Carbonyl Compound Worksheet

EXERCISE-1
Q.1 Gem dihalide on hydrolysis gives :

(A)Vic diol (B) Gem diol
(C) Crbonyl compound (D) Carboxlic acid
Q.2 In the given reaction :
(a) and (b) respectively be :

(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
R
(C) (C6H5COO)2Ca and (CH3 COO)2Ca (D) (C6H5COO)2 Ca 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
(C) III > II > I > IV
Q.5 Acetal or ketal is

(A) Vic dialkoxy compound
(C) a- alkoxy alcohol
Q.6 In the given reaction

SI
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I
(D) I > IV > II > III
(B) a, w-dialkoxy compound

(D) Gem dialkoxy compound
J.
[X] will be-
(A) HCHO (B)
(C) (D) HCN
[X] will be-

N.
(A) only synoxime (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
Q.9 Schiff's reagent is used for the differentiation between :

(A) HCHO and CH3CHO
(B) CH3COCH3 and CH3CHO
(C)
(D) HCHO and C6H5CHO
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Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
Q.10 In the reaction sequence, [X] is ketone :
[X]
[X] will be
(A) (B) (C) (D)
Q.11 Which one of the following compounds will give dimetnyl glyoxal with SeO2:
(A) Acetone (B) Acetophenone
(C) Ethyl methyl ketone (D) Propanaldehyde

O
CH3
SeO2 [X]
R
[X] will be –
O
O O CH3
CHO
(A)
(C)
O
O
CH3
Q.13 Consider the given reaction:

SI (B)
(D)
O
CH3
O
J.
O O
C6H5COOH
CH3 – C – CH3 CH3 – C – O – CH3
The above reaction is known as-
(A) Baeyer-villiger oxidation (B) Oppenaur oxidation
(C) Periodate oxidation (D) Peroxide oxidation
N.
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 deceasing order :

O O O
(I) CH3 –C – CH2 – C – CH3 (II) CH3 – C – CH3

(III) CH  CH (IV) CH3– CHO
Select correct answer from the codes given below :
Codes-
(A) I > IV > III > II (B) I > IV > II > III
(C) III > I > IV > II (D) II > IV > I > III
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Mob. No. : 9214233360
CH3
NaOH
X+Y CH3 –CH – CH – CHO
5°C
CH3
(X) and (Y) will respectively be :
(A) CH3 – CH2 – CHO and CH3 – CH2– CHO
(B) CH3 – CHO and CH3 – CH2 – CHO
(C) CH3 – CHO and CH3 – CHO
CH3
(D) CH3 – CHO and CH3 –CHO and CH3 – C – CHO

CH3
R
Q.17 Number of products in the given reaction:

OH
C6H5CHO + CH3– CHO   Product will be
(A) one (B) Three (C) Two (D) Four
Q.18 In the reaction :
[X] will be-
(A)
OH O
O+
SI 
O OH/
(B)
[X]
OH OH
J.
O O
OH
(C) (D)
Q.19 Product of Perkin reaction is:

N.
(A) , - unsaturated aldehyde (B) -cyclohexyl ,-unsaturated aldehyde

(C) - Aryl-, - unsaturated acid (D) All of these
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Mob. No. : 9214233360
EXERCISE-2
Q.1 Which one of the following is mixed ketone:

O O
(A) CH3 – C –CH3 (B) CH3 – CH2 –C –CH3
O O
(C) Ph – C –CH3 (D) CH3 – C6H4 – C –CH2Ph
Q.2 In which of the following reactions product will be aldehyde?

(A) CH3 – C = C – C2H5 (i) O3 CO / H2 / CO2 ( CO )8
(B) CH3 –CH = CH2      
R
(ii) H2O 
CH3 CH3
B 2H6 HOH / HgSO 4 / H2SO 4
(C) CH3 – C  CH   (D) CH3 – C  CH       
NaOH , H2O 2
Q.3
Q.4
Q.5
(C) Isopropyl alcohol
SI
Which one of the following alcohols can be oxidised by K2CrO4?
(A) Ethanol (B) Tert butyl alcohol
(D) Allyl alcohol
Two isomeric ketones, 3-pentanone and 2- pentanone can be distinguished by:

(A) I2/ NaOH (B) NaSO3H (C) NaCN/HCl
Consider the structure of given alcohol:

OH
(D) 2,4-DNP
J.
C6H5 – C – CH3
C2H5
This alcohol can be prepared from:

