Carbonyl Compound

ENTHUSE
IIT CHEMISTRY
ORGANIC CHEMISTRY
CARBONYL COMPOUND
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CARBONYL COMPOUND
EXERCISE # I
Q.1 Arrange these compounds in decreasing order of reactivity for the nucleophilic attack.
(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.2 In the given reaction

O O
[X] (i) LiAlH 4
CH3–CH2–C–CH2COOC2H5 ¾¾¾® (A) ¾¾¾¾
(ii ) H O / H Å
® CH3–CH2–C–CH2–CH2OH+C2H5OH
2
[X] will be :
CH 2 - OH CH 2 - OH
| | 1
(A) HCHO (B) CH 2 - OH + H Å (C) CH 2 - OH + O H (D) HCN
Q.3 In the given reaction:

NH OH / H Å
C6 H 5 - C - H ¾¾ 2¾ ¾¾® [X]
||
O
[X] will be:
(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and anti oxime (D) Secondary amide
Q.4 In the reaction :

Q
/D
O
¾¾H¾ ® [X]
[X] will be :
OH O OH OH O
OH O
(A) (B) (C) (D)
Q.5 Number of aldol products (without counting stereoisomers) in the given reaction :
Q
OH
C6H5CHO + CH3–CHO ¾¾
¾® Product
will be :
(A) One (B) Three (C) Two (D) Four
C.O.: NAIVEDHYAM, Plot No. SP-11, Old INOX, Indira Vihar, Kota (Raj.) 324005 Ph. 0744-2799900 1
Q.6 In the given reaction
OH
|
NaOH
X+Y ¾¾¾
5°C
® CH 3 - CH - CH - CHO
|
CH 3
(X) and (Y) will respectively be :
(A) CH3–CH2–CHO and CH3–CH2–CHO (B) CH3–CHO and CH3–CH2–CHO
CH 3
|
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH 3 - C - CHO
|
CH 3
Q.7 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.8 Gem dihalide on hydrolysis gives :

(A) Vic diol (B) Gem diol
(C) Carbonyl compound (D) Carboxylic acid
Q.9 Acetal or ketal is:
(A) Vic dialkoxy compound (B) a, w-dialkoxy compound
(C) a-alkoxy alcohol (D) Gem dialkoxy compound
Q.10 In the given reaction :
OH
|
® C6 H 5 - CH - CH 2 - COOC 2 H 5
C6H5CHO + X ¾¾¾¾¾ (i) Zn
(ii) HOH / NH 4 Cl
[X] will be :
(A) CH3–COOC2H5 (B) CH3–CH2–COOC2H5
(C) Br–CH2–COOC2H5 (D) CH–COOC2H5
Q.11 Cross cannizzaro reaction is example of :

(A) Redox reaction (B) Disproportionation
(C) Both (A) and (B) (D) Only oxidation
CH 2OH
|
Q.12 Acetaldehyde can be converted into HOCH 2 - C - CH 2 OH by which reagent ?
|
CH 2OH
(A) KOH (B) KOH followed by LAH

(C) excess of HCHO and KOH (D) KCN followed by SBH
Q.13 Product of Perkin reaction is :
(A) a, b-unsaturated aldehyde (B) b-cyclohexyl a, b-unsaturated aldehyde
(C) b-Aryl-a, b-unsaturated acid (D) All of these
Q.14 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

O
||
CH 3 - C - CH 3 ¾¾¾¾ ¾
® [X]
Conc.H 2SO 4
Distillation
[X] will be :
(A) Methyl oxide (B) Phorone
(C) 1, 3, 5-Trimethylbenzene (D) 2-Butyne
Q.16 In the reaction sequence :

.KOH / D
Cyclohexane ¾hv
¾¾
/ Cl 2
¾® (X)¾alc
¾¾¾ ¾® (Y)¾¾¾¾
(i) O3
¾
(ii) H O/ Zn
® (Z)
2
(Z) will be :
(A) Hexanal (B) 2-Hexanone (C) 3-Hexanone (D) Hexanedial
Q.17 Grignard reagents can never give carbonyl compounds with :
(A) CO2 (B) RCOCl (C) RCN (D) RCOOR
Q.18 The given reaction :

C6H5–CHO + Br–CH2–COOC2H5 ¾¾¾¾¾ ® C6H5–CH=CH–COOC2H5
(i) Zn
(ii) HOH / NH Cl 4
(iii) D
is known as :
(A) Perkin reaction (B) Knoevenagel reaction
(C) Reformatsky reaction (D) Claisen-Schmidt reaction
Q.19 The product of the reaction :
O2N CHO + (C6H5–CH2CO)2O

C6H5–CH2COONa /
[X]
will be :
(A) C6H5–CH =CH–COOH (B) NO2 CH=CH–COOH
(C) C6H5 – CH = C – COOH (D) NO2 CH = C - COOH
|
CH3 C6H5
Q.20 Cyanohydrin of which compound on hydrolysis will give lactic acid ?

(A) C6H5CHO (B) HCHO (C) CH3CHO (D) CH3–CH2–CHO

NaBH4 (i) BH3
H2 C O (X) + (Y)
(ii) H2O/H (excess)
(X) and (Y) are :
(A) CH2 OH and HO CH2 O
(B) CH3 O and HO CH2 O
(C) CH2 OH and CH3 OH
(D) CH2 OH and O
Q.22 Acetaldehyde cannot give :
(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test
OCH2CH3
Q.23 Compound formed by the reaction of furfural ( ) with ethanol is :
CHOH O CHO
O
(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal
Q.24 The reaction in which NaCN/C2H5OH/HOH is used is :
(A) Perkin reaction (B) Benzoin condensation

(C) Reimer-Tieman reaction (D) Rosenmunds reduction
Q.25 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
Q.26 In the reaction sequence:
/D
CH2OH–CHOH–CH2OH ¾KHSO
¾ ¾4¾
(C2 H5 O)3 Al
¾® (X) ¾¾¾¾ D
¾ ® (Y)
(i)HNO /0 C
(Y) will be: 

(ii)Cu Cl / HC
(iii) NaOH/600

(iv) HNO3 / H 2S
(v) H / Pd/ EtO
(A) CH2=CH–CHO (vi) Ac O/ Pyri e(1eq.)
(i) Ag, 
(B) CH2=CH–CH2OH

(ii)Fetu

(iii)CH3 Cl/AlCl3
(iv) Zn  /HCl
(C) Mixture of CH2=CH–COOH and CH2=CH–CH2OH
(v)KMn , NaOH/
O
|| 

(D) CH 2 = CH - C - O - CH 2 - CH = CH 2
Carbocation involve n any step of
Q.27 Tollen'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
O
(1) NaBH4
Q.28 A+ B
(2) H2O
Identify relationship between A & B products ?

