TG: @Chalnaayaaar

TG: @Chalnaayaaar

Aldehyde, Ketone and Carboxylic Acid Part-01
Aldehyde, Ketone and Carboxylic Acid DPP-01
1. Which reagent below cannot reduce an acid chloride to an aldehyde?

(1) H2/Pd-BaSO4
(2) NaH
(3) LiAlH4
(4) DI BAL-H
2. Compound which gives only acetone on ozonolysis

(1) CH3–CH=CH–CH3
(2) (CH3)2C=C(CH3)2
(3)
(4) CH3CH=CH2
H2
3. CH3COCl ⎯⎯⎯⎯⎯⎯⎯ → CH3CHO + HCl;
Pd/BaSO 4
The above reaction is called
(1) Reimer-Tiemann reaction
(2) Cannizzaro reaction
(3) Rosenmund reaction
(4) Reformatsky reaction
4. Which of the following when passed through warm dilute solution of H 2SO4 in presence of HgSO4 gives
acetaldehyde?
(1) CH3–CCH
(2) CH2=CH2
(3) CHCH
(4) CH3–CH3
5. Catalyst SnCl2/HCl is used in

(1) Stephen’s reduction
(3) Clemmensen reduction
(4) Rosenmund’s reduction
6 Hydrogenation of benzoyl chloride in the presence of Pd gives

(1) Benzyl alcohol
(2) Benzaldehyde
(3) Benzoic acid
(4) Phenol
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TG: @Chalnaayaaar
HgSO 4
7. CH3—CH2—CCH ⎯⎯⎯⎯⎯ → A, the compound A is
H2SO 4
O
(1) CH3—CH2—C—CH3
(2) CH3—CH2—CH2—CHO
(3) CH3—CH2—CH2—COOH
OH
(4) CH3—CH2—C=CH2
8. In aldehydes and ketones, carbon of carbonyl group is

(1) sp3 hybridised
(2) sp2 hybridised
(3) sp hybridised
(4) Unhybridised

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7 8
Answer 3 2 3 3 1 1 1 2
SOLUTIONS DPP-01
O O
X
1. R—C—Cl R—C—H
acid chloride aldehyde
X can be H2/Pd-BaSO4, NaH, DIBAL-H
but when LiAlH4 is used, it yields alcohol.
CH3 OO CH3 CH3 CH3

Ozonolysis
2. C=C C=O + O=C
CH3 CH3 CH3 CH3
3. Conversion of acid chloride to aldehyde in the presence of H 2/Pd-BaSO4 is called Rosenmund reaction.
O
dil.H2SO4
4. HCCH H3C—C—H
1%HgSO4
(Acetaldehyde)
5. The catalyst SnCl2/HCl is used in Stephen’s reduction.
H2/Pd H2/Pd
C—Cl C—H CH2—OH
6.
O O
(Benzoyl chloride) (Benzyl alcohol)
O
HgSO4
7. CH3—CH2—CCH CH3—CH2—C—CH3
H2SO4
8. In aldehyde and ketones, the carbonyl group is sp2 hybridised.

TG: @Chalnaayaaar
1. Benzaldehyde as a major product can be prepared by oxidation of toluene by

(1) Acidic KMnO4
(2) K2Cr2O7
(3) CrO3
(4) All of these
2. The reagent used in Gattermann-Koch aldehyde synthesis is

(1) Pb/BaSO4
(2) alkaline KMnO4
(3) acidic KMnO4
(4) CO + HCl
3. The oxidation of toluene to benzaldehyde by chromyl chloride is called

(2) Wurtz reaction
(3) Etard reaction
(4) Reimer-Tiemann reaction
4. Which reaction does not give ketone as a major product?
+ CH3—C—H AlCl3
(1)
O
Cl
(2) CH3—C— CH3 + aq.KOH
Cl
CH3
(3) + CO + H—Cl AlCl3
CH2–CH3
(4) + 2Cl2 hv H2O
A
hv H2O
5. Ph—CH3 + 2Cl2 ⎯⎯⎯ → A ⎯⎯⎯⎯ → ?
(1) Ph—CHO
(2) Ph—COOH
(3) Ph—CH2–OH
(4) Ph—COCl

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5
Answer 3 4 3 3 1
SOLUTIONS DPP-02
1. CrO3 will oxidise —CH3 into —CHO group.
2. The reagant used in gattermann-Koch aldehyde syntheses is CO + HCl.
3. The oxidation of toluene to benzaldehyde by chromyl chloride is called etard reaction

CH3 CHO
(i) CrO2Cl2 / CS2
(ii) H3O+
Toluene benzaldehyde
4. Option (3) is Gattermann Koch Aldehyde synthesis.
5.