O
(A) C6H5 – C –CH3 and C2H5MgBr

N.
(B) CH3 – CH2 –C –CH3 and C6H5MgBr

O
(C) C6H5 – C – C2H5 and CH3MgBr

O
(D) C6H5 – C –Cl and C2H5MgCl
Q.6 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
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Mob. No. : 9214233360
Q.7 In the reaction sequence :

NH2OH/H PCl5
C6H5 – C –CH3 [X]  [Y]
O
[Y] will be:
O O
(A) C6H5 – C –NHCH3 (B) CH3 – C –NH–C6H5

O
(C) C6H5 – CH2 –C –NH2 (D) C6H5CH2CN
Q.8 Fehling solution gives red precipitate with:
R
(A) Aromatic aldehyde (B) Aliphatic aldehyde
(C) Ketones (D) - hydroxy ketones
Q.9 Silver mirror test with Tollen's reagent is given by:

(A) C6H5CHO
(B) Ph – NH – OH
(C) C6H5 – CH2 –C– CH2OH
(D) CH3CHO
(A) Acetaldehyde
(C) Pivaldehyde
O
SI
Q.10 Which one of the following compounds will not give aldol:
Q.11 Knoevengel rection is catalysed by:

(B) Formaldehyde
(D) Crotonaldehyde
J.
(A) NaOH (B) NH3
(C) EtOk (D) Pyridine
Q.12 Which one of the following reagent(s) is/are used for the conversion of ketone into
hydrocarbons?
(A) LAH (B) N2H4/H2O 2 (C) Mg/Hg H2O (D) Na/Hg HCl
N.
Q.13 Schiff's reagent gives pink colour with:

(A) Acetaldehyde (B) Formic acid
(C) Acetic acid (D) Methyl acetate
Q.14 Which of the following compound will give positive Tollen's test
(A) CH3CHO (B)
O OH
OCH3
(C) CH3CH2CH2CH2CH – OCH3 (D) CH3–CH
OH OCH3
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Mob. No. : 9214233360
(i) Ph3P
Q.15 (A) CH– CH3
(ii) BuLi
(iii) (B)
In above reaction (A) and (B) will respectively be
(A) Cl & CH3CHO (B) CH3CH2Cl & O
Cl
(C) & HCHO (D) Cl & CH3CHO
CH3
Q.16 Which of the following form stable hemiketal:

O O
R
(A) Ph – C – Ph (B) HO – (CH2)3 – C – CH3
O O
(C) CH2OH –C – (CHOH)3 –CH2 – OH (D) HO –CH2 – (CH2)4 – C –CH3
(A)
(B)
CH2 = CH – C – H
CH2 = CH – C – H
O
SI
Q.17 Which of the following is example of 1,4-addition reaction
O
(i) NaCN
(ii) H2O
LAH
H2O/H
J.
CH3ONa/CH3OH
+CH2(COOMe)2
H3O
(C) O
O O
CH2= CH–CN
CH2–CH–CN
N.
Base
(D)
Q.18 Which of the following can be used for protection of carbonyl group:
(A) CH2OH – CH2OH/H (B) CH2OH –CH2 – CH2OH/ H
(C) HS – (CH2)3 – SH (D) CH2OH – CH2 – CHO
Q.19 Mixture of Ph – CHO and 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.20 Acetone give addition elimination reaction with

(A) Hydroxyl amine (B) Sodiumbisulphite
(C) Hydrogen sulphide (D) Ylide
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Mob. No. : 9214233360
Q.21 Which of the following will be soluble in sodium bicarbonate solution?
OH COOH
O2N NO2
(A) (B)
OH SO3H
NO2
(C) (D)
Q.22 Asparmate, an artificial sweetener is a peptide and has the following structure. Which of the
following is correct about the molecule?
O
R
C6H5
OH O
H2N NH
O
CH3
SI
(A) It has four functional groups
(B) It has three functional groups
(C) on hydrolysis it produces only one amino acid
(D) on hydrolysis it produces a mixture of amino acids
Q.23 Match List-I with List-II and select the correct answer using the codes given below the lists:
List-I (Compound) List- II (Used as)

J.
O
(A) 1,4 addition (P) Ph – CH2 – C – CH = CH2
(B) Tautomerism (Q) PCC
O
(C) Allylic bromination (R)

N.
O
(D) Preparation of Ketone from 2° alcohol (S) NBS
Q.24 Match list-I with list-II and select the correct answer using the codes given below the lists :
List-I List-II
NaBH4
(A) CH2 = CH – CHO   (P) Acetal