(A) Diastereoisomers (B) Enantiomers (C) Positional isomer (D) Identical
Q.29 In the reaction sequence

HSCH2CH2SH H2
O + A Ni, heat
B
H
the product (B) is :

S SH
(A) (B) (C) (D) S
S SH
Q.30 In the reaction
O
1. (CH3)2CuLi
+ A
2. H3O
the product (A) is :

CH3 OH O O H3C OH
(A) (B) (C) (D)

CH3 CH3 CH 3
H.O. 92, Rajeev Gandhi Nagar, Kota (R .) Mob. 97831 w.nucleuseducation.in
Q.31 Which of the following does not form a stable hydrate by the addition of H2O?
O
O O O O
(A) Ph—C—C—C—Ph (B) O (C) O (D)
O
Q.32 The conversion
O O
O
can be effected by using the reagent

Cl CO2H Cl CO3H
(A) Tollen's reagent (B) O3 (C) (D)

O
–
CH2 = CH2—C—CH3 + HCN OH
the major product is :

OH O
(A) CH2 = CH—C—CH3 (B) CNCH2CH2CCH3
CN
(C) CH2 = CH—COOCH3 (D) CH3CH(CN)COCH3
O O
NaOH CH3COOH
Q.34 (I) + Cl2 P (II) + Cl2 Q
1 : 1 1 : 1
(mole) (mole) (mole) (mole)
Organic product P & Q are respectively -
O O O O
Cl Cl Cl Cl
(A) , (B) ,
O O O O
Cl Cl Cl Cl
(C) Cl , (D) Cl , Cl
Q.35 The major product obtained in the reaction is
NaCN
HCN
O
(A) OH (B) (C) (D)
CN CN O O
CN
CN
Q.36 Total number of stereoisomers of major product (Q) are :

NaOH
CH3–CHO + 4HCHO –HCOONa (P) 2CH3–CHO
+
(Q)
H
(A) 0 (B) 4 (C) 8 (D) 2
Q.37 CH3CHO + NH2OH ® CH3CH = N—OH

The above reaction occurs satisfactorily at
(A) pH = 1 (B) pH = 4.5 (C) pH = 12 (D) any value of pH
Q.38 An organic compound (A), C5H10O, reacts with hydrazine to form a hydrazone derivative (B). The
hydrazone (B) on being heated with KOH at about 180ºC, gives n-pentane. The compound (A) does
not respond positively to Tollen's reagent and to the iodoform test. The compound (A) is
O O O OH
(A) (B) (C) (D)
H
Q.39 The compound having the highest dipole moment is :
O
(A) (B) O (C) O (D)
O
O O
(1) Excess MeMgCl conc.
Q.40 (A) H SO 'B' Identify 'B' product ?
(2) H2O 2 4
O O O O
(A) (B) (C) (D)
Question No. 41 to 43 (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.41 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.42 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 followed by alc. KOH at high temperature, it produces ethyl benzene
Q.43 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 racemic mixture of a carboxylic
acid is obtained
(C) It gives Tollen's test
(D) It can take part in aldol condensation
Question No.44 to 48 (5 questions)
Compound 'C' éCF3 - C - C(CH 3 )3 ù was prepared in a three step sequence from ethyl trifluoroacetate.
ê || ú
ê O ú
ë û
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 hydrolysis
produces C. Based on above passing attempt the following questions:
Q.44 Structutre of 'A' would be
O O
C C
(A) H2N OCH2CH3 (B) H2N CF3
OH
CF3 OCH2CH3
C
(C) CF3 OCH2CH3 (D) C
NH3 NH
Q.45 Structure of B would be

O
||
(A) CF3 - C - NH 2 (B) CF3–CºN (C) CF3–CH2–CN (D) CF3–CH2–NH2
Q.46 'X' should be

(A) BaO2 (B) H2O2 (C) P4O10 (D) N2O
Q.47 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
Q.48 C D ¾¾¾¾H2
Raney Ni
® E : 'E' is :
H CF3 S
CF3
(A) C (B) C
(CH3)3C (CH 3)3C S
OH
CF3 H S
||
(C) C (D) CF3 - C - S - C(CH 3 )3
(CH 3)3C H
(Question No. 49 & 50)

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
Q.49 Assertion : Benzaldehyde with HCN gives two isomeric compounds

Reason : Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl group.
O
|| NaOH
Q.50 Assertion : Cl3C - C - H ¾¾¾® Cl3C—CH2OH + Cl3C—COONa
Reason : There are no a–H in this compound, so it can't give aldol.
EXERCISE # II
Q.1 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2 / NaOH (B)NaSO3H (C) NaCN / HCl (D) 2,4-DNP
Q.2 An optically inactive alcohol (A) C6H12O is oxidized by MnO2 to produce optically inactive
carbonyl compound while reduction of (A) by H2/Ni produces optically active compound. Possible
structure(s) of alcohol is/are
(A) Hex-2-ene-1- ol (B) Hex-3-ene-2- ol
(C) 2-Methyl pent-2 - ene-1-ol (D) 3-Methyl pent-2 - ene-1-ol
Q.3 Consider the structure of given alcohol:

OH
|
C6 H 5 - C - CH 3
|
C2 H5
This alcohol can be prepared from:
O O
|| ||
(A) C6 H 5 - C - CH3 and C2H5MgBr (B) CH3 - CH 2 - C - CH 3 and C6H5MgBr
O O
|| ||
(C) C6 H 5 - C - C2 H 5 and CH3MgBr (D) C6 H 5 - C - Cl and C2H5MgCl
Q.4 Correct option(s) regarding following reaction sequence is/are :

HgSO Ba(OH)2 NaOH 6 Ag
CH3 – C CH H SO 4 P Q I2 R+S T
2 4
'X'
COOH
(A) T is homologue of 'X' (B) R is sodium salt of
COOH
(C) P can produce S with NaOI (D) R is sodium salt of
Q.5 Which of the following compounds will not give aldol condensation :
(A) Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde
(i ) Ph P
Q.6 (A) ¾¾¾ 3
(ii) BuLi
¾®
(iii) (B)
In above reaction (A) and (B) will respectively be
(A) & CH3CHO (B) CH3CH2Cl &
(C) & HCHO (D) & CH3CHO
Q.7 Stability of hydrates of carbonyl compounds depends on:
(A) Steric hindrance (B) Presence of –I group on gemdiol carbon
(C) Intramolecular hydrogen bonding (D) angle strain in carbonyl compound
Q.8 Which of the following can be used for protection of carbonyl group
(A) CH2OH–CH2OH / HÅ (B) CH2OH–CH2–CH2OH / HÅ
(C) HS–(CH2)3–SH (D) CH2OH–CH2–CHO
Q.9 Which of the following is/are example of 1,4-addition reaction

O O
|| ||
(A) CH 2 = CH - C - H ¾¾¾¾
(i) NaCN
(ii) H O
® (B) CH 2 = CH - C - H ¾¾¾
LAH
®
H 2 O / HÅ
2
CH =CH - CN
(C) + CH2(COOMe)2 ¾¾¾¾¾¾
3 3CH ONa / CH OH
® (D) ¾¾2¾ ¾ ¾
¾®
HÅ O 3 Base
Q.10 Which of the following(s) will form stable hemiketal :

O O
|| ||
(A) Ph - C - Ph (B) HO - (CH 2 ) 3 - C - CH 3
O O
||
(C) CH 2 OH - C - (CHOH) 3 - CH 2 - OH (D) OH–CH2–CH2–CH2–C–CH3
Q.11 Mixture of Ph–CHO & HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph–CHO (D) Reduction of Ph–CHO
Q.12 Final product in the given reaction sequence is :
O
PhMgBr i) H–C–H H2
CH3–CºCH + [A] [B] [C]
ii) H + Pd/BaSO4
OH H
(A) (B)
H H H OH
OH OH
(C) (D)
H H H H
Q.13 Consider the following reaction sequence.
1. O3
A NaOH
heat
B
2. Zn, H2O
The products (A) and (B) are, respectively,

