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JEE EXPERT
Carbonyl Compound
Batch...........
SINGLE OPTION CORRECT TYPE:
Q.1 Gem dihalide on hydrolysis gives:
(A) Vic diol (B) Gem diol (C) Carbonyl compound (D) Carboxylic acid

Q.2 In the given reaction:

OH OH
| |
CH 3  CH — C  CH 3 HIO
4  (a) + (b); (a) and (b) respectively be:
|
CH 3
(A) CH3CHO and CH3CHO (B) CH3COCH3 and CH3CHO
(C) CH3COCH3 and CH3COCH3 (D) CH3COOH and CH3COCH3

Q.3 Acetophenone can be obtained by the distillation of:

(A) (C6H5COO)2Ca (B) (CH3COO)2Ca
(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca

Q.4 Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction:
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III

Q.5 Acetal or ketal is:

(A) Vic dialkoxy compound (B) , -dialkoxy compound
(C) -alkoxy alcohol (D) Gem dialkoxy compound
Q.6 In the given reaction
O
|| ( i ) LiAlH 4
 (A)   
CH 3  CH 2  C  CH 2 COOC 2 H 5 [
X] 

( ii ) H 2O / H

O
||
CH 3  CH 2  C  CH 2  CH 2 OH  C 2 H 5OH
[X] will be:
CH 2  OH CH 2  OH
|  
(A) HCHO (B) + H (C) | + O H (D) HCN
CH 2OH CH 2  OH
Q.7 In the given reaction:
C 6 H 5  C  H NH OH / H 
 2  [X] [X] will be:
||
O
(A) Only syn oxime (B) Only anti oxime (C) mixture of syn and anti oxime (D) secondary amide
Q.8 Schiff's base is prepared from:
(A) Carbonyl compound and primary amine (B) Carbonyl compound and secondary amine
(C) Carbonyl compound and tertiary amine (D) All of these

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Q.9 Schiff's reagent is used for the differentiation between:
(A) HCHO and CH3CHO (B) CH3COCH3 and CH3CHO

O O
|| ||
(C) C6 H 5  CH 2  C  CH 3 and C6 H 5  C  CH 2  CH 3 (D) HCHO and C6H5CHO
Q.10 In the reaction sequence, [X] is ketone :
CH 3
 |
KMnO / O H / 
[X]  4  HOOC – (CH2)3– CH  COOH
[X] will be:

(A) (B) (C) (D)

Q.11 Which one of the following compounds will give dimethyl glyoxal with SeO2:
(A) Acetone (B) Acetophenone (C) Ethyl methyl ketone (D) Propanaldehyde
Q.12 In the given reaction

SeO
2  [X]; [X] will be:

(A) (B) (C) (D)

Q.13 Consider the given reaction :

O O
|| ||
; The above reaction is known as :
   CH 3  C  O  CH 3
C 6 H 5COOOH
CH 3  C  CH 3 
(A) Baeyer-villiger oxidation (B) Oppenaur oxidation (C) Periodate oxidation (D)Peroxide oxidation
Q.14 Acetone can be converted into pinacol by :
(A) Mg/Hg/H2O (B) Zn/Hg/HCl (C) Na/Hg/H2SO4 (D) All of these
Q.15 Arrange acidity of given four compounds in decreasing order:
O O O
|| || ||
(I) CH 3  C  CH 2  C  CH 3 (II) CH 3  C  CH 3 (III) CHCH (IV) CH3–CHO
Select correct answer from the codes given below:
(A) I > IV> III > II (B) I > IV > II >III (C) III > I > IV > II (D) II > IV > I > III
Q.16 In the given reaction
OH
|
X + Y 
NaOH
CH 3  CH  CH  CHO ; (X) and (Y) will respectively be:
5C |
CH 3
(A) CH3–CH2–CHO and CH3–CH2–CHO (B) CH3–CHO and CH3–CH2–CHO

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 CH 3
|
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH 3  C  CHO
|
CH 3
Q.17 Number of products in the given reaction :

C6H5CHO + CH3–CHO   Product will be
OH

(A) One (B) Three (C) Two (D) Four

Q.18 In the reaction :

/
H  [X];
O
+ [X] will be :

(A) (B) (C) (D)

Q.19 Product of Perkin reaction is:

(A) , -unsaturated aldehyde (B) -cyclohexyl , -unsaturated aldehyde
(C) -Aryl-, -unsaturated acid (D) All of these
Q.20 The product of the reaction:

NO2 CHO + (C6H5–CH2CO)2O

[X] will be :

(A) C6H5–CH =CH–COOH (B) NO2 CH=CH–COOH

(C) C6H5–CH=C–COOH (D) NO2 CH  C  COOH

|
C6 H 5

Q.21 In the given reaction

OH
|
C6H5CHO + X    C6 H 5  CH  CH 2  COOC 2 H 5 ;
(i ) Zn
[X] will be:
(ii ) HOH / NH 4Cl
(A) CH3–COOC2H5 (B) CH3–CH2–COOC2H5