H
(B) C6H5CHO + Ph – NH2 
 (Q) Schiff's base
H
(C) C6H5COCH3 + CH3 – CH2 – NH2 
 (R) Unsaturated alcohol

H
(D) RCHO + 2RCH2OH 
 (S) Enamine
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Mob. No. : 9214233360
Q.25 Match list-I with list-II and select the correct answer using the codes given below the lists:
List-I List- II
OH  
(A) C6H5CHO + HCHO   C6H5CH2OH + HCOO (P) Cannizzaro reaction
Anhy.AlCl3
(B)C6H5 – H + CH3COCl    C6H5 –CO –CH3 (Q) Friedel Crafts reaction
Anhy .ZnCl 2
(C) C6H6 + CO + HCl     C6H5 –CHO (R) Reimer-Tiemann reaction
Cu2Cl 2
OH OH
(D) (i) CHCl3/Alc. KOH/ CHO (S) Gattermann- Koch

(ii) H
aldehyde synthesis
R
EXERCISE-3
Q.1 Predict the product of the reaction of propanal with each of the following:
(a) Lithium aluminium hydride
(b) Sodium borohydride
(c) Hydrogen (nickel catalyst)
SI
(d) Methylmagnesium iodide, followed by dilute acid
(e) Sodium acetylide, followed by dilute acid
(f) Phenyllithium, followed by dilute acid
(g) Methanol containing dissolved hydrogen chloride
(h) Ethylene glycol, p-toluene sulfonic acid, benzene
(i) Aniline (C6H5NH2)
(j) Dimethylamine, p-toluen sulfphonic acid, benzene
(k) Hydroxylamine
(l) Hydrazine
J.
(m)Product of part(I) heated in triethylene glycol with sodium hydroxide
(n) p- Nitrophenylhydrazine
(o) Semicarbazide
 ••
(p) Ethylidenetriphenylphosphorane [(C6H5)3 P – CHCH3 ]
(q) Sodium cyanide with addition of sulphuric acid
(r) Chromic acid
N.
Q.2 Give structure for the products of the reaction when butanal is treated with each of the
following reagents
 
 
(a) Ag (NH3)OH then HOH/H (b) OH/HOH, 

(c) NH2OH/H (d) C6H5Li then HOH

(e) C6H5CHO,OH,  (f) CH  CNa then HOH/H
(g) CH2OH–CH2OH, H
(h) SH–CH2 –CH2 –CH2 –SH then Raney Ni/H2
(i) CH3MgBr then H2O (j) HCN
(k) NaBH4
Br
(l) CH3–CH2 –CH –COOC2H5 and Zn then H2O/H 
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Mob. No. : 9214233360
Q.3 (a) Arrange the following compounds in decreasing order of Keq. for hydrate formation.
O
(1) C6H5COCH3 (2) Cl C –CH3
O O
(3) NO2 C –CH3 (4) CH3 C –CH3
(b) Equilibrium constants for the dissociation (Kdiss) of cyanohydrins according to the
equation
OH O
R
Kdiss
RCR RCR + HCN
CN
Cyanohydrin Aldehyde or Hydrogen
ketone cyanide
Q.4
OH
(i) CH3CH2CHCN or (CH3)2CCN
SI
have been measured for a number of cyanohydrins. Which cyanohydrin in each of the
following pairs has the greater dissociation constant?
OH
(ii) C6H5CHCN
OH
or
CH3
OH
C6H5CCN
Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give
aldehydes. Propose mechanisms for the two steps in this synsthesis.
J.
O–CH2CH3 O–CH2CH3 O
+
H3O
H –C –O –CH2CH3 + R – Mg – X R – C – O – CH2CH3 R–C–H
O–CH2CH3 H
ethyl orthoformate acetal aldehyde

N.
Q.5 Suggest a reasonable mechanism for each of the following reactions:

O
(CH3)3C O
NaOCH3
C CH2 CH OH (CH3)3CCCH2OCH3
3
Cl (88%)
Q.6 Predict the organic products:
O
H2/Pt
(a) CH3– C– CH3 + HO –CH2 – CH2 –NH2
CH2 – CH2 –CH2 – NH2 O
H2/Pt
(b) (c) (i) Cl2/ NaOH/HOH
– C –CH3 
O (ii) H
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Mob. No. : 9214233360
Q.7 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 O
58% 54% 68%
(CH3)3CCCH3 (CH3)3CCCH2Br (CH3)3CCHCH2Br (CH3)3CC – CH2
H
Q.8 Show how you would accomplish the following synthesis efficiently and in good yield. You
may use any necessary reagents.
O O
(a)
R
CHO CH2OH
O OH
(b)
(c)
O
CHO
CHO
O
SI CHO
CHCH2CH3
CHO
OH
J.
(d) H
O O
(e)
N.
O OH
(f) H
Q.9 Outline reasonable mechanisms for each of the following reactions:

O O
CH2CH2CH2CH2Br
KOC(CH3)3
benzene
(76%)
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Mob. No. : 9214233360
Q.10 Give the structure of the substance for each of the following reaction:
O
O C–CH3
NaOH/ NaOH/ NaOH/

(a) (X) (b) (Y) (c) (Z)
CH3 O
Q.11 Each of the following reactions has been reported in the chemical literature. Write the
structure of the product(s) formed in each case.
O
C6H5CH2SH
(a) H3C CH2
NaOH, H2O
R
O
O C6H5
KOH
Cl CH + C6H5
ethanol
(b)
Q.12 Identify A to E:
CH3
(i)
SH
SH
(ii) H2/Pt
O
NaOH
Br2(1er)
(i) CH3MgBr
(D)
SI
(A) + (B)
Conc.H2SO4/
(E)
J.
(ii) H2O/H
(C)
Q.13 Identify A to E in the given sequence of reaction:
O
SeO2/CH2Cl2 CF3COOOH H2O NH3/ (i) BH3/THF
(A) (B) (C) (D) (E)
(ii) H2O/H
N.
Q.14 Synthesis of each of the following compounds have been reported in the chemical literature.
Using the indicated starting material and any necessary organic or inorganic reagents,
describe short sequence of reactions that would be appropriate for each transformation.
(a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanone
O
C6H5
(b) from C6H5C
H3 C
CH2
CH3
(c) CCH2CH2CH2CH=CH2 from o-bromotoluene and 5-hexenal.
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Mob. No. : 9214233360
EXERCISE-4 (A)
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:

(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde [IIT 1991]
R
(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:
Q.5
Q.6
(A) Benzyl alcohol
(C) Benzoic acid
SI (B) Benzaldehyde
(D) Phenol
[IIT 1992]
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
(C) CH2= CH–CH2OH
(B) CH3COCH3
(D) CH2= CH –O –CH3
Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
J.
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol
(B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol
(D) Benzophenone into Diphenylmethane
Q.7 In the reaction, P is [IIT 1995]

N.
CH3
SeO2
CO P + Se + H2O
CH3
(A) CH3COCHO (B) CH3COOCH3
(C) CH3COCH2OH (D) None
OH – –
Q.8 In the Cannizzaro reaction given below, 2Ph –CHO   Ph –CH2OH + PhCO2 the
slowest step is :
(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]
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Mob. No. : 9214233360
Q.9 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.10 In a Cannizzaro reaction the intermediate which is the best hydride donor is:
[IIT 1997]
H H
– –
(A) C6H5 – C – O (B) C6H5 – C – O
OH O–
H H
R
–
O O–
(C) O– (D) O–
O2N CH3O
Q.11
Q.12
(C) Any value of pH
SI
CH3CHO + H2NOH  CH3 – CH = N – OH. The above reaction occurs at :
(A) pH = 1 (B) pH = 4.5
(D) pH = 12
[IIT 1997]
Among the following compounds, which will react acetone to give a product containing > C
=N–
(A) C6H5NH2
(C) C6H5NHC6H5
(B) (CH3)3N
(D) C6H5NHNH2
[IIT 1998]
J.
Q.13 The product obtained via oxymercuration (HgSO4 – H2SO 4) of 1- butyne would be
O
(A) CH3CH2 –C –CH3 (B) CH3CH2CH2CHO [IIT 1998]
(C) CH3CH2CHO + HCHO (D) CH3CH2COOH + HCOOH
N.
Q.14 Which of the following will undergo aldol condensation: [IIT 1998]
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
Q.15 Which of the following will react with water: [IIT 1998]
(A) CHCl3 (B) Cl3CCHO
(C) CCl4 (D) ClCH2CH2Cl
Q.16 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.17 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
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Mob. No. : 9214233360
Q.18 The appropriate reagent for the following transformation: [IIT 2000]
O
CH2CH3
CH3
HO HO
(A) Zn (Hg), HCl (B) NH2NH2, OH–

