PhCOCH 3 + ethanolic CN

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 ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI
TOPIC: KETONES
(ANSWER KEY) (C-15)

1 [b] 2 [a] 3 [b] 4 [a] 5 [d] 6 [cd] 7 [abcd]

8 [c] 9 [4] 10 [3] 11 [6] 12 [3] 13 [8]

14 [b] 15 [a] 16 [ a p; b q, r,;c q;d r ]

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