OH O O OH
(A) and (B) and

O
OH OH
O O O
O OH
and OH
(C) and (D)
O O O
Q.14 Consider the following sequence of reactions.
O
HOCH2.CH2OH 1. LiAlH4.Et 2O
+ A + B
H 2. H3O
COOCH3
The products (A) and (B) are, respectively.
O OH O O O
(A) and (B) and

O
CH3OC COOCH3 COOCH3 CHO
O
O O O HO OCH2 CH2 OH OCH=CH2
(C) and (D) and
COOCH3 CH2OH COOCH3 CH2 OH

O
NaCN 2 H SO
4
A H O, heat B
H2SO4 2
The major product (B) is :

OH OH CN COOH
(A) COOH (B) CN (C) (D)
(CH3)2CHNO2 + HCHO NaOH
the major product is
NO2
(A) (CH3)2CHCH2ONO2 (B) (CH3)2C
CH2OH
(C) (CH3)2CH—CHNO2 (D) (CH3)2CH—CH—CH2 NO2

O O

H
1. C H MgBr H SO , heat 1. O3
Ketone A 2. H2 O5 B –H2 O4 C 2. Zn, H2O +
2 2 O
O
The ketone (A) is :
(A) (B) (C) (D)

O O O O

O O
Me
1. KOH, heat
+
2. H3O
the product (X) is :

O
Me COOH Me COOH Me
HO COOH Me
(A) (B) (C) (D)

HOOC HOH2C
O3
Q.19 Zn
(A) conc.KOH (B)
(1 mole)
End product (B) of above reaction is :
+
CHO CO2– K
+
CH2OH CO–2 K
(A) (B) (C) (D) +
CH2OH CH2 OH CH2OH CO2– K
O
H+
+ C3H8O2 ( 1eq.) ¾¾® P¾¾¾¾
(i) N 2H 4 HCHO(excess) +
Q.20 1 ® Q ¾¾
H3 O
® R¾¾¾¾¾
Ba (OH)2
¾ ®S ;
Optically inactive diol (ii) O H / D
O
Final product 'S' is -
OH OH
OH OH
OH OH
(A) (B)
HO
HO HO HO
OH HO
OH
OH OH OH OH
OH
(C) (D)
HO OH OH HO
Q.21 Which of the following reactions will give(s) 2º alcohol as a major product :
O O
(i) LAH (i) CH3MgX(excess)
(A) CH3—CH2—C—NH2 (ii) NaNO /HCl (B) H—C—OR +
2 (ii) H
O
(i) RMgX CH3MgX (excess)
(C) H3C—HC—CH2 +
(D) CH3—C—Cl +
(ii) H H
O
Q.22 Match list-I with list-II ¾

List-I List-II
Q Q
(A) C6H5CHO+HCHO ¾O¾H
¾® C6H5CH2OH + HCO O (P) Cannizzaro reaction
O
–
OH
(B) CH3–C–H CH3–CH=CH–CHO (Q) Aldol condensation
O O OH O
–
(C) Ph–C–C–Ph OH (R) Soda-lime Decarboxylation
H 2O
Ph – C – C – OH
Ph
COONa
NaOH /CaO/ D
(D) ¾¾¾¾¾ ® (S) Benzil benzilic acid rearragement
Q.23 Match list-I with list-II
List - I List - II
NaBH 4
(A) CH2=CH–CHO ¾¾ ¾ ¾® (P) Acetal
Å
(B) C6H5CHO + Ph–NH2 ¾H¾®
¾ (Q) Schiff's base
OH
(C) C6H5COCH3+CH3–CH2–NH2 ¾¾® HÅ (R) CH3–CH–CH2
¾
Å
(D) RCHO + 2RCH2OH ¾H¾®
¾ (S) Imine
EXERCISE # III
Q.1 Predict the product of the reaction of propanal with each of the following :
(a) Methylmagnesium iodide, followed by dilute acid.
(b) Sodium acetylide, followed by dilute acid
(c) Phenyllithium, followed by dilute acid.
(d) Methanol containing dissolved hydrogen chloride
(e) Ethylene glycol, p-toluenesulfonic acid, benzene
(f) Aniline (C6H5NH2)
(g) Dimethylamine, p-toluenesulfonic acid, benzene
(h) Hydroxylamine
(i) Hydrazine
(j) Product of part (i) heated in triethylene glycol with sodium hydroxide
(k) p-Nitrophenylhydrazine
(l) Semicarbazide
(m) Sodium cyanide with addition of sulfuric acid
(n) Chromic acid
Q.2 Give structure for the products of the reaction when butanal is treated with each of the following reagents
Q
(a) [Ag(NH3)2]OH then HOH / HÅ (b) O H / HOH ,D
(c) NH2OH / H Å (d) C6H5Li then HOH
Q
(e) C6H5CHO, O H , D (f) CH º CNa then HOH / H Å
(g) CH2OH–CH2OH, HÅ (h) SH–CH2–CH2–CH2–SH then Raney Ni/H2
(i) CH3MgBr then H2O (j) HCN
(k) NaBH4
Br
|
(l) CH 3 – CH 2 - CH - COOC2 H 5 and Zn then H2O/ H Å
Q.3 Column - I Column - II

O
HCN LiAlH4 NaNO2

(A) traces of KOH
(A) (B)
HCl
(C) (P) Formation of six member ring takes place
O
Conc. H2SO4
(B) (A) (B) (Q) Final product is Ketone
O O
HO
(C) CH3 – C – CH2 – CH2– CH2– C – H D (A) (R) Final product formed will give positive
Idoform test
Ph
Å
(D) H
D
(A) (S) Final product formed will react with
CH3
OH OH
2,4-DNP. (2,4-Di-nitrophenyl hydrazine)
Q.4 Arrange the following compounds in decreasing order of Keq. for hydrate formation.
O O O
|| || ||
(1) C6H5COCH3 (2) Cl C - CH 3 (3) NO2 C - CH 3 (4) CH3 C - CH 3
Paragraph for Q. 05 to 06
Two reactions which are example of nucleophilic attack are given as below .
R1
pH = x
Reaction - I : C = O + HCN
R2
R1
pH = y
Reaction - II : C = O + NH2–C–NH–NH2
R2
O
Q.5 Value of x is :
(A) x < 4.5 (B) x = 6 (C) x > 7 (D) Can't decide
Q.6 Value of y is :
(A) x = 4.5 (B) x = 1.5 (C) x = 7 (D) x = 9
Q.7 Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give aldehydes.
Propose mechanisms for the two steps in this synthesis.
Q.8 A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest reagents
appropriate for each step in the synthesis.
O O OH
|| || |
58% 54%
(CH 3 )3 CCCH 3 ¾¾¾®(CH 3 )3 CCCH 2 Br ¾¾¾®(CH 3 )3 CCHCH 2 Br ¾68
¾¾ %
®(CH 3 )3
Q.9 Predict the organic products :
O
|| +
(i) H / D
(i) H + / D
(a) CH 3 - C - CH 3 + CH 3 - CH 2 - NH 2 ¾¾¾¾
(ii ) H 2 / Pt
® (b) ¾¾¾¾
(ii) H 2 / Pt
®
O
||
(c) C - CH 3 ¾¾¾¾¾¾
(i) Cl2 / NaOH / HOH
¾®z
Å
(ii) H
Paragraph for Q.No.10 to 11
A(Hydrocarbon) (C Þ 88.24%) [Molecular weight of A = 68]
(i) Na
A (ii) n-propyl bromide B (C8H14)
2+
Hg
A dil. H2SO 4
C5H6O (C)
KMnO 4
A + Carboxylic acid + Gas
H
Q.10 'A' can be :
(A) H3C–H 2C–CºC–CH3 (B) CH3–CH2–CH2–CºC–H
CH3
(C) CH3—CH—C CH (D)
CH3
Q.11 Correct statement reagarding C is.