(C) Br–CH2–COOC2H5 (D) CH–COOC2H5

Q.22 The given reaction
C6H5–CHO + Br–CH2–COOC2H5    C6H5–CH=CH–COOC2H5;
(i ) Zn
is known as :
(ii ) HOH / NH 4Cl
(iii ) 

(A) Perkin reaction (B) Knoevenagel reaction

(C) Reformatsky reaction (D) Claisen-Schmidt reaction
Q.23 Cross cannizzaro reaction is example of :
(A) Redox reaction (B) Disproportionation (C) Both (A) and (B) (D) Only oxidation

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 CH 2OH
|
Q.24 Acetaldehyde can be converted into HO CH 2  C  CH 2OH by which reagent?
|
CH 2OH
(A) KOH (B) KOH followed by LAH (C) excess of HCHO and KOH (D) KCN followed by SBH

Q.25 Metaformaldehyde is:

(A) Dimmer of HCHO (B) Trimer of formaldehyde
(C) Tetramer of formaldehyde (D) Polymer in which number of HCHO unit is more than 100
Q.26 In the given reaction :
O
|| Conc.H 2SO 4
CH  C  CH    [X]
3 3 Distillation
[X] will be :
(A) Methyl oxide (B) Phorone (C) 1, 3, 5-Trimethylbenzene (D) 2-Butyne
Q.27 Which will give silver mirror test with Tollens reagent :
(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D) All of these
Q.28 Which one of the combinations will give propanaldehyde on dry distillation?
(A) (C6H5COO)2Ca and (HCOO)2Ca (B) (CH3COO)2Ca and (CH3CH2–COO)2Ca
(C) (CH3–CH2–COO)2Ca and (HCOO)2Ca (D) (CH3COO)2Ca and (CH3COO)2Ca
Q.29 Grignard reagents do not give carbonyl compounds with :
(A) CO2 (B) RCOCl (C) RCN (D) RCOOR
Q.30 In the reaction sequence:
alc.KOH /  (i ) O
Cyclohexane hv  (X)     (Y)  (Z);
/ Cl 2
 (Z) will be :
3
(ii ) H 2O / Zn
(A) Hexanal (B) 2-Hexanone (C) 3-Hexanone (D) Hexanedial
Q.31 The given reaction

  
Aluminium tertiary butoxide
; is knows as :
Acetone

(A) Kolbe reaction (B) Tischenko reaction (C) MPV reaction (D) Oppeneur oxidation
Q.32 In the given reaction:
NaBH
H2C O  
4  (X)

(i) BH3 
(excess)
(ii) H2O2/OH

(Y)
(X) and (Y) are :

(A) CH2 OH and HO CH2 O

(B) CH3 O and HO CH2 O

(C) CH2 OH and HO CH2 OH

(D) CH2 OH and O

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Q.33 Cyanohydrin of which compound on hydrolysis will give lactic acid?
(A) C6H5CHO (B) HCHO (C) CH3CHO (D) CH3–CH2–CHO

Q.34 In the reaction sequence:

/
CH2OH–CHOH–CH2OH KHSO
 4 (X) 2 
( C H5O )3 Al
 (Y); (Y) will be:

(A) CH2=CH–CHO (B) CH2=CH–CH2OH (C) Mixture of CH2=CH–COOH and CH2=CH–CH2OH
O
||
(D) CH 2  CH  C  O  CH 2  CH  CH 2

Q.35 Acetaldehyde cannot give:

(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test

Q.36 The reaction in which NaCN/C2H5OH/HOH is used is:

(A) Perkin reaction (B) Benzoin condensation
(C) Reimer-Tieman reaction (D) Rosenmunds reduction

Q.37 Compound formed by the reaction of furfural ( ) with ethanol is

(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal

Question No. 38 to 40 (3 questions)

An alkene (A) C16H16 on ozonolysis gives only product (B) C8H8O. (B) also can be obtained by
hydrolysis of the product obtained by reaction between cyano benzene and CH3MgBr. (A) can show
geometrical isomerism and it can decolourise Br2 water. (B) on treatment with SeO2 produces (C).

Q.38 Which is not correct about (A)?

(A) A is optically inactive
(B) On catalytic hydrogenation 'trans' form of A produces racemic mixture
(C) A can be prepared by Witting reaction on acetophenone with Ph3P = C(CH3)Ph.
(D) On treatment with per acid followed by hydrolysis 'trans' form of A produces racemic mixture
Q.39 Which is not correct about B?
(A) It gives iodoform test
(B) On treatment with LiAlH4, H2O it produces a compound which also responds to iodoform test.
(C) It gives Tollen's test
(D) On treatment with NH2NH2, EtO– at high temperature it produces ethyl benzene

Q.40 Which is not correct about C?