(C) H2/Ni (D) NaBH4
Q.19 A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution
gives: [IIT 2001]
(A) benzyl alcohol and sodium formate
(B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate
R
(D) benzyl alcohol and methyl alcohol
Q.20 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
Q.21
2002]
(A) CH3CH2CH= NNHCONH2
(C) CH3 – C = NCONHNH2
CH3
SI
and sodium acetate gives a product C. Identify the structure of C.
(B) CH3 – C = NNHCONH2
1- propanol and 2- propanol can be best distinguished by:

CH3
(D) CH3CH2CH= NCONHNH2
[JEE 2001]
[IIT
J.
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acedic 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
CHO OHC
N.
Q.22 (i) NaOH (excess) 100°C

[IIT 2003]
+
(ii) H /H2O
CHO OHC
any one of the products formed is:

CH2OH
COOH HOOC CH2OH
(A) (B)
COOH HOOC CH2OH
CH2OH
CH2OH COOH O
O
(C) (D)
COOH CH2OH
O
O
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Mob. No. : 9214233360
OCOCH3
P Acidic
Q.23    Products formed by P & Q can be differentiated by :
OCOCH3 Hydrolysis
Q
[IIT 2003]
(A) 2,4 DNP (B) Lucas reagent (ZnCl2) conc. HCl
(C) NaHSO3 (D) Fehlings solution
Q.24 The order of reactivity of phenyl Magnesium Bromide with the following compounds is :
[IIT 2004]
O O O
H3C CH3 H3C Ph

H Ph
R
(I) (II) (III)
(A) II > III > I (B) I > III > II

(C) II > I > III (D) All react with the same rate
Q.25
Q.26
MeO
What is X?
(A) CH3COOH
CHO
+ X 
SI
CH3COONa
 
(B) BrCH2, COOH

MeO
(C) (CH3CO)2O
COOH
[IIT 2005]
(D) CHO –COOH
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
J.
(C) Two oximes are optically active (D) All oximes are optically active
[JEE 2006]
Q.27 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: [JEE 2007]
N.
CO2H
(A) CHO (B) CHO (C) COOH (D)
CO2H
Q.28 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. [JEE 2007]
---------------------------------------------------------------------------------------------------- 16

Mob. No. : 9214233360
Paragraph for Question Nos. 29 to 31(3 questions)
Reimer-Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol,
ortho to the hydroxyl group. This reaction involves electrophilic aromatic substitution. This is
a general method for the synthesis of substituted salicylaldehydes as depicted below:

O Na OH
OH
CHO CHO
aq. HCl
(I)
(Intermediate)
CH3 CH3
CH3
(I) (II) (III)
R
Q.29 Which one of the following reagents is used in the above reaction? [JEE 2007]
(A) aq.NaOH + CH3Cl (B) aq. NaOH +CH2Cl2
(C) aq. NaOH + CHCl3 (D) aq. NaOH + CCl4
Q.30 The electrophile in this reaction is: [JEE 2007]

+
Q.31
(A) : CHCl
(C) : CCl 2
(A)
O Na
CH2Cl
(B)
SI
The structure of the intermediate I is:
 
O Na
CHCl2
(B) CHCl2
(D) : CCl3
(C)

O Na
CCl3
(D)
[JEE 2007]

O Na
CH2OH
J.
CH3 CH3 CH3 CH3
Q.32 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.
[JEE 2007]
Column-I Column-II
N.
(A) C6H5CHO (P) gives precipitate with

2,4- dinitrophenylhydrazine
(B) CH3C CH (Q) gives precipitate with AgNO3
(C) CN– (R) is a nucleophile
–
(D) I (S) is involved in cyanohydrin formation
---------------------------------------------------------------------------------------------------- 17

Mob. No. : 9214233360
Paragraph for Question No.33 to 35
In the following reaction sequence, products I, J and L are formed. K represents a reagent.
1. Mg / ether Cl
1. NaBH 4 2. CO 2 K H2
Hex-3-ynal    I  

 J  Me   L
2. PBr3 3. H3 O Pd / BaSO
O quinoline
4
Q.33 The structure of the product I is: [JEE 2008]

Me
(A) Me Br (B) Br
R
(C) Me Br (D) Me Br
Q.34 The structures of compounds J and K, respectively, are: [JEE 2008]
Q.35
(A) Me
(C)
Me
The structure of product L is:

(A) Me CHO
SI
COOH & SOCl2 (B) Me
COOH & SOCl2 (D) Me
(B) Me
O & SO2Cl2
COOH & CH3SO 2Cl
[JEE 2008]
CHO
J.
CHO
(C) Me (D) Me CHO
Paragraph for Question No.36 to 38
A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I