(A) C reacts with fehling solution to give red ppt. (B) C gives +ve iodoform test
(C) C give –ve 2, 4, D.N.P test (D) C is aldehyde
–
HCHO, OH
Q.12 CH3CH2CH2 –CH–CH = O A(C7H14O2)
CH3 –
HCHO /OH
B (C7H16O2) (formed as one

of the product)
'B' is :
CH2OH CH2–OH
(A) CH3–CH2–CH2– CH–CH2 CH2 OH (B) CH3–CH2–CH2– C—CH 2OH
CH3
CH2–OH
(C) CH3–CH2CH2– C—CH 2OH (D) CH 3–COONa
CH3
Q.13 Identify A to E :
Br2 (1eq)
(Structural isomer)
Q.14 Show how you would accomplish the following syntheses efficiently and in good yield. You may
use any necessary reagents.
(a) ¾® (b) ¾®
(c) ¾® (d) ¾®
(e) ¾® (f) ¾®
Paragraph for Q.No. 15 to 16

Identify the lettered compounds in the following reaction shceme. Compounds F, G and K are
isomers of molecular formula C13H18O. How could 1H NMR spectroscopy distinguish these three
compounds from each other ?
(1) O3
O C
(2) CH3SCH3
(1) Mg
(1) C6H5MgBr H2SO4 HCl (2) CH2=O
A B D (3) H2O
F
(2) H2O
mCPBA (1) (CH3)2CuLi

E G
(1) LiAlH4 (2) H2O
(2) H2O
PBr3 Mg (1) C6H5CHO

H I J K
(2) H2O
Q.15 Identify 'K' product ?
Ph O COOH
HO–CH–Ph —Ph
HO Ph
Ph
(A) (B) (C) (D)
Q.16 Identify 'G' product ?

Ph OH OH
O Ph
O Ph Me Me
(A) (B) (C) (D)
Paragraph for Q.No. 17 to 18

In given reaction sequence
(i) O3
(A) (B) + (C)
(ii) Zn / H2O
C10H20 Racemic mixture
Optically of carbonyl compounds
inactive alkene
Br2
in CCl4 H2N–OH
(D) + (E) Oxime(s)

Mixture of two different
meso compounds
17. Alkene A is :
H H H H
(A) (B) (C) (D)
H H H H
18. How many total oxime(s) is/are obtained

(A) 1 (B) 2 (C) 3 (D) 4
EXERCISE # IV (MAINS)
Q.1 When CH2 = CH–COOH is reduced with LiAlH4, the compound obtained will be -
[AIEEE-2003]
(1) CH3–CH2–CH2OH (2) CH3–CH2–CHO
(3) CH3–CH2–COOH (4) CH2=CH–CH2OH
Q.2 Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the
corresponding alcohol and acid ? [AIEEE-2004]
(1) Phenol (2) Benzaldehyde (3) Butanal (4) Benzoic acid
Q.3 Which one of the following is reduced with Zn-Hg/HCl to give the corresponding hydrocarbon
[AIEEE-2004]
(1) Butan-2-one (2) Acetic acid (3) Acetamide (4) Ethyl acetate
Q.4 On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant solution is
[AIEEE-2004]
(1) CH3COOC2H5 + NaCl (2) CH3COONa + C2H5OH
(3) CH3COCl + C2H5OH + NaOH (4) CH3Cl + C2H5COONa
Q.5 The best reagent to convert pent–3–en–2–ol into pent –3–en –2–one is - [AIEEE-2005]
(1) Acidic dichromate (2) Acidic permanganate
(3) Pyridinium chloro-chromate (4) Chromic anhydride in glacial acetic acid
Q.6 Rate of the reaction- [AIEEE-2005]

O O –
R—C + Nu– R—C + X
X Nu
is fastest when X is -
(1) NH2 (2) Cl (3) OCOR (4) OC2H5
Q.7 Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is-
(1) CH3CH2CH(OH)CH2CH3 (2) C6H5CH2CH2OH [AIEEE-2006]
CH3
(3) H3C (4) PhCHOHCH3
OH
Q.8 In the following sequence of reactions

P + I2 Mg HCHO H2O
CH3CH2OH A
Ether
B C D, then compound 'D' is - [AIEEE-2007]
(1) Butanal (2) n–Butyl alcohol
(3) n–Propyl alcohol (4) Propanal
Q.9 In the following sequence of reactions, the alkene affords the compound ‘B’ :- [AIEEE-2008]
O3 HO
CH3CH = CHCH3 ¾¾¾ ® A ¾¾¾¾
Zn ® B.
2
The compound B is
(1) CH3CH2CHO (2) CH3COCH3 (3) CH3CH2COCH3 (4) CH3CHO
Q.10 Bakelite is obtained from phenol by reacting with [AIEEE-2008]

(1) (CH2OH)2 (2) CH3CHO (3) CH3COCH3 (4) HCHO
Q.11 Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(1) CH2ClCH2Cl (2) CH3CHCl2 (3) CH3COCl (4) CH3CH2Cl
Q.12 In Cannizzaro reaction given below :- [AIEEE-2009]

: OH
2PhCHO PhCH2OH + PhCO2–
the slowest step is :-
(1) The abstraction of proton from the carboxylic group
(2) The deprotonation of PhCH2OH
–
(3) The attack of : OH at the carboxyl group
(4) The transfer of hydride to the carbonyl group
Q.13 One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene is :- [AIEEE-2010]
(1) Ethene (2) Propene (3) 1-Butene (4) 2-Butene
Q.14 Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the
presence of :- [AIEEE-2011]
(1) An isopropyl group (2) An acetylenic triple bond
(3) Two ethylenic double bonds (4) A vinyl group
Q.15 Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar mixture.
Identify 'A' from the following compounds : - [AIEEE-2011]
(1) 2-Methyl - 1- pentene (2) 1-Pentene
(3) 2-Pentene (4) 2-Methyl-2-pentene
Q.16 Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the
products contains sodium trichloroacetate and another compound. The other compound is :-
[AIEEE-2011]
(1) 2,2,2–Trichloropropanol (2) Chloroform
(3) 2,2,2–Trichloroethanol (4) Trichloromethanol
Q.17 Silver Mirror test is given by which one of the following compounds? [AIEEE-2011]
(1) Formaldehyde (2) Benzophenone (3) Acetaldehyde (4) Acetone
Q.18 In the given transformation, which of the following is the most appropriate reagent ? [AIEEE-2012]
CH=CHCOCH3 CH=CHCH2CH3
¾¾¾¾
®
Re agent
HO HO
(1) NaBH4 (2) NH2 NH2, OH (3) Zn – Hg / HCl (4) Na, Liq.NH3
Q.19 Iodoform can be prepared from all except :- [AIEEE-2012]

