Sem4ch5 Assignment
1.
Identify the reactant X and the product Y
CH 3  CO  CH 3  X  (CH 3 )3 C  OMg  Cl
Hydrolysis
Y  Mg (OH ) Cl
2.
(a) X= MgCl2 Y = CH3CH= CH2
(b) X = CH3MgCl Y = C2H5COCH3
(c) X = CH3MgCl Y = CH3)3 C - OH
(d) X = C2H5MgCl Y = CH3)3C - OH
When m-chlorobenzaldehyde is treated with 50% KOH solution, the product (s) obtained is
(are)
OH OH
CH – CH
(a)
OH
OH
COO 
CH 2 OH
+
(b)
OH
OH
COO 
CH 2 OH
+
Cl
(c)
Cl
OH OH
CH – CH
Cl
Cl
COO 
(d)
CH 2 OH
+
CH
OH
3.
A and B in the following reactions are
B
R  C  R  HCN

 A 

||
KCN
R
R
C
O
(a) A  RR' C
(b)
A  RR' C
(c) A  RR' C
4.
5.
6.
7.
8.
9.
CN
OH
OH
COOH
CN
OH
OH
CH 2 NH 2
, B  LiAlH4
, B  NH 3
, B  H3O
(d) A  RR' CH 2 CN , B  NaOH
Reduction of Aldehydes and Ketones to hydrocarbon take place in the presence of
(a) Zn amalgam and HCl acid
(b) pd by BaSO4
(c) Anhydrous AlCl3
(d) Ni by Pt
Reduction of > C = 0 to CH2 can be carried out with
(a) Catalytic reduction
(b) Na by C2H5OH
(c) Wolf-Kischner reduction
(d) LiAlH4
For C6H5CHO which of the following is incorrect
(a) On oxidation it yields benzoic acid
(b) It is used in perfumery
(c) It is an aromatic aldehyde
(d) On reduction yields phenol
Grignard reagent on reaction with acetone forms
(a) Tertiary alcohol
(b) Secondary alcohol
(c) Acetic acid
(d) Acetaldehyde
Which of the following is incorrect
(a) FeCl3 is used in the detection of phenols
(b) Fehling solution is used in the detection of glucose
(c) Tollens reagent is used in detection of unsaturation
(d) NaHSO3 is used in the detection of carbonyl compounds
Consider the following statement Acetophenone can be prepared by
(1) Oxidation of 1-phenylethanol
(2) Reaction of benzalthanol with methyl magnesium bromide
(3) Friedel crafts reaction of benzene with acetyl chloride
(4) Distillation of calcium benzoate [SCRA 2001]
(a) 1 and 2
(b) 1 and 4
(c) 1 and 3
(d) 3 and 4
10.
Which one of the following pairs is not correctly matched
Clemenson' s reduction
(a)  C  O   CH 2
Wolf- Kishner reduction
  CHOH
(b)  C  O 
Rosenmund' s reduction
 CHO
(c)  COCl 
11.
Stephen reduction

 CHO
(d)  C  N 
Which of the following gives aldol condensation reaction
O
||
(b) C6 H 5  C  C6 H 5
(a) C6H5OH
12.
13.
14.
O
O
||
||
(c) CH 3 CH 2  C  CH 3 (d) (CH 3 )3 C  C  CH 3
Which of the following products is formed when benzaldehyde is treated with CH3MgBr
and the addition product so obtained is subjected to acid hydrolysis
(a) Secondary alcohol (b) A primary alcohol
(c) Phenol
(d) Tert-Butyl alcohol
Aldol condensation will not be observed in[GATE 2001]
(a) Chloral
(b) Phenyl acetaldehyde
(c) Hexanal
(d) Ethanol
Which of the following compounds containing carbonyl group will give coloured crystalline
compound with
NHNH 2
O2 N
(a) CHeCoCl
(c) CH3CO(OC2H5
(e) HO(C6 H 4 )COOH
15.
16.
NO 2
[Kerala (Med.) 2001]
(b) CH3COCH3
(d) CH3CONH2
Which of the following organic compounds exhibits positive Fehling test as well as
iodoform test
(a) Methanal
(b) Ethanol
(c) Propanone
(d) Ethanal
Which of the following compound will undergo self aldol condensation in the presence of
cold dilute alkali
(a) C6H5CHO
(b) CHCH2CHO
(c) CH  C  CHO (d) CH 2  CH  CHO
17.
Acetaldehyde when treated with dilute NaOH gives
(a) CH3CH2OH
(b) CH3COOH
 CH 2  CHO
(c) CH 3  CH
|
OH
18.