TG: @Chalnaayaaar
1. Which of the following reacts with dialkyl cadmium to give ketone as products?
O
(1) R—C—Cl
O O
(2) R—C—O—C—R
O
(3) R—C—OR
O
(4) R—C—NH2
2.
(1) Ph—C—CH3
O
CH3
(2) Ph—C—CH3
OH
(3) Ph—CH—CH3
OH
COCl
(4)
CH3

H3 O
3. CH3—CN + CH3MgBr ⎯→ A ⎯⎯⎯⎯ → ?
(1) CH3—COOH
(2) CH3—COCH3
(3) CH3—C=NH
CH3
CH3
(4) CH3—C—NH2
CH3

TG: @Chalnaayaaar
4. Product when methyl propanoate reacted with phenyl magnesium bromide?

(1) CH3—C—Ph
O
(2) CH3—CH2—C—Ph
O
(3) CH3—CH—OH
Ph
(4) CH3—CH2—CH—Ph
OH
5. Which have maximum boiling point?

(1) CH3—CH2—CHO
(2) CH3—COCH3
(3) CH3—CHO
(4) H—CHO
C N
(i) DIBAL-H
6.
(ii) H2O
CHO
(1)
CHO
(2)
CH2–OH
(3)
CH2–OH
(4)

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6
Answer 1 1 2 2 2 1
SOLUTIONS DPP-03
O O
1. 2 R—C—Cl + Cd(R’)2 2 R—C—R’ + 2 CdCl2

Acid chloride dialkyl ketone
cadmium
2. Ph—C—Cl + CH3MgCl Ph—C—CH3
O O
H H–OH
3. CH3—CN + CH3MgCl CH3—C=NMgBr CH3—C=NH CH3—C=O + NH3
H
CH3 CH3 CH3
4. CH3—CH2—C—O—CH3 + PhMgBr CH3—CH2—C—Ph
O O
Methyl propanoate
5. Boiling point  M.W.

and ketone > Aldehyde
6. DIBAL-H → only one hydride is available and it does not reduce alkene
O
CN C—H
DiBAL-H
H2O

TG: @Chalnaayaaar
1. Correct order of reactivity of CH3CHO, C2H5COCH3 and CH3COCH3 is

(1) CH3CHO > CH3COCH3 > CH3COC2H5
(2) C2H5COCH3 > CH3COCH3 > CH3CHO
(3) CH3COCH3 > CH3CHO > C2H5COCH3
(4) CH3COCH3 > C2H5COCH3 > CH3CHO
2. Acetaldehyde reacts with

(1) Electrophiles only
(2) Nucleophiles only
(3) Free radicals only
(4) Both electrophiles and nucleophiles
3. The addition of HCN to carbonyl compounds is an example of

(1) Nucleophilic substitution
(2) Electrophilic addition
(3) Nucleophilic addition
(4) Electrophilic substitution
4. Arrange the following compounds in decreasing order of nucleophilic addition reaction:

O O O O
H—C—H H3C—C—H H3C—C—CH3 C—CH3
(I) (II) (III) (IV)

(1) II > IV > III > I
(2) I > II > III > IV
(3) IV > III > II > I
(4) II > III > IV > I
5. Arrange the compounds in order of decreasing reactivity nucleophilic addition reaction:

O O O
Ph—CHO Cl—CH2—C—H H—C—H CCl3—C—H
(I) (II) (III) (IV)
(1) IV > II > III > I
(2) I > II > III > IV
(3) II > III > I > IV
(4) II > I > III > IV

TG: @Chalnaayaaar
NaCN
6. CH3—CH2—C—CH3
HCl
O
CN
(1) CH3—CH2—C—CN
OH
COOH
OH
(3) CH3—CH2—C—CN
O
CN
Cl
7. Which gives racemic mixture when reacted with HCN?

(1) H—CHO
(2) Ph—COPh
(3) —C—
(4) C—CH3

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7
Answer 1 4 3 2 1 1 4
SOLUTIONS DPP-04
1. In carbonyl compounds,
Reactivity  electrophilicity of carbonyl group
1

sterichindrance
 more the number of electron donating groups attached to carbonyl group, less will be the reactivity.
The correct order will be
CH3CHO > CH3COCH3 > CH3COC2H5
2. CH3—C—H can reacts with both electrophile as well as nucleophile.