N.
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
H3C
Ph
M=
H
Ph
Q.36 Compound H is formed by the reaction of : [JEE 2008]

O O
(A) + PhMgBr (C) + PhCH2MgBr
Ph CH3 Ph CH3
O O Me
(C) + PhCH2MgBr (D) +
Ph H Ph H Ph MgBr
---------------------------------------------------------------------------------------------------- 18

Mob. No. : 9214233360
Q.37 The structure of compound I is: [JEE 2008]
Ph CH3 H3C Ph
(A) (B)
H Ph H Ph
Ph CH3 H3C CH3
(C) (D)
H CH2Ph Ph H
Q.38 The structures of compounds J, K and L, respectively are : [JEE 2008]
R
(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. 39 to 41
Q.39
1. MeMgBr
P  SI
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. O3
  Q  

2. H , H2 O
1. OH
 R   S
3. H2SO 4 , 
2. Zn,H2O
The structure of the carbonyl compound P is:

2. 

[JEE 2009]
J.
Me
(A) (B)
O Me O Me
O
(C) (D)
N.
O Et Me
Q.40 The structure of the products Q and R, respectively, are [JEE 2009]
O
Me H
(A) , COMe
Me
Me Me Me
O
H
(B) ,
COMe
Me
Me
Me Me
---------------------------------------------------------------------------------------------------- 19

Mob. No. : 9214233360
O
H
(C) ,
CHO
Et
Me
Me Et
Me O
CH3
(D) ,
CHO
Me
Me Et
R
Q.41 The structure of the product S is : [JEE 2009]
(A)
(C)
Me
Me
O
SI (B)
(D)
Me
O
Me
O
Me
J.
Me
N.
---------------------------------------------------------------------------------------------------- 20

Mob. No. : 9214233360
EXERCISE-4 (B)
NaOC 2H5
Q.1 C6H5 –CHO + CH3 –COOC2H5    (D). [IIT 1995]
C 2H5OH and heat
CH3CH2
(i) KCN/H2SO4
Q.2 C=O D [IIT 1996]
H (ii) LiAlH4
Q.3 Acetophenone on reaction with hydroxylamine- hydrochloride can produce two isomeric
oximes. Write structure of the oximes. [IIT 1997]
Q.4 An aldehyde (A) (C11H8O), which does not undergo self aldol condensation, gives
R
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]
O
O CHC6H5
(C)
Q.5
Q.6
Q.7
O
SI
Base
Identify (A), (B) and (C), and give their structures.

(i )LiAlH
  
4
 (D)
(ii) H , heat
What would be the major product in each of the following reaction? [IIT 2000]
Ph
[IIT 1998]
[IIT 2000]
J.
O
CH3
CH3 Br2
A+B
NaOH
O
H+

C(C7H12O)
Q.8 Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2
N.
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 NaHCO3solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene. [IIT 2002]
Q.9 Write structures of the products A, B, C, D and e in the following scheme.

[IIT 2002]
O
Cl2/FeCl3 Na-Hg HNO3/ H2SO4
CH2CH2CH3 A B C
HCl
– +
Cl CH2= CHCH2O Na H2/ Pd/C
D E
---------------------------------------------------------------------------------------------------- 21

Mob. No. : 9214233360
HCl
Q.10 C6H12 C6H13Cl + (C)
(B)
ozonolysis
(D) (E)
ozonolysis NaOH
(A)    (F) + (G)    NCOONa + 1°alcohol
(D) is isomer 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]
Q.11 Which of the following disaccharide will not reduce. Tollen's reagent?
[IIT 2005]
CH2OH CH2OH HOH2C CH2OH
R
HO O H H O HO OH O H H O OH
(A) (B)
H HO OH H HO OH H
H O H H O H
OH H
(Q)
SI OH H OH H
(P)
H H
J.
N.
---------------------------------------------------------------------------------------------------- 22

Mob. No. : 9214233360
ANSWER KEY
EXERCISE-1
Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. C B C A D B C A B B C B A A B
Q.No. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. B C D C D C C A C B C D C A D
Q.No. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. D C C D B B D D C D C A B C B
Q.No. 46 47 48 49 50 51 52 53
Ans. B C A C B A,B C D
R
EXERCISE-II
Q.No. 1 2 3 4 5 6 7 8 9 10
Ans. C,D B,C A,C,D A,B A,B,C A,B,C,D A,B B,D A,B,C,D B,C
Q.No. 11 12 13 14 15 16 17 18 19 20
Q.1
Ans.
Q.No.
Q.No.
Ans.
B,D
21
Ans. A,B,D
24
D
22
A,D
A
R
SI
A,B
23
B
Q,S
A,B,C
A
P,R
C
S
(a) CH3 – CH2 –CH2 – OH (b) CH3 –CH2 –CH2 –OH