(A) On treatment with NaBH4 it will produce a diol.
(B) On treatment with OH– (conc.) followed by acidification it produces an optically active acid.
(C) It gives Tollen's test
(D) It can take part in aldol condensation
Q.41 Questions given below consist of two statements each printed as Assertion (A) and Reason (R); while
answering these questions you are required to choose any one of the following four responses:
(A) if both (A) and (R) are true and (R) is the correct explanation of (A)
(B) if both (A) and (R) are true but (R) is not correct explanation of (A)
(C) if (A) is true but (R) is false
(D) if (A) is false and (R) is true
Assertion : Benzaldehyde with HCN gives two isomeric compounds
Reason : Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl group.
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Q.42 When D-glucose is treated with Br2 water then the product is:

(A) (B) (C) (D)

[( CH 3 )3 CO ]3 Al
Q.43 +     A. A is:

(A) (B)

(C) (D)

LiAlH 4
Q.44    product is

(A) CH2CH2CHO (B) CH=CHCH2OH

(C) CH2CH2CH2OH (D) CH2CH2CH2OH

Question No.45 to 49 (5 questions)

Compound 'C' CF3  C  C(CH 3 )3  was prepared in a three step sequence from ethyl trifluoroacetate.
 || 
 O 
 
The first step in a sequence involved treating ethyl trifluoroacetate with NH3 to give a compound A. A on
treatment with reagent 'X' (alongwith gentle heating) produces a compound B (which on hydrolysis can
produce an acid). B on treatment with an orango metallic, 'Y', followed by hyydrolysis produces C.
Based on above passing attempt the following questions:
Q.45 Structutre of 'A' would be
OH
C
(A) (B) (C) CF OCH2CH3 (D)
3
NH2
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Q.46 Structure of B would be
O
||
(A) CF3  C  NH 2 (B) CF3–CN (C) CF3–CH2–CN (D) CF3–CH2–NH2
Q.47 'X' should be
(A) BaO2 (B) H2O2 (C) P4O10 (D) N2O
Q.48 When 'C' is treated with perbenzoic acid it will produce
O O
|| ||
(A) CF3  C  O  C(CH 3 )3 (B) (CH 3 )3 C  C  OCF3

(C) CF3  C  OH (D) (CH3)3C–OH

||
O

H
Q.49 C D 
2
E : 'E' is :
Raney Ni

S
||
(A) (B) (C) (D) CF3  C  S  C(CH 3 )3

Q.50 What is X in the following reaction?

+ ( 
 X
i ) RO
(ii ) pOH

(A) (B) (C) (D)

O O
|| ||
Q.51 CH 3  C  H and CH 3  C  CH 3 is differentiated by
(A) Tollen's reagent (B) Fehling (C) Iodoform (D) NaHSO3

Q.52 A compound with molecular formula C8H18O4 does not give litmus test and does not give colour with
2,4–DNP. It reacts with excess MeCOCl to give a compound whose vapour density is 152. Compound
A contains how many hydroxy groups?
(A) 1 (B) 2 (C) 3 (D) 4
O
||
Cl3C  C  H  Cl3C – CH2OH + Cl3C – COONa
NaOH
Q.53 Statement-1 :
Statement-2 : There are no – H in this compound, so it can't give aldol.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.

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 Paragraph for Question Nos. 54 to 56
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed
by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes
intramolecular aldol reaction to give predominantly S.

P  Q   R 1  S

1. MeMgBr 1. O 3 . OH ¯
2. Zn , H O
2. H , H 2O 2.  2
3. H 2SO 4 , 
Q.54 The structure of the carbonyl compound P is [JEE 2009]
O
Me
(A) (B) (C) (D)
O Me O Me O Et
Me
Q.55 The structure of the products Q and R, respectively, are [JEE 2009]
O O

Me H H
(A) , COMe (B) , CHO
Me Me
Me Me Me Me Me Me
O Me O

H CH3
(C) , CHO (D) , CHO
Et
Me Me Et Me Et
Me
Q.56 The structure of the product S is [JEE 2009]
O

(A) (B)
O
Me Me
Me

O
O
Me
(C) (D)
Me Me

ANSWER KEY
Q.1 C Q.2 B Q.3 C Q.4 A Q.5 D Q.6 B Q.7 C
Q.8 A Q.9 B Q.10 B Q.11 C Q.12 B Q.13 A Q.14 A
Q.15 B Q.16 B Q.17 C Q.18 D Q.19 C Q.20 D Q.21 C
Q.22 C Q.23 A Q.24 C Q.25 B Q.26 C Q.27 D Q.28 C
Q.29 A Q.30 D Q.31 D Q.32 C Q.33 C Q.34 D Q.35 B
Q.36 B Q.37 D Q.38 D Q.39 C Q.40 D Q.41 C Q.42 A
Q.43 B Q.44 C Q.45 B Q.46 B Q.47 C Q.48 A Q.49 C
Q.50 B Q.51 A; B Q.52 C Q.53 D Q.54 B Q.55 A Q.56 B
Carbonyl Compound