19.
20.
(d) CH3 – CH3
C2H5CHO and CH3)2CO can be distinguished by testing with
(a) Phenyl hydrazine (b) Hydroxylamine
(c) Fehling solution
(d) Sodium bisulphite
Which of the following will undergo aldol condensation
(a) Acetaldehyde
(b) Propanaldehyde
(c) Benzaldehyde
(d) Trideuteroacetaldehyde
Which of the following oxidation reactions can be carried out with chromic acid in
aqueous acetone at 5 – 10 C
 CH 3 
(a) CH 3 (CH 2 )3 C  C  CH
|
OH
O
||
CH 3 (CH 2 )3 C C C CH 3
(b) CH 3 (CH 2 )3 CH  CH  CH 2 OH 
CH 3 (CH 2 )3 CH  CH  CHO
(c) C 6 H 5 CH 3  C 6 H 5 COOH
(d) CH 3 (CH 2 )3 CH 2 OH  CH 3 (CH 2 )3 CHO
21.
22.
23.
24.
25.
Acetaldehyde cannot show
[AIIMS 1997]
(a) Iodoform test
(b) Lucas test
(c) Benedict's test
(d) Tollen's test
Benzaldehyde + NaOH
(a) Benzyl alcohol
(b) Benzoic alcohol
(c) Hydrobenzamide (d) Cinnamic acid
The following reagent converts C6H5COCHO to C6H5CHOHCOONa
(a)Aq. NaOH
(b)Acidic Na2S2O3
(c)Na2CrO4 by H2SO4 (d)NaNO2 by HCl
Benzyl alcohol and sodium benzoate is obtained by the action of sodium hydroxide on
benzaldehyde. This reaction is known as
(a) Perkins reaction
(b) Cannizzaros reaction
(c) Sandmeyer’s reaction
(d) Claisen condensation
To distinguish between formaldehyde and acetaldehyde we require
(a) Tollens reagent
(b) Fehlings solution
(c) Schiffs reagent
(d) Caustic soda solution
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
Which of the following does not give iodoform test
(a) CH3CH2OH
(b) CH3OH
(c) CH3CHO
(d) PhCOCH3
Which of the following will not give iodoform test
(a) Ethanal
(b) Ethanol
(c) 2 propanone
(d) 3-pentanone
Which of the following will not give the iodoform test
(a) Acetophenone
(b) Ethanal
(c) Benzophenone
(d) Ethanol
Haloform test is given by the following substance
(a) HCHO
(b) (CH 3 )2 CO
(c) CH3OCH3
(d) CH3CH2Cl
Dimethyl ketones are usually characterised through
(a) Tollens reagent
(b) Iodoform test
(c) Schiffs test
(d) Benedicts reagent
The light yellow compound produced when acetone reacts with iodine and alkali, is
(a) CH3COCH2I
(b) CH3I
(c) CHI3
(d) None of these
If formaldehyde and KOH are heated then we get
(a) Acetylene
(b) Methane
(c) Methyl alcohol
(d) Ethyl formate
Which of the following reagent reacts differently with HCHO, CH3CHO and CH3COCH3
(a) HCN
(b) NH2NH2
(c) NH2OH
(d) NH3
Acetaldehyde reacts with C2H5MgCl the final product is
(a) An aldehyde
(b) A ketone
(c) A primary alcohol (d) A secondary alcohol
Treatment of propionaldehyde with dilute NaOH solution gives
(a) CH3CH2COOCH2CH2CH3
(b) CH3CH2CHOHCH(CH3)CHO
(c) CH3CH2CHOHCH2CH2CHO
(d) CH3CH2COCH2CH2CHO
Aldol condensation of acetaldehyde involves the formation of which of the following
intermediate
(a) Acetate ion
(b) A carbanion
(c) A carbonium ion (d) A free radical
HCl
3CH 3 COCH 3 
(CH 3 )2 C  CH  CO  CH  C(CH 3 )2
This polymer (B) is obtained when acetone is saturated with hydrogen chloride gas, B can
be
(a) Phorone
(b) Formose
(c) Diacetone alcohol (d) Mesityl oxide
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
Aromatic aldehydes undergo disproportionation in presence of sodium or potassium
hydroxide to give corresponding alcohol and acid. The reaction is known as
(a) Wurtzs reaction
(b) Cannizzaro reaction
(c) Friedel-Crafts reaction (d) Claisen reaction
m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives
(a) Potassium m-chlorobenzoate and m-hydroxy benzaldehyde
(b) m-hydroxy benzaldehyde and m-chlorobenzyl alcohol
(c) m-chlorobenzyl alcohol and m-hydroxy benzyl alcohol
(d) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
Which of the following does not give yellow precipitate with NaOH+KI