(Acetaldehyde)
••
O OH OH
H Nu
CH3—C—H CH3—C—H CH3—C—H
(Acetaldehyde)
Nu
3. The addition of HCN to carboxylic compounds is an example of nucleophilic addition where CN Θ acts as a
nucleophile.
1

sterichindrance
 more the number of electron donating groups attached to carbonyl group, less will be the reactivity.
The correct order will be
O O O O
H—C—H > H3C—C—H > H3C—C—CH3 > C—CH3
O O O O
CCl3—C—H > Cl—CH2—C—H > H—C—H > Ph—C—H

TG: @Chalnaayaaar
6. NaCN + HCl ⎯→ NaCN + HCl

CN
(ii) H
CH3—CH2—C—CH3 + CN CH3—CH2—C—CH3
O OH
CN
7. C—CH3 + HCN C—CH3
O OH
One chiral carbon (mixture of d + )
Product of remaining compound have no chiral carbon.

TG: @Chalnaayaaar
1. From which of the following tertiary butyl alcohol is obtained by the action of methyl magnesium iodide
(1) HCHO
(2) CH3CHO
(3) CH3COCH3
(4) CO2
2. Acetaldehyde reacts with C2H5MgCl the final product is

(1) An aldehyde
(2) A ketone
(3) A primary alcohol
(4) A secondary alcohol
3. Which gives lactic acid on hydrolysis after reacting with HCN?

(1) HCHO
(2) CH3CHO
(3) C6H5CHO
(4) CH3COCH3
4. Identify the product Y in the sequence

Ether H2O/H+
CH3CHO + CH3MgI ⎯⎯⎯⎯→ X ⎯⎯⎯⎯⎯⎯ → Y
(1) CH3OH
(2) CH3CH2OH
(3) (CH3)2CHOH
(4) (CH3)3COH
5. Which of the following compound does not react with NaHSO3?

(1) C6H5CHO
(2) C6H5COPh
(3) CH3COCH3
(4) C2H5COCH3

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5
Answer 3 4 2 3 2
SOLUTIONS DPP-05
CH3 CH3
H–OH
1. CH3—C—CH3 + CH3MgI CH3—C—CH3 CH3—C—CH3
O OMgI OH
3º Alcohol
CH2–CH3
H–OH
2. CH3—C—H + CH3—CH2MgCl CH3—CH CH3—CH—CH2—CH3
O OMgCl OH
2º Alcohol
CN COOH
H3O
3. CH3—C—H + H—CN CH3—C—H CH3—C—H
O OH OH
Lactic acid
CH3
H–OH
4. CH3—CH + CH3MgI CH3—CH CH3—CH—CH3
O OMgI OH
2ºAlcohol
5. Ph—C—C6H5 does not react with NaSCO3
O
Benzylic ketone

TG: @Chalnaayaaar
1. Which gives stable hydrate?

(1) CH3—C—H
O
(2) Ph—CHO
(3) CCl3—CHO
(4) CH3—C—CH3
Ph—CHO + EtOH excess H

2.
(1) Ph—CH2—OEt
(2) Ph—C—OCH2—CH3
O
(3) Ph—CH(OEt)2
(4) Ph—CH—OEt
OH
CH3 O—CH2
3. H3O
C
CH3 O—CH2
(1) CH3—C—CH3 + CH2—OH
O CH2—OH
OH
(2) CH3—C—CH3 + CH2
OH
O
(3) CH3—C—CH2—CH2—OH + CH3—OH
O
(4) CH3—C—CH3 + CH2—OH
HO OH CH2—OH
Ph—CHO + Ph—NH2 H
4.
(1) Ph—CH2—Ph
(2) Ph—CH2—NH2
(3) Ph—CH=NH—Ph
(4) Ph—CH2—NH—Ph

TG: @Chalnaayaaar
5. Which is the best nucleophile

1 2 3
NH2—C—NH—NH2
O
(1) 1
(2) 2
(3) 3
(4) all are same
6. Which gives DNP test?

(1) Ph—CO—CH3
(2) Ph—CHO
(3) CH3—COCH3—CH3
(4) all of these
7. Which gives two oxime when reacted with NH2—OH?