OH OH
A,B
B
P
D
P
EXERCISE-III
B,C,D
C
S
25
A,C,D
D
Q,S
A
P
A,B,C
B
Q
(c) CH3 –CH2 – CH2 – OH

A,D
C
S
A,C,D
D
R
J.
OH
(d) CH3 – CH2 –CH –CH3 (e) CH3 – CH2 –CH –C  CH (f) CH3 – CH2 –CH –Ph
O
(g) CH3 – CH2 –CH –OCH3 (h) CH3 – CH2 –CH
OCH3 O
N.
OH
(i) CH3 –CH2 – CH = NH – PH (j) CH3 – CH2 –CH –N – CH3
CH3
(k) C – C – C= N – OH (l) CH3 –CH2 – CH = N – NH2 (m) CH3 – CH2 –CH2
(n) p- Nitrophenyl hydrazon (o) semi carbazane
OH
(p) CH3 –CH2 – CH = CH – CH3 (q) CH3 – CH2 –CH –CN (r) CH3 – CH2 – CO2H
O
Q.2 (a) C – C – C – C – OH (b) CH3 –CH2 –CH2 –CH = C –CH2 – CH3
CHO
---------------------------------------------------------------------------------------------------- 23

Mob. No. : 9214233360
OH
(c) C – C – C – C = N –OH (d) C – C – C – C – Ph
OH
(e) Ph – CH = C – CH2 – CH3 (f) C – C – C – CH – C  CH
CHO
O
(g) C – C– C – C (h) C – C – C –C
O
(i) 2° alcohol (j) Cyanohydrine (k) 1° alcohol
R
OH
(l) CH3 – CH2 – CH2 –CH – CH –CO2H

Et
Q.3
Q.6
(a) 3 > 2 > 1 > 4
(a)
SI
CH3 – CH – NH –CH2 –CH2–OH
CH3
OH
(b) (i) (CH3)2CCN (ii)
(b)
OH
C6H5CCN
CH3
N
Q.4 R – Mg – X
J.
H
O
(c) CHCl3 + C – OH Q.7 HO  / Br2 ; H2/ Ni; NaOH

N.
Q.8 (a) (i) KMnO4, (ii) CH2 – OH (iii) LiAlH4, (iv) H3O
CH2 – OH
(b) (i) CH2 – OH , (ii) NaBH4, (iii) H3O+, (c) (i) CH2 – OH , (ii) PH3P= CH–Et
CH2 – OH CH2 – OH
(d) (i) H2, (ii) Ni; (e) (i) H2, (ii) Pd–C ; (f) NaBH4
O
O
C –CH3 CHO
CH3
Q.10 (a) (X) CHO (Y) CH3 (b) CH2 – C = CH3
O
O
---------------------------------------------------------------------------------------------------- 24

Mob. No. : 9214233360
O
O Ph
CH
Ph
Q.11 (a) CH3 CH2 – S–CH2–Ph (b)
Cl
O O
O
O CO2H
Q.13 (A) (B) (C)
O
CO2H
CH3 O
R
Br + H–C–C–C–C=C
Q.14 (b) CH3MgBr/ H+,  (c)
(i) Mg (iii) PCC
(ii) H+ (iv) Ph3P = CH3
EXERCISE-IV (A)
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
B
C
1
11
B
21
31
B
37
2
A
12
A,D
22
C
32
38
D
3
13
A
23
D
A
P, S
39
SI 4
B
14
A,B,D
24
C
B
Q
40
D
5
15
B
25
C
C
Q,R, S
41
6
D
16
B, D
26
B
D
Q,R
A
7
17
B
27
A
33
D
B
8
18
B
28
C
34
A
A
9
19
A
29
C
35
C
10
D
20
A
30
C
36
B
J.
Ans. A D B A B
EXERCISE-IV (B)
CH3CH2 OH
C
C6H5CH = CHCOOC2H5
Q. 1 Q.2
(D) H CH2NH2
N.
(a racemic mixture)
Q.3 C6H5 – C – CH3 C6H5 – C – CH3