(1) Isobutyl alcohol (2) Ethyl methyl ketone
(3) Isopropyl alcohol (4) 3-Methyl–2–butanone
Q.20 A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular
mass 390. The number of amino groups present per molecule of the former compound is :-
[JEE(Main)-2013]
(1) 2 (2) 5 (3) 4 (4) 6
Q.21 The major organic compound formed by the reaction of 1, 1, 1–trichloroethane with silver powder
is :- [JEE(Main)-2014]
(1) 2-Butyne (2) 2-Butene (3) Acetylen (4) Ethene
Q.22 The most suitable reagent for the conversion of R – CH2 – OH ® R – CHO is :-
[JEE(Main)-2014]
(1) CrO3 (2) PCC (Pyridinium chlorochromate)
(3) KMNO4 (4) K2Cr2O7
Q.23 A compound A with molecular formula C10H13Cl gives a white precipitate on adding silver nitrate
solution. A on reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis
gives C and D. C gives Cannizaro reaction but not aldol condensation. D gives aldol condensation
but not Cannizaro reaction. A is : [JEE(Main)-2015]
CH2–CH2–CH3
CH2–Cl
CH3
(1) (2) C6H5–CH 2–C
CH3
Cl
(3) C6H5–CH2–CH2–CH2–CH2–Cl (4) C6H 5–CH2–CH2–CH–CH3

Cl
Q.24 In the reaction sequence [JEE(Main)-2015]
-
2CH 3 CHO ¾¾¾
OH D
® A ¾¾ ® B ; the product B is:-
(1) CH3–CH=CH–CHO (2) CH3–CH2–CH2–CH3

O
(3) CH3–CH2–CH2–CH2–OH (4) CH3–C–CH3
Q.25 Which compound would give 5-keto-2-methyl hexanal upon ozonlysis? [JEE(Main) 2015]
CH3 CH3 CH3 CH3
H3C CH3
(1) (2) (3) (4)
CH3 CH 3
Q.26 The correct sequence of reagents for the following conversion will [JEE(Main) 2017]
be :
(1) CH 3MgBr, [Ag(NH3 )2 ]+OH−, H+/CH3OH
(2) [Ag(NH3 )2 ]+OH−, CH 3MgBr, H+/CH3 OH
(3) [Ag(NH3 )2 ]+OH−, H+/CH 3OH, CH3 MgBr
(4) CH3 MgBr, H+/CH 3OH, [Ag(NH3 )2 ]+OH−
Q.27 The major product formed in the following reaction is: [JEE MAIN-2019]
(1) (2)
OH O
(3) H C H
(4)
3
Q.28 In the following reaction [JEE MAIN-2019]
Aldehyde + alcohol H Cl
 Acetal
Aldehyde Alcohol
t
HCHO BuOH
CH3CHO MeOH
The best combinations is :
(1) CH3CHO and tBuOH (2) HCHO and tBuOH
(3) CH3CHO and MeOH (4) HCHO and MeOH
Q.29 cannot bee prepared by : [JEE MAIN-2019]
(1) PhCOCH3 + CH3CH2MggX (2) PhCOCH2CH3 + CH3MgX

(3) HCHO + PhCH(CH3)CH
H2MgX (4) CH3CH2COCH3 + PhMgX
Q.30 In the following reactions, products A and B are : [JEE MAIN-2019]

[A] H
3O


 [B]
(1) (2)
(3) (4)
Q.31 The increasing order of the reactivity of the following with LiAlH4 is : [[JJEE MAIN-2019]
(1) (A) < (B) < (C) < (D) (2) (A) < (B) < (D) < (C)
(3) (B) < (A) < (C) < (D) (4) (B) < (A) < (D) < (C)
Q.32 The aldehydes which will noot form Grignard product with one equivalent Grignard reagents
are: [JEE MAIN-2019]
(1) (B), (C) (2) (B), (C), (D) (3) (C), (D) (4) (B), (D)
Q.33 Major products of the followwing reaction are: [JEE MAIN-2019]
CHO
(i) 50% NaOH
+ HCHO (ii) H3O+
COO
OH
(1) CH3OH and (2) CH3OH and HCO2H
CH2OH CH2OH COOH

(3) HCOOH and (4) and
Q.34 But-2-ene on reaction with alkaline KMnO4 at elevated temperature followeed by acidification
will give: [JEE MAIN-2019]
(1) one molecule of CH3CHHOO and one molecule of CH3COOH
(2) 2 molecules of CH3CHO O
(3) 2 molecules of CH3COO OH
(4)
Q.35 An organic compound neithher reacts with neutral ferric chloride solution no
or with Fehling
solution. It however, reacts with Grignard reagent and gives positive iodofo
orm test. The
compound is : [JEE MAIN-2019]
(1) (2)
(3) (4)
Q.36 The major product of the folllowing reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)
Q.37 The major product obtainedd in the following reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)
Q.38 
In the following reaction carrbonyl compound + MeOH 
HCl
 acetal. Ratee of the reaction is
the highest for : [JEE MAIN-2019]
(1) Acetone as substrate andd methanol in excess
(2) Acetone as substrate andd methanol in stoichiometric amount
(3) Propanal as substrate andd methanol in excess
(4) Propanal as substrate andd methanol in stoichiometric amount.
EXERCISE-IV # (A) (OBJECTIVE QUESTIONS)
Q.1 The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
Q.2 The enolic form of acetone contains: [IIT 1990]

(A) 9 sigma bonds, 1 pi bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pair
(D) 9 sigma bonds, 2 pi bonds and 1 lone pair
Q.3 m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
Q.4 Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
Q.5 An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent
and does not react with metallic sodium. It could be: [IIT 1993]
(A) CH3CH2CHO (B) CH3COCH3 (C) CH2=CH–CH2OH (D)CH2=CH–O–CH3
Q.6 Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane [IIT 1995]
-
¾¾® Ph–CH2OH + PhCO -2 the slowest step is:
Q.7 In the Cannizzaro reaction given below, 2Ph–CHO ¾OH
(A) The attack of OH– at the carbonyl group

(B) The transfer of hydride to the carbonyl group
(C) The abstraction of proton from the carboxylic acid
(D) The deprotonation of Ph–CH2OH [IIT 1996]
Q.8 Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is :
[IIT 1997]
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe
Q.9 In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]
H H
| |
(A) C6 H 5 - C - O - (B) C6 H 5 - C - O - (C) (D)
| |
OH O-
Q.10 CH3CHO + H2NOH ¾® CH3 – CH = N – OH. The above reaction occurs at: [IIT 1997]
(A) pH = 1 (B) pH = 4.5
(C) Any value of pH (D) pH = 12
Q.11 Among the following compounds, which will react acetone to give a product containing > C = N–
(A) C6H5NH2 (B) (CH3)3N (C) C6H5NHC6H5 (D) C6H5NHNH2
[IIT 1998]
Q.12 The product obtained via oxymercuration (HgSO4–H2SO4) of 1-butyne would be [IIT 1998]
O
||
(A) CH 3CH 2 - C - CH 3 (B) CH3CH2CH2CHO
(C) CH3CH2CHO + HCHO (D) CH3CH2COOH + HCOOH
Q.13 Which of the following will undergo aldol condensation: [IIT 1998]
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
Q.14 Which of the following will react with water: [IIT 1998]
(A) CHCl3 (B) Cl3CCHO (C) CCl4 (D) ClCH2CH2Cl
Q.15 A new carbon-carbon bond formation is possible in [IIT 1998]