(1) H—CHO
(2) Ph—COPh
(3) CH3—COCH3
(4) Ph—COCH3

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7
Answer 3 3 1 3 3 4 4
SOLUTIONS DPP-06
1. Hydrate of CCl3–CHO is stable due to H-bonding.

Cl HO
CCl3—C—H + H–OH Cl—C C—H
Cl H—O
O
H–OEt OEt
-H2O
2. Ph—CH=O + Ph–CH
H–OEt OEt
HO H
••
CH3 O—CH2 CH3
3. C C=O + CH2 CH2
CH3 O—CH2 CH3
OH OH
HO H
4. Ph—CH=O + H2N—Ph -H2O Ph–CH=N—Ph
5. In 3 lone pair of nitrogen not involved in resonance.
6. All aldehyde and ketone gives DNP test.
Ph Ph
-H2O
7. C=O + H2N—OH C=N—OH
CH3 CH3
Shows G.I.
 2 products obtained.

TG: @Chalnaayaaar
1. The Clemmensen reduction of acetone yields

(1) Ethanol
(2) Ethanal
(3) Propane
(4) Propanol
2. Which of the following reagent can be used for the following conversion?
O
(1) Red P/HI/

(2) Zn-Hg/HCl
(3) NH2—NH2/ –OH
(4) All of these
3. Which does not give Tollen’s Test?

(1) HCHO
(2) CH3COCH3
(3) CH3CHO
(4) CH3CH2CHO
4. Reaction
R H2N NH2 R H
C= O KOH/glycol
C + N2 + H2
R R H
is called
(1) Wolff–Kishner reaction
(2) Tischenko reaction
(3) Reformatsky reaction
(4) Gattermann reaction
5. C2H5CHO and (CH3)2CO can be distinguished by

(1) phenyl hydrazine
(2) Hydroxylamine
(3) Fehling solution
(4) Sodium bisulphite
6. Tollens regent used for the distinction of aldehydes and ketones is

(1) Cu(II) citrate –NH3 (aq)
(2) Cu(NO3)2 –NH3 (aq)
(3) Pb(NO3)2 –NH3 (aq)
(4) AgNO3 –NH3 (aq)

TG: @Chalnaayaaar
7. Which reagent can differentiate acetaldehyde and acetophenone?

(1) Benedict solution
(2) [Ag(NH3)2+]
(3) NaHSO3
(4) All of these
8. Which is the most suitable reagent for the reaction?

OH OH
CHO COOH
(1) AgNO3–NH3 (aq)
(2) KMnO4–NaOH
(3) KMnO4–H2SO4
(4) CrO3–H2SO4
9. When acetaldehyde is heated with Fehling’s solution it gives a precipitate of

(1) Cu
(2) CuO
(3) Cu2O
(4) Cu + Cu2O + CuO
10. Which of the following does not turn Schiff’s reagent to pink?
(1) Formaldehyde
(2) Benzaldehyde
(3) Acetone
(4) Acetaldehyde

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7 8 9 10
Answer 3 4 2 1 3 4 4 1 3 3
SOLUTIONS DPP-07
Zn–Hg
1. CH3—C—CH3 CH3—CH2—CH3
HCl
(Propane)
O
In Clemmensen reduction —C— is converted in –CH2–
2. All converts —C— in –CH2–
3. Ketone does not give Tollens' Reagent test. Only aldehyde reduces Tollens' Reagent
4. Reduction of aldehyde/Ketone in Alkane by NH2–NH2/ –OH is known as wolff kishner.
5. Phenyl hydrazine → reacts with all aldehyde/ketone

Hydroxyl amine → reacts with all aldehyde/ketone
Sodium bisulphite → reacts with all aldehyde and aliphatic methyl ketone
Fehling solution → reacts only with aliphatic aldehyde
6. Tollens' reagent means → AgNO3 + NH4OH or AgNO3 + NH3 (aq.)
7. Benedict solution → reacts with only aldehyde

NaHSO3 → reacts with acetaldehyde not with acetophenone
[Ag(NH3)2]+ → reacts with acetaldehyde not with ketone.
So answer is option (4)
8. KMnO4/H2SO4, CrO3/H2SO4
KMnO4/NaOH also oxidise alcohol
So not used (-OH should be retained according to question)
AgNO3 + NH3 (aq.) → not reacts with –OH
So answer is option (1)
9. CH3—CHO + CuSO4 CH3—COOH + Cu2O

(F.S.) +1
+2 Red
Blue
10. Only aldehyde reacts with schiff’s reagent.