(a) Acetone
(b) Acetaldehyde
(c) Benzaldehyde
(d) Acetophenone
The alkaline CuSO4 containing sodium potassium tartrate does not react with
(a) CH3CHO
(b) C2H5CHO
(c) C6H5CH2CHO
(d) C6H5CHO
Correct order of reactivity of CH3CHO, C2H5COCH3 and CH3COCH3 is
(a) CH 3CHO  CH 3COCH 3  CH 3COC2 H5
(b) C2 H5 COCH 3  CH 3COCH 3  CH 3CHO
(c) CH 3COCH 3  CH 3CHO  C2 H5 COCH 3
(d) CH 3COCH 3  C2 H5 COCH 3  CH 3CHO
One mole of an organic compound requires 0.5 mole of oxygen to produce an acid. The
compound may be
(a) Alcohol
(b) Ether
(c) Ketone
(d) Aldehyde
Aldehydes can be oxidised by
(a) Tollens reagent
(b) Fehling solution
(c) Benedict solution (d) All of these
Silver mirror is a test for
(a) Aldehydes
(b) Thio alcohols
(c) Amines
(d) Ethers
CH3CH = CHCHO is oxidised to CH3CH = CHCOOH using
(a) Alkaline KMnO4
(b) Selenium dioxide
(c) Ammoniacal AgNO3
(d) All of these
Which of the following does not turn Schiffs reagent to pink
(a) Formaldehyde
(b) Benzaldehyde
(c) Acetone
(d) Acetaldehyde
Fehlings test is positive for
(a) Acetaldehyde
(b) Benzaldehyde
(c) Ether
(d) Alcohol
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
Acetaldehyde and acetone differ in their reaction with
(a) Sodium bisulphite
(b) Ammonia
(c) Phosphorus pentachloride
(d) Phenyl hydrazine
The final product formed when acetaldehyde is reduced with sodium and alcohol is
(a) Ethylene
(b) Ethyl alcohol
(c) Ethene
(d) All of these
The compound obtained by the reduction of propionaldehyde by amalgamated zinc and
concentrated HCl is
(a) Propanol
(b) Propane
(c) Propene
(d) All of these
Formaldehyde when treated with KOH gives methanol and potassium formate. The
reaction is known as
(a) Perkin reaction
(b) Claisen reaction
(c) Cannizzaro reaction (d) Knoevenagel reaction
Aldehydes and ketones give addition reaction with
(a) Hydrazine
(b) Phenyl hydrazine
(c) Semicarbazide
(d) Hydrogen cyanide
(e) All of these
Acetaldehyde reacts with
(a) Electrophiles only
(b) Nucleophiles only
(c) Free radicals only
(d) Both electrophiles and nucleophiles
The typical reactions of aldehyde is
(a) Electrophilic addition (b)Nucleophilic substitution
(c) Nucleophilic addition (d)Nucleophilic elimination
Which will not give acetamide on reaction with ammonia
(a) Acetic acid
(b) Acetyl chloride
(c) Acetic anhydride (d) Methyl formate
The addition of HCN to carbonyl compounds is an example of
(a) Nucleophilic substitution
(b) Electrophilic addition
(c) Nucleophilic addition
(d) Electrophilic substitution
Which of the following reagents is used to distinguish acetone and acetophenone
(a) NaHSO3
(b) Grignard reagent
(c) Na2SO4
(d) NH4Cl
59.
60.
61.
62.
63.
The product formed by the reaction of chlorine with benzaldehyde in the absence of a
catalyst is
(a) Chlorobenzene
(b) Benzyl chloride
(c) Benzoyl Chloride
(d) o-Chlorobenzaldehyde
Which of the following compound is resistant to nucleophilic attack by hydroxyl ions
(a) Methyl acetate
(b) Acetonitrile
(c) Dimethyl ether
(d) Acetamide
Glucose molecule reacts with X number of molecules of phenylhydrazine to yield osazone.
The value of X is
(a) One
(b) Two
(c) Three
(d) Four
In which of the following reactions aromatic aldehyde is treated with acid anhydride in
presence of corresponding salt of the acid to give unsaturated aromatic acid
(a) Friedel-Craft's reaction (b) Perkin reaction
(c) Wurtz reaction
(d) None of these
Hg
2CH 3  C  CH 3 Mg
/
 Product, product in the reaction is

||
H
O
CH 3 CH 3
|
|
 O  C  CH 3
(a) H 3 C  C  C|  CH 3 (b) CH 3  C
||
||
|
O
O
OH OH
 CH  CH 3
(c) CH 3  CH
|
|
(d)
None of these
OH OH
64.