(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
Q.16 Which of the following has the most acidic hydrogen: [IIT 2000]
(A) 3-hexanone (B) 2,4-hexanedione
(C) 2,5-hexanedione (D) 2,3-hexandione
Q.17 A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol [IIT 2001]
Q.18 1-propanol & 2-propanol can be best distinguished by : [IIT 2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling solution
Q.19 Compound A (molecular formula C3H8O) is treated with acidified potassium dichromate to form a
product B (molecular formula C3H6O). B forms a shining silver mirror on warming with ammonical
silver nitrate. B when treated with an aqueous solution of H2NCONHNH2. HCl and sodium acetate
gives a product C. Identify the structure of C. [IIT 2002]
(A) CH3CH2CH = NNHCONH2 (B) CH3 - C = NNHCONH 2

|
CH3
(C) CH3 - C = NCONHNH2 (D) CH3CH2CH=NCONHNH2

|
CH3
°
( i ) NaOH ( excess ) 100 C
Q.20 ¾¾ ¾ ¾ ¾ ¾ ¾¾ ® [IIT 2003]
(ii ) H + / H 2O
any one of the products formed is :
(A) (B)
(C) (D)
Acidic
Q.21 ¾¾¾® Products formed by P & Q can be differentiated by: [IIT 2003]
Hydrolysis
(A) 2, 4 DNP (B) Lucas reagent (ZnCl2) conc. HCl

(C) NaHSO3 (D) Fehlings solution
Q.22 The order of reactivity of phenyl Magnesium Bromide with the following compounds is [IIT 2004]
(A) II > III > I (B) I > III > II (C) II > I > III (D) All react with the same rate
CH COONa
Q.23 + X ¾¾3¾ ¾¾® [IIT 2005]
What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO–COOH
Q.24 The smallest ketone and its next homologue are reacted with NH2OH to form oxime.
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active [IIT 2006]
Q.25 Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E.
Compound E on further treatment with aqueous KOH yields compound F. Compound F is
[IIT 2007]
(A) (B) (C) (D)
Q.26 Statement-1 : Glucose gives a reddish-brown precipitate with Fehling’s solution.

because
Statement-2 : Reaction of glucose with Fehling’s solution gives CuO and gluconic acid.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True. [IIT 2007]
Q.27 Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate your
answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS. [IIT 2007]
Column I Column II
(A) C6H 5CHO (P) gives precipitate with 2,4-dinitrophenylhydrazine
(B) CH 3CºCH (Q) gives precipitate with AgNO3
(C) CN – (R) is a nucleophile
(D) I– (S) is involved in cyanohydrin formation
Paragraph for Question No. 28 to 30

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to
compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound
L, whereas K on reaction with KOH gives only M.
O
H3 C
Ph
M=
Ph H
Q.28 Compound H is formed by the reaction of [IIT 2008]

O O
|| ||
(A) Ph CH3 + PhMgBr (B) Ph CH3 + PhCH2MgBr
O O Me
|| ||
(C) Ph H + PhCH2MgBr (D) Ph H + Ph MgBr
Q.29 The structure of compound I is [IIT 2008]

Ph CH3 H3C Ph Ph CH3 H3C CH3
(A) (B) (C) (D)
H Ph H Ph H CH2Ph Ph H
Q.30 The structures of compounds J, K and L, respectively, are [IIT 2008]

(A) PhCOCH3, PhCH2COCH3 and PhCH2COO¯K+
(B) PhCHO, PhCH2CHO and PhCOO¯K+
(C) PhCOCH3, PhCH2CHO and CH3COO¯K+
(D) PhCHO, PhCOCH3 and PhCOO¯K+
Paragraph for Question Nos. 31 to 33
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.
1. MeMgBr
P ¾¾+¾¾® Q ¾¾¾¾
1. O3
2. Zn,H 2 O
® R ¾¾¾
1. OH ¯
2. D
®S
2. H , H 2O
3. H 2SO 4 , D
Q.31 The structure of the carbonyl compound P is [IIT 2009]

O
Me
(A) (B) (C) (D)
O Me O Me O Et Me
Q.32 The structure of the products Q and R, respectively, are [IIT 2009]
O
(A) Me , H
COMe
Me
Me Me Me
O
(B) , H
CHO
Me
Me Me Me
O
(C) , H
CHO
Et
Me Me Et
Me O
CH3
(D) ,
CHO
Me Me Et
Q.33 The structure of the product S is [IIT 2009]
O O O
Me
(A) (B) (C) (D)
O
Me Me Me Me
Me
Paragraph for Questions Nos. 34 to 35
An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product
through the following sequence of reactions, in the which Q is an intermediate organic compound.
(i) conc.H2SO4
(Catalytic amount) O
(i) dil H2SO4/HgSO4 (–H2O)
P Q 2 C
(C6H10) (ii) NaBH4/ethanol (ii) O3 H3C CH3
(iii) dil.acid (iii) Zn/H2O
Q.34 The structure of compound P is - [IIT 2011]
(A) CH3CH2CH2CH 2–CºC–H (B) H3CH2CºC–CH2CH3
H3C H3C
(C) H–C–CºC–CH3 (D) H3C–C–CºC–H
H3C H3C
Q.35 The structure of the compound Q is - [IIT 2011]
H3C OH H3C OH
(A) H–C–C–CH2CH3 (B) H3C–C–C–CH3
H3C H H3C H
H3C OH OH
(C) H–C–CH2CHCH3 (D) CH3CH2CH2CHCH2CH3
H3C
Q.36 The number of aldol reaction(s) that occurs in the given transformation is [IIT 2012]
OH OH
conc. aq. NaOH
CH3CHO + 4HCHO
HO OH
(A) 1 (B) 2 (C) 3 (D) 4
Q.37 Among P, Q, R and S, the aromatic compound(s) is / are : [IIT 2013]

Cl
¾¾¾
AlCl3
® P ¾¾¾NaH
® Q
O
¾¾¾¾® R
(NH 4 )2 CO3
100 -115ºC ¾¾®
HCl S
OO
(A) P (B) Q (C) R (D) S
Q.38 After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is(are)
[IIT 2013]
O
CH3 ¾¾¾¾¾¾ ®
Br2 (1.0 mol)
Reaction I : H3C aqueous / tyh; NaOH
(1.0 mol)
O
CH3 ¾¾¾¾ ¾ ®
Br2 (1.0 mol)
Reaction II : H3C CH3 COOH
(1.0 mol)
O O O O O
H3C CH2Br H3C CBr3 Br3C CBr3 BrH 2C CH2Br H3C ONa CHBr3
P Q R S T U
(A) Reaction I : P and Reaction II : P
(B) Reaction I : U, acetone and Reaction II : Q acetone
(C) Reaction I : T, U, acetone and Reaction II : P
(D) Reaction I : R, acetone and Reaction II : S acetone
Q.39 The major product in the following reaction is [IIT 2014]

O
Cl 1. CH3MgBr, dry ether, 0ºC
CH3 2. aq. acid
O OH
(A)
H3C (B) H2C CH3
CH3 CH3
CH3
(C) (D)
O CH2 O CH3
Q.40 The major product of the following reaction is - [IIT 2015]

O
I. KOH, H2O
CH3
O II. H+, Heat
CH3 CH3
O
O O O CH3
CH3
(A) (B) (C) (D)
Q.41 In the following reactions, the product S is - [IIT 2015]
H3C
I. O3 NH3
R S
II. Zn,H2O
H3C H3C N
N
(A) (B)
N
N
(C) (D)
H3C H3C
Q.42 Positive Tollen's test is observed for : [IIT 2016]
H O CHO
(A) (B)
H
H
H
OH O
Ph
(C) Ph (D) Ph Ph
O
Q.43 The major product of the following reaction sequence is : [IIT 2016]
O
(i) HCHO (excess) / NaOH, heat