TG: @Chalnaayaaar
1. The compound that will not give iodoform on treatment with alkali and iodine is:
(1) Acetone
(2) Ethanol
(3) Diethyl ketone
(4) Isopropyl alcohol
2. Which of the following will not give the iodoform test?

(1) Acetophenone
(2) Ethanal
(3) Benzophenone
(4) Ethanol
3. Which of the following give yellow precipitate with NaOH+I2?

(1) Acetone
(2) CH3—C—Cl
O
(3) Benzaldehyde
(4) CH3—C—O—CH3
4. How will you convert butan-2-one to propanoic acid?

(1) Tollens reagent
(2) Felling’s solution
(3) NaOH/I2/ and H+
(4) NaOH/NAI/H+
C—CH3 NaOH
5. P.P.T.
O I2
PPT of-
(1) CH3I
(2) CHI3
I
(3)
(4) CH2I2

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5
Answer 3 3 1 3 2
SOLUTIONS DPP-08
O
1. Iodoform test is given by those compounds which has —C—CH3 group and also those alcohols which produces
O
CH3—C— group on oxidation. In Diethyl ketone we have CH3—CH2— group on both sides hence, It will not
give iodoform test.
O
O
CH3—C— group on oxidation. Benzophenone contain phenyl group on both sides hence, It will not give
iodoform test.
O
O
CH3—C— group on oxidation. Benzaldehyde contain phenyl group therefore It will not give yellow ppt. with
NaOH + I2 Solution
O O
4. (i) NaOH/I2,
CH3—C—CH2—CH3 CH3—CH2—C—OH + CHI3
(ii) H
Butan-2-one Propanoic acid yellow ppt.
5. yellow ppt of CHI3 is obtained.

TG: @Chalnaayaaar
1. Which of the following could result as a product in the aldol condensation reaction?
(1) 4-methyl-5-hexen-2-one
(2) 4-methyl-4-penten-2-one
(3) 4-methyl-3-penten-2-one
(4) 3-methyl-4-hexen-2-one
2. Which of the following gives aldol condensation reaction?

(1) C6H5OH
O
(2) C6H5—C—C6H5
O
(3) CH3CH2—C—CH3
O
(4) (CH3)3C—C—C(C2H5)3
3. Aldol condensation will not be observed in

(1) Chloral
(2) Phenyl acetaldehyde
(3) Hexanal
(4) Acetophenone
4. Which of the following compound will undergo self-aldol condensation in the presence of dilute alkali?
(1) C6H5CHO
(2) CH3CH2CHO
(3) CHC—CHO
(4) CH2=CH—CHO
5. Acetaldehyde when treated with dilute NaOH gives

(1) CH3CH2OH
(2) CH3COOH
(3) CH3—CH—CH2—CHO
OH
(4) CH3—CH3
6. Treatment of propionaldehyde with dilute NaOH Solution gives

(1) CH3CH2COOCH2CH2CH3
(2) CH3CH2CHOHCH(CH3)CHO
(3) CH3CH2CHOHCH2CH2CHO
(4) CH3CH2CHOHCH2CH2CHO

TG: @Chalnaayaaar
7. Aldol condensation of acetaldehyde involves the formation of which of the following intermediate
(1) Acetate ion
(2) A carbanion
(3) A carbonium ion
(4) A free radical
8. Aldol condensation will not take place in

(1) HCHO
(2) CH3CH2CHO
(3) CH3CHO
(4) CH3COCH3
dil. KOH
9. ; Product (A) is

O
(1)
(2)
(3)
OH
OH
OH
(4)
10. Acetaldehyde reacts with NaOH/ to form

OH H
(1) CH3—CH2—CH—C=O
OH H
(2) CH3—CH—CH2—C=O
(3) CH3—CH=CH—CHO
(4) CH3—CH2—CH2—C=O
OH H

TG: @Chalnaayaaar
30% H2SO 4 NaOH

11. Predict the product ‘B’ in the sequence of reaction HC  CH ⎯⎯⎯⎯⎯⎯⎯ → A ⎯⎯⎯⎯⎯→B
HgSO4
(1) CH3COONa
(2) CH3COOH
(3) CH3CHO
(4) CH3—CH—CH2CHO
OH
12. In the presence of a dilute base, C6H5CHO and CH3CHO react together to give a product. The product on
further heating gives-
(1) C6H5CH3
(2) C6H5CH2CH2OH
(3) C6H5CH2OH
(4) C6H5CH=CHCHO

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7 8 9 10 11 12
Answer 3 3 1 2 3 2 2 1 2 3 4 4
SOLUTIONS DPP-09
1. --unsaturated aldehyde/ketone is a product of aldol condensation.