65.
66.
Cinnamic acid is formed when C6 H5  CHO condenses with (CH 3 CO )2 O in presence of
(a) Conc. H2SO4
(b) Sodium acetate
(c) Sodium metal
(d) Anhydrous ZnCl2
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
The reaction,
O
||
H  or OH 
CH 3  C  OCH 3  C 2 H 5 OH 
O
||
CH 3  C  OC2 H 5  CH 3 OH is called[MP PMT 2003]
(a) Perkins reaction
(b) Claisen Schmidt reaction
(c) Esterification
(d) Trans-esterification
67.
68.
69.
70.
71.
72.
73.
74.
75.
Formaldehyde reacts with ammonia to give urotropine. The formula of urotropine is
(a) (CH 2 )6 N 4
(b) (CH 2 )4 N 3
(c) (CH 2 )6 N 6
(d) (CH 2 )3 N 3
Aldol condensation will not take place in
(a) HCHO
(b) CH3CH2CHO
(c) CH3CHO
(d) CH3COCH3
Contents of three bottles were found to react
(i) Neither with Fehling's solution nor with Tollens reagent
(ii) Only with Tollen's reagent but not with Fehling's solution
(iii) With both Tollen's reagent and Fehling's solution.If they contained either ethanal
(acetaldehyde) or propanone (acetone) or benzal (benzaldehyde), which bottle
contained which
(a) In (i) benzal, in (ii) ethanal and in (iii) propanone
(b) In (i) benzal, in (ii) propanone and in (iii) ethanal
(c) In (i) propanone, in (ii) benzal and in (iii) ethanal
(d) In (i) propanone, in (ii) ethanal and in (iii) benzal
Action of hydrazine on aldehydes and ketones gives compound of the general structure
(a) > C = N – NH2
(b) > C = N - OH
(c) > C = N – NH – CONH2
(d) > C = N – NH – C6H5
The reaction in which sodium cyanide is used
(a) Perkin reaction
(b) Reimer-Tiemann reaction
(c) Benzoin condensation (d)Rosenmund reaction
Which one of the following reactions is a method for the conversion of a ketone into a
hydrocarbon
(a) Aldol condensation (b) Reimer-Tiemann reaction
(c) Cannizzaro reaction (d) Wolf-Kishner reduction
Bakelite is a polymer of
(a) HCHO + phenol
(b) HCHO + aldehyde (acetaldehyde)
(c) Phenol+ H2SO4
(d) HCHO + acetone
Clemmenson reduction involves > C = O to > CH2 in presence of
(a) Zn / Hg
(b) Alcohol
(c) Zn dust
(d) Zn / alcohol
Aldol condensation involving CH3CHO + CH3CHO gives the product
(a) CH3CHOHCH2CHO
(b) CH3COCH2CH3
(c) CH3CH = CH2
(d) None of these
76.
77.
78.
79.
Enol content is highest in
(a) Acetone
(b) Acetophenone
(c) Acetic acid
(d) Acetyl acetone
Which one of the following reacts with HCN and Tollens reagent, but is not oxidised by
Fehling's solution
(a) Methanal
(b) Ethanal
(c) Benzaldehyde
(d) Acetone
During reaction of benzaldehyde with alkali one of the product is
(a) Phenol
(b) Benzyl alcohol
(c) Benzene
(d) Benzophenone
Cannizzaro reaction is given by
(a) HCHO
(c) CH3CHO
80.
(b) CH3COCH3
(d) CH3CH2OH
The reaction
C 6 H 5 CHO  CH 3 CHO  C 6 H 5 CH  CH  CHO
81.
82.
is known as
(a) Perkins reaction
(b) Claisen condensation
(c) Benzoin condensation
(d) Cannizzaros reaction
When two molecules of acetaldehyde condense in the presence of dilute alkali it forms
(a) Acetal
(b) Sodium formate
(c) Aldol
(d) Mesitylene
(e) None of these
Acetaldehyde on treatment with dil. NaOH followed by heating gives
(a) CH3CH2Ch2CH2OH
(b) CH3CH2CH2CHO
(c) CH3 - CH = CHCHO
(d) CH3 – CH = CHCH2OH
R
83.
R
Reaction R
(a)
(b)
(c)
(d)
|
CO  HCN  R  C  OH is
|
CN
Electrophilic substitution
Electrophilic addition
Nucleophilic addition
Nucleophilic substitution
84.