+
(ii) HCHO / H (catalytic amount)
O O O O OH
(A) (B)
O O O OH
HO
(C) (D)
OH
Q.44 Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q and S is
C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, where S undergoes haloform reaction
but not Cannizzaro reaction. [IIT JEE 2017]
i )O3 / CH 2 Cl 2
(i) P 
ii) Zn/ H 2 O
 Q
(C8H8O)
i )O3 / CH 2 Cl 2
(ii) R 
ii) Zn/ H 2 O

S
(C8H8O)
The option(s) with suitable combination of P and R, respectively, is (are)
H 3C
CH3 CH3
H3 C and and
(A) (B) CH3
CH3
H3 C
H3 C CH3
CH3 CH3
and H3C H3C
(C) (D) and
CH3 CH3
CH3
Q.45 The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [IIT JEE 2018]
(A) (B)
(C) (D)
Q.46 The desired product X can be prepared by reacting the major product of the reactions in
LIST-I with one or more appropriate reagents in LIST-II.
(given, order of migratory aptitude: aryl > alkyl > hydrogen) [IIT JEE 2018]
List-I List-II
P. + H2SO4 1. I2, NaOH
Q. + HNO2 2. [Ag(NH3)2]OH
R. + H2SO4 3. Fehling solution
S. + AgNO3 4. HCHO, NaOH
5. NaOBr
The correct option is
(A) P  1; Q  2,3; R  1,4; S  2,4 (B) P  1,5; Q  3,4; R  4,5; S  3
(C) P  1,5; Q  3,4; R  5; S  2,4 (D) P  1,5; Q  2,3; R 1,5; S  2,3
Q.47 Choose the correct option(s) for the following set of reactions [IIT JEE 2019]
i) MeMgBr conc. HCl
C6H10O ii) H2O
Q S
(major)
20% H3PO4, 360 K
T i) H2, Ni R HBr, benzoyl peroxide U

ii) Br2, hv 
(major) (major) (major)
CH3 H3C Br H3C Cl CH3

Br Br
(A) (B)
U T S U
CH3 H3C Br H3C Br CH3
Cl Cl
(C) (D)
S T U S
EXERCISE-IV # (B) (SUBJECTIVE QUESTIONS)
NaOC H in absolute
Q.1 C6H5–CHO + CH3 – COOC2H5 ¾¾ ¾2¾5 ¾ ¾¾® (D). [IIT 1995]
C 2H 5OH and heat
( i ) KCN / H SO
Q.2 C = O ¾¾ ¾ ¾ ¾
2
¾4 ® D. [IIT 1996]
(ii ) LiAlH 4
Q.3 Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes.
Write structures of the oximes. [IIT 1997]
Q.4 An aldehyde (A) (C11H8O), which does not undergo self aldol condensation, gives benzaldehyde
and two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid.
Identify the compounds (A) and (B). [IIT 1998]
( i ) LiAlH
Q.5 ¾(¾
C)
® ¾¾ ¾ ¾4 ® (D) [IIT 1998]
( ii ) H + , heat
Q.6 What would be the major product in each of the following reaction? [IIT 2000]
¾Base
¾¾®
Q.7 Identify (A), (B) and (C), and give their structures. [IIT 2000]
¾¾Br2
NaOH
® A + B
C (C7H12O)
Q.8 Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification. Based on the following observations, give structure of the compounds.
(i) Both A and B form a silver mirror with Tollen's reagent; also, B gives a positive test
with FeCl3 solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene. [IIT 2002]
Q.9 C6H12 ¾HCl
¾¾® C6H13Cl + (C)
(A) (B)
ozonolysis
(D) ¾¾ ¾¾® (E)
(A) ¾ozonolysis
¾ ¾¾® (F) + (G) ¾NaOH
¾¾® HCOONa + 1° alcohol
(D) is isomer of A. E gives negative test with Fehling solution but gives iodoform test F and G gives
Tollen's test but do not give iodoform test. Identify A to G. [IIT 2003]
Answer Key
EXERCISE # I
1 (A) 2 (B) 3 (C) 4 (D) 5 (C)
6 (B) 7 (C) 8 (C) 9 (D) 10 (C)
11 (A) 12 (C) 13 (C) 14 (C) 15 (C)
16 (D) 17 (A) 18 (C) 19 (D) 20 (C)
21 (C) 22 (B) 23 (D) 24 (B) 25 (C)
26 (D) 27 (B) 28 (A) 29 (B) 30 (C)
31 (D) 32 (D) 33 (B) 34 (C) 35 (C)
36 (D) 37 (B) 38 (C) 39 (B) 40 (A)
41 (D) 42 (C) 43 (D) 44 (B) 45 (B)
46 (C) 47 (A) 48 (C) 49 (C) 50 (D)
EXERCISE # II
1 (A,B) 2 (C,D) 3 (A,B,C) 4 (A,B,C) 5 (B,C)
6 (A,B) 7 (A,B,C,D) 8 (A,B,C) 9 (A,C,D) 10 (B,C,D)
11 (A,D) 12 (D) 13 (C) 14 (C) 15 (D)
16 (B) 17 (B) 18 (C) 19 (B) 20 (B)
21 (A,B,C)
22 (A)P, (B)Q, (C)S, (D)R
23 (A) R, (B) Q,S, (C) S, (D) P
EXERCISE # III
Q.1
OH OH
| |
Ans. (a)
CH - CH
3 - CH 2 - CH 3
(b) CH 3 - CH 2 - CH - C º CH
OH
|
(c) CH 3 - CH 2 - CH - Ph (d) CH 3 - CH 2 - CH - OCH3
|
OCH3
(e) CH3 – CH2 – CH (f) CH3–CH2–CH=NH–Ph
OH
|
(g) CH 3 - CH 2 - CH - N - CH 3 (h) CH3–CH2–CH=N–OH
|
CH 3
(i) CH3–CH2–CH=N–NH 2 (j) CH3–CH2–CH2
(k) p-Nitro phenyl hydrazon (l) Semi carbazone
OH
|
(m) CH 3 - CH 2 - CH - CN (n) CH3–CH2–CO2H
Q.2
O
||
Ans. (a) C - C - C - C - OH (b) CH3 - CH2 - CH 2 - CH = C - CH 2 - CH3 (c) C–C–C–C=N–OH
|
CHO
OH OH
| |
(d) C - C - C - C - Ph (e) Ph - CH = C - CH 2 - CH 3 (f) C - C - C - CH - C º CH
|
CHO
(g) C–C–C–C (h) C–C–C–C (i) 2°alcohol (j) Cyanohydrine (k) 1° alcohol
OH
|
(l) CH 3 - CH 2 - CH 2 - CH - CH - CO 2H
|
Et
Q.3 Ans. (A) P,Q,S ; (B) P,Q,S ; (C) P,Q,S ; (D) P,Q,S
Q.4 Ans. 3 > 2 > 1 > 4 Q.5 Ans. (C) Q.6 Ans. (A)
Q.7
O - CH 2 CH 3 O - CH 2 CH 3 O
| | ||
+
Ans. H - C - O - CH 2CH 3 + R – Mg – X ¾® R - C - O - CH CH ¾H¾3O
¾ ® R - C -H
| 2 3
|
O - CH 2CH 3 H
Ethyl orthoformate Acetal
aldehyde
Q.8
Ans. H+/Br2 ; H2 / Ni ; NaOH
Q.9 O
||
Ans. (a) CH 3 - CH - NH - CH 2 - CH 3 (b) (c) CHCl3 + C - OH
|
CH 3
Q.10 Ans. (B,C) Q.11 Ans. (B) Q.12 Ans. (B)
Q.13 Ans. Not available
Q.14
Ans. (a) (i) KMnO4, (ii) CH 2 - OH , (iii) LiAlH4, (iv) H3OÅ
|
CH 2 - OH
(b) (i) CH 2 - OH , (ii) NaBH4, (iii) H3O+, (c) (i) CH 2 - OH , (ii) Ph3P=CH–Et
| |
CH 2 - OH CH 2 - OH
(d) (i) H2, Ni (e) NH2NH2/H2O2 (f) NaBH4
Q.15 Ans. (A) Q.16 Ans. (D) 17. Ans. (B) 18. Ans. (D)
EXERCISE # IV (MAINS)
1. (4) 2. (2) 3. (1) 4. (2) 5. (4)
6. (2) 7. (4) 8. (3) 9. (4) 10. (4)
11. (2) 12 . (4) 13. (4) 14. (4) 15. (4)
16. (3) 17. (1 , 3) 18. (2) 19. (1) 20. (2)
21. (1) 22. (2) 23. (2) 24. (1) 25. (4)
26. (3) 27. (2) 28. (4) 29. (3) 30. (1)
31. (2) 32. (4) 33. (3) 34. (3) 35. (1)
36. (3) 37. (3) 38. (3)
EXERCISE # IV - A (OBJECTIVE QUESTIONS)
1 (B) 2 (A) 3 (D) 4 (B) 5 (D)