 
H3C—C=CH—C—CH3
CH3 O
2. For aldol condensation at least two hydrogen must be present on alpha carbon.
O
' 
CH3—CH2—C—CH3
3. Aldol condensation is given by carbonyl compounds having -H.
4. For aldol condensation at least two alpha hydrogen must be on alpha carbon.
H

CH3—C—C—H
H O
O
5. OH
CH3—C—H + CH3—C—H CH3—CH—CH2—C—H
aldol
O O OH
OH
6. OH
CH3—CH2—C—H CH3—CH2—CH—CH—CHO
aldol
O CH2
O O

OH
7. CH2—C—H CH2—C—H
(carbanion)
H
8. no alpha hydrogen

TG: @Chalnaayaaar
O
O O
O O
9. OH +H2O
+
O OH
   
NaOH 
10. CH3—CHO CH3—CH—CH2—CHO CH3—CH=CH—CHO
OH -Hydroxy carbonyl compound
 
30% H2SO4 NaOH
11. CHCH CH3CHO CH3—CH—CH2—CHO
HgSO4 (Aldol)
(+H2O) OH
(A) (B)
dil   
12. CH3CHO + C6H5CHO C6H5—CH—CH2—CHO C6H5—CH=CH—CHO
NaOH -H2O
(cross aldol) OH
-Hydroxy carbonyl compound

TG: @Chalnaayaaar
1. The major organic product in the following reaction is

O NaOH
(Conc.) H3O+
C6H5—C—CHO
O
(1) C6H5—C—COOH
OH
(2) C6H5—CH—COOH
OH
(3) C6H5—CH—CHO
OH
(4) C6H5—CH—CH2OH
2. Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the
corresponding alcohol and acid?
(1) Benzoic acid
(2) Benzaldehyde
(3) Butanal
(4) Phenol
3. The Cannizzaro reaction is not given by

(1) Trimethylacetaldehye
(2) Accetaldehyde
(3) Benzaldehyde
(4) Formaldehyde
4. Alkanoic acids can be prepared by hydrolysis of

(1) gem-dihalides
(2) 1,1,1–trihaloalkanes
(3) Grignard reagents
(4) Ketones
5. Which of the following compounds will not give benzoic acid with KMnO 4/OHΘ/?
CH3
(1) C6H5—C—CH2OH
CH3
CH3
(2) C6H5—CH
CH3

TG: @Chalnaayaaar
(3) C6H5—CH2—OH
(4) C6H5—CH—COOH
CH3
6. Toluene is oxidised to benzoic acid by-

(1) KMnO4
(2) K2Cr2O7
(3) H2SO4
(4) Both 1 and 2
7. Acids have much higher boiling points than isomeric esters because
(1) Acids form dimers by H–Bonding
(2) Acids are volatile in steam
(3) Esters are non–volatile
(4) Acids can ionise to give protons in aqueous solution
8. Which of the following compounds can form intermolecular H–bonds :-

(1) Ethyl acetate
(2) Methyl formate
(3) Acetamide
(4) Acetic anhydride
9. Which class of compounds shows H-bonding even more than alcohols?

(1) Ketone
(2) Carboxylic acids
(3) Ethers
(4) Aldehydes
10. The correct order of boiling point of following compound is-

(I) CH3CH2CH2CH2OH (II) CH3CH2CH2CHO (III) CH3CH2CH2COOH
(1) I > II > III
(2) III > II > I
(3) III > I > II
(4) I > III > II

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7 8 9 10
Answer 2 2 2 2 1 4 1 3 2 3
SOLUTIONS DPP-10
O OH OH
1. OH H3O
C6H5—C—CHO C6H5—CH—COO C6H5—CH—COOH
self
cannizzaro reaction
2. For undergoing Cannizzaro reaction, Aldehyde must lack any -hydrogen atom.