85.
86.
87.
88.
89.
90.
91.
92.
93.
94.
Benzaldehyde on reaction with acetophenone in the presence of sodium hydroxide
solution gives
(a) C6H5CH = CHCOC6H5
(b) C6H5COCH2C6H5
(c) C6H5CH = CHC6H5
(d) C6H5CH(OH)COC6H5
Aldehydes and ketones can be reduced to hydrocarbon by using
(a) LiAlH4
(b) H2 by Pd – BaSO4
(c) Na – Hg by HCl
(d) NH2 – NH2 by C2H5ONa
An important reaction of acetone is autocondensation in presence of concentrated
sulphuric acid to give the aromatic compound
(a) Mesitylene
(b) Mesityl oxide
(c) Trioxan
(d) Phorone
Identify the organic compound which, on heating with strong solution of NaOH, partly
converted into an acid salt and partly into alcohol
(a) Benzyl alcohol
(b) Acetaldehyde
(c) Acetone
(d) Benzaldehyde
Which of the following does not give brick red precipitate with Fehling solution
(a) Acetone
(b) Acetaldehyde
(c) Formalin
(d) D glucose
Acetaldehyde and acetone can be distinguished by
(a) Molisch test
(b) Bromoform test
(c) Solubility in water (d) Tollen's test
Which compound is soluble in H2O
(a) HCHO
(b) CH3CHO
(c) CH3COCH3
(d) All
H 2O
CH 3 CHO  CH 3 MgBr  Product 
 A
What is A ?
(a) Primary alcohol
(b) Secondary alcohol
(c) Tertiary alcohol
(d) Ketone
Which gives lactic acid on hydrolysis after reacting with HCN
(a) HCHO
(b) CH3CHO
(c) C6H5CHO
(d) CH3COCH3
CH3CHO react with aqueous NaOH solution to form
(a) 3-hydroxy butanal (b) 2-hydroxy butanal
(c) 4-hydroxy butanal (d) 3-hydroxy butanol
Fehling solution react with HCHO to form precipitate of
(a) White colour
(b) Yellow colour
(c) Red colour
(d) Blue colour
95.
96.
Product in following reaction is
CH 3 MgI  HCHO  Product
(a) CH3CHO
(b) CH3OH
(c) C2H5OH
(d) CH3 – O – CH3

A 
CH 2  C  O , Reactant ‘A’ in the reaction is
800 o C
(a) CH3CH2CHO
(b) CH3CHO
 CH 3
(c) CH 3  C
||
(d) C2H5OH
O
97.
98.
99.
Only an aldehyde having..... can undergo the aldol condensation
(a) At least one beta H atom
(b) At least one alpha H atom
(c) An aromatic ring
(d) No alpha H atom
Clemensons reduction of ketones is carried out in
(a) H2 with Pd catalyst (b) Glycol with KOH
(c) LiAlH4 in water
(d) Zn - Hg with HCl
Reaction
R
R
100.
H 2 NNH 2
C  O 


KOH / glycol
R
R
C
H
H
 N 2  H 2 is called
(a) Wolff–Kishner reaction
(b) Tischenko reaction
(c) Reformatsky reaction
(d) Gattermann reaction
Propanal on treatment with dilute sodium hydroxide forms
(a) CH3CH2CH2CH2CH2CHO
(b) CH 3CH 2CH (OH)CH 2CH 2CHO
(c) CH 3CH 2CH (OH)CH (CH 3 )CHO
(d) CH 3CH 2COONa
Answers:
1
c
2
c
3
a
4
a
5
c
6
d
7
a
8
c
9
c
10
b
11
c
12
a
13
a
14
b
15
d
16
b
17
c
18
c
19
abd
20
abcd
21
b
22
a
23
a
24
b
25
d
26
b
27
d
28
c
29
b
30
b
31
c
32
c
33
d
34
d
35
c
36
b
37
a
38
b
39
d
40
c
41
d
42
a
43
d
44
d
45
a
46
c
47
c
48
a
49
b
50
b
51
b
52
c
53
d
54
b
55
c
56
d
57
c
58
a
59
c
60
c
61
b
62
b
63
a
64
b
65
a
66
d
67
a
68
a
69
c
70
a
71
c
72
d
73
a
74
a
75
a
76
d
77
c
78
b
79
a
80
b
81
c
82
c
83
c
84
a
85
d
86
a
87
d
88
a
89
d
90
d
91
b
92
b
93
a
94
c
95
c
96
a
97
b
98
d
99
a
100 c