6 (D) 7 (B) 8 (A) 9 (D) 10 (B)
11 (A,D) 12 (A) 13 (A,B,D) 14 (B) 15 (B,D)
16 (B) 17 (A) 18 (C) 19 (A) 20 (C)
21 (D) 22 (C) 23 (C) 24 (B) 25 (A)
26 (C) 27 (A) P,S; (B) Q; (C) Q,R,S; (D) Q,R 28 (B)
29 (A) 30 (D)
31 (B) 32 (A) 33 (B) 34 (D) 35 (B)
36 (C) 37 (A,B,C,D) 38 (C) 39 (D) 40 (A)
41 (A) 42 (A,B,C) 43 (A) 44 (A, B) 45 (A, B,D)
46 (D) 47 (A,B)
EXERCISE - IV # B (SUBJECTIVE QUESTIONS)
Q.1
Ans. C6H5CH = CHCOOC2H5 , CH3 – CH = CH – COOC2H5
Q.2
Ans. C
(D)
(A racemic mixture)
Q.3
Ans. C 6 H 5 - C - CH 3 and C 6 H 5 - C - CH 3
|| ||
N - OH HO - N
syn anti(isomers )
Q.4
CHO +
Ans. Ozonolysis
¾¾ ¾ ¾
¾® + 2| ¾Ag
¾¾® COOH
COOH |
COOH
(B)
(Oxalic acid)
Q.5 Q.6
Ans. ¾¾
C H CHO
¾ ¾®
6 5
Ans. ¾Base
¾¾®
+ Base
(C) (D)
Q.7
Ans. Br + NaOH + CHBr3

¾¾2 ¾ ¾
¾®
(A) (B) (C)
Q.8
Ans. (A) or (B) (C) (D) (E)
Q.9
Ans. Me3C – CH=CH2 ¾HCl
¾¾® Me2 C –CHMe2 + Me3C– CH –Me
| |
Cl Cl
(A) (B) (C)
Alc. KOH
Ozonolysis
2 O
NaOH
(A) ¾Ozonolysis
¾ ¾¾ ¾® HCHO + Me3C–CHO ¾¾¾® S
(F) (G)
HCOONa + Me3C–CH2OH (1° Alcohol)
2019
100 Percentile 99.99 Percentile 99.98 Percentile 99.98 Percentile 99.97 Percentile 99.97 Percentile 99.96 Percentile 99.96 Percentile
HIMANSHU GAURAV SINGH GAURAV KRISHAN GUPTA SARTHAK ROUT VIBHAV AGGARWAL RITVIK GUPTA BHAVYA JAIN AYUSH PATTNAIK SAYANTAN DHAR
2019 (*SDCCP) 2020 (DLP) 2020 (CCP) 2019 (CCP) 2020 (DLP) 2020 (CCP) 2019 (CCP) 2020 (DLP)
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Carbonyl Compound

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ENTHUSE

AIR-1 AIR-3 AIR-6 AIR-8

JEE MAIN RESULTS 2020 (January Attempt) OF NUCLEUS EDUCATION

JEE ADVANCED RESULTS OF NUCLEUS EDUCATION

AIR-10 AIR-12 AIR-23 AIR-24 AIR-37 AIR-42 AIR-66 AIR-98

AIR-20 AIR-27 AIR-32 AIR-61 AIR-67 AIR-78 AIR-61 AIR-91

AIR-2 AIR-19 AIR-33 AIR-48 AIR-51 AIR-53 AIR-86

Q.2 In the given reaction

Q.3 In the given reaction:

Q.4 In the reaction :

Q.8 Gem dihalide on hydrolysis gives :

Q.10 In the given reaction :

(C) Br–CH2–COOC2H5 (D) CH–COOC2H5

Q.11 Cross cannizzaro reaction is example of :

(A) KOH (B) KOH followed by LAH

Q.15 In the given reaction :

Q.16 In the reaction sequence :

Q.18 The given reaction :

Q.19 The product of the reaction :

O2N CHO + (C6H5–CH2CO)2O

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

Q.20 Cyanohydrin of which compound on hydrolysis will give lactic acid ?

Q.21 In the given reaction :

(A) CH2 OH and HO CH2 O

(B) CH3 O and HO CH2 O

(C) CH2 OH and CH3 OH

(D) CH2 OH and O

Q.22 Acetaldehyde cannot give :

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

Q.24 The reaction in which NaCN/C2H5OH/HOH is used is :

(A) Perkin reaction (B) Benzoin condensation

Compound A contains how many hydroxy groups ?

(A) 1 (B) 2 (C) 3 (D) 4

(Y) will be: 

(D) HCHO and C6H5CHO

Identify relationship between A & B products ?

Q.29 In the reaction sequence

the product (B) is :

the product (A) is :

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

Q.32 The conversion

can be effected by using the reagent

Q.33 In the reaction

the major product is :

Q.35 The major product obtained in the reaction is

Q.36 Total number of stereoisomers of major product (Q) are :

(A) 0 (B) 4 (C) 8 (D) 2

Q.37 CH3CHO + NH2OH ® CH3CH = N—OH

Q.39 The compound having the highest dipole moment is :

Question No. 41 to 43 (3 questions)

Q.41 Which is not correct about (A) ?

Q.43 Which is not correct about C?

Question No.44 to 48 (5 questions)

Q.44 Structutre of 'A' would be

Q.45 Structure of B would be

Q.46 'X' should be

(Question No. 49 & 50)

Q.49 Assertion : Benzaldehyde with HCN gives two isomeric compounds

Reason : There are no a–H in this compound, so it can't give aldol.

Q.3 Consider the structure of given alcohol:

Q.4 Correct option(s) regarding following reaction sequence is/are :

In above reaction (A) and (B) will respectively be

(A) & CH3CHO (B) CH3CH2Cl &