N – OH and HO – N
syn anti (isomers)
CH= CH –C C – CHO
Ozonolysis
CHO CHO Ag+ COOH
Q.4 +2
COOH COOH
(A) (B) (Oxalic acid)
---------------------------------------------------------------------------------------------------- 25

Mob. No. : 9214233360
Ph Ph
CHC6H5
Q.5 C6H5CHO Q.6 Base
+ Base O O
(C) (D) Br
O O O
CH3 CH3 CH3
C –CH3 Br2 + NaOH COONa + CHBr3
Q.7 O
(A) (B) (C)

O
R
CHO CHO CH2CHO C – CH3 COOH O – CH = CH2
Q.8 (A) or (B) (C) (D) (E)
OCH3 CH2OH OH OH CH3 OH
Q.9 (A)
Cl
Cl
NO2
O
C – Pr
Bu
SI
(B)
Cl
Cl
Bu
NH2
(C)
Cl
NO2
Cl
Bu
J.
Bu
(D)
(E)
Cl Cl
O –CH2 –CH = CH2 O –Pr
Q.10 Me3C – CH = CH2 Me2C – CHMe2 + Me3C – CH–Me

N.
Cl Cl
(A) (B) (C)
alc.KOH
Ozonolysis NaOH
(A) HCHO + Me3C – CHO
(F) (G)
HCOONa + Me3C – CH2OH (1° alcohol)
Q.11 In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in
solution that's why Fehling solution cannot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it
can reduce Fehling solution.
---------------------------------------------------------------------------------------------------- 26

Mob. No. : 9214233360

Carbonyl Compound Worksheet

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EXERCISE-1

Q.1 Gem dihalide on hydrolysis gives :

Q.2 In the given reaction :

(a) and (b) respectively be :

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

(C) III > II > I > IV

Q.5 Acetal or ketal is

Q.6 In the given reaction

(B) a, w-dialkoxy compound

Q.7 In the given reaction

[X] will be-

(A) only synoxime (B) Only anti oxime

Q.8 Schiff's base is prepared from :

Q.9 Schiff's reagent is used for the differentiation between :

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Q.12 In the given reaction

Q.13 Consider the given reaction:

Q.14 Acetone can be converted into pinacol by-

Q.15 Arrange acidity of given four compounds in deceasing order :

(I) CH3 –C – CH2 – C – CH3 (II) CH3 – C – CH3

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(D) CH3 – CHO and CH3 –CHO and CH3 – C – CHO

Q.18 In the reaction :

[X] will be-

Q.19 Product of Perkin reaction is:

(A) , - unsaturated aldehyde (B) -cyclohexyl ,-unsaturated aldehyde

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Q.1 Which one of the following is mixed ketone:

(A) CH3 – C –CH3 (B) CH3 – CH2 –C –CH3

(C) Ph – C –CH3 (D) CH3 – C6H4 – C –CH2Ph

Q.2 In which of the following reactions product will be aldehyde?

Two isomeric ketones, 3-pentanone and 2- pentanone can be distinguished by:

Consider the structure of given alcohol:

This alcohol can be prepared from:

(A) C6H5 – C –CH3 and C2H5MgBr

(B) CH3 – CH2 –C –CH3 and C6H5MgBr

(C) C6H5 – C – C2H5 and CH3MgBr

(D) C6H5 – C –Cl and C2H5MgCl

Q.6 Stability of hydrates of carbonyl compounds depends on:

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(A) C6H5 – C –NHCH3 (B) CH3 – C –NH–C6H5

(C) C6H5 – CH2 –C –NH2 (D) C6H5CH2CN

Q.8 Fehling solution gives red precipitate with:

Q.9 Silver mirror test with Tollen's reagent is given by:

Q.11 Knoevengel rection is catalysed by:

Q.13 Schiff's reagent gives pink colour with:

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(A) Cl & CH3CHO (B) CH3CH2Cl & O

Q.16 Which of the following form stable hemiketal:

Q.20 Acetone give addition elimination reaction with

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List-I (Compound) List- II (Used as)

(C) Allylic bromination (R)

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(D) (i) CHCl3/Alc. KOH/ CHO (S) Gattermann- Koch

(l) CH3–CH2 –CH –COOC2H5 and Zn then H2O/H 

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ethyl orthoformate acetal aldehyde

Q.5 Suggest a reasonable mechanism for each of the following reactions:

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Q.9 Outline reasonable mechanisms for each of the following reactions:

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NaOH/ NaOH/ NaOH/

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