CHO
No -H
α
3. Acetaldehyde (CH3 − CHO) has -hydrogen
 It does not undergo Cannizzaro reaction.
Cl (i) aqKOH OH
4. R—C Cl R—C OH RCOOH
Cl (ii) H OH
1,1,1-trihaloalkanes Alkaline
hydrolysis
CH2OH COOH
CH3—C—CH3 H3C—C—CH3
KMnO4/OH/
5.
[benzylic H– is absent]
For oxidation of KMnO4/OHΘ/D, benzylic carbon must have atleast one H-atom.
CH3 COOH
KMnO4/OH/
6.
K2Cr2O7/H/
Toluene
O
O H—O
7. 2R—C—OH R—C C—R
O—H O
Dimer
(Intermolecular H-Bonding)

TG: @Chalnaayaaar
O
R
8. R—C—N—H O=C
N—H
H
H
9. Since EN of oxygen atom in acids increases due to -I effect of carbonyl group, strength of H-bonding also
increases.
10. CH3CH2CH2COOH > CH3CH2CH2CH2OH > CH3CH2CH2CHO

(III) (I) (II)
  
Dimer formation due Intermolecular H-bonding
to intermolecular H-bonding is absent
H-bonding

TG: @Chalnaayaaar
1. Acetyl chloride cannot be obtained by treating acetic acid with

(1) CHCl3
(2) SOCl2
(3) PCl3
(4) PCl5
2. What is the product obtained from the following reaction?

O
C—OH
18 H
+ CH3OH
O
C—O—CH3
18
(1) + H2O
O
18
C—O—CH3
18
(2) + H2O
18
O
C—O—CH3
18
(3) + H2O
O
18
C—O—CH3
(4) + H2O
3. Which compound is known as oil of wintergreen?

(1) Phenyl benzoate
(2) Phenyl salicylate
(3) Phenyl acetate
(4) Methyl salicylate

TG: @Chalnaayaaar

4. CH3—CH2—C—OH + NH3
O
(1) CH3—CH2—C—ONH4
(2) CH3—CH2—CN
(3) CH3—CH2—C—NH2
O
(4) CH3—CH2—C—NH3
5. X is heated with soda lime and gives ethane. X is

(1) Ethanoic acid
(2) Methanoic acid
(3) Propanoic acid
(4) Either (1) or (3)
6. Sulphonation of benzoic acid produces mainly-

(1) o-sulphobenzoic acid
(2) m-sulphobenzoic acid
(3) p-sulphobenzoic acid
(4) o- and p-sulphobenzoic acid
NH3 P2O5
7. CH3COOH ⎯⎯⎯⎯ → A ⎯⎯⎯⎯ → B . Identity B.
 
(1) CH4
(2) CH3OH
(3) Acetonitrile
(4) Amonium acetate
8. X is heated with sodalime and gives ethyl amine, X is

(1) Ethanoic acid
(2) Methanoic acid
(3) Propanoic acid
(4) 3-Amino propanoic acid

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7 8
Answer 1 4 4 3 3 2 3 4
SOLUTIONS DPP-11
PCl5
O
PCl3
1. CH3COOH CH3—C—Cl
SOCl2
O O
18
C—OH C—OCH3
18
H
2. + CH3O H + H2O
COOH COOCH3
OH OH
CH3OH/H
3.
Salicyclic acid Methyl salicylate

coil of wintergreen
–H2O
4. CH3—CH2—C—OH + NH3 CH3—CH2—C—O—NH4 CH3—CH2—C—NH2

O O O
(acid) (base)
X NaOH/CaO
 ethane
5. CH3CH2 COO H
–CO2 (C2H6)
(Decarboxylation)
COOH COOH
Con. H2SO4/
6. (–COOH is meta directing group)
SO3H
m-sulphobenzoic acid
O
+NH3 (Base)  P2O5
7. CH3COOH CH3COONH4 CH3—C—NH2

CH3—C N 
(Acid) (Salt)
(A)

TG: @Chalnaayaaar
NaOH/CaO
8. X (C2H5–NH2)

(–CO2)
X = CH2—CH2—COOH
NH2

TG: @Chalnaayaaar
1. Acetic anhydride is obtained from acetyl chloride by the reaction of

(1) P2O5
(2) H2SO4
(3) CH3COONa
(4) CH3COOH
2. What is the major product of the following Reaction

O
C—OH 
C—OH
O
O
C—OH
(1) + CO2
O
C
(2) O + H2O
C
O
OH
(3) + CO2
OH
O
(4)
3. When acyl chloride is heated with Na salt of carboxylic acid, the product is-
(1) An ester
(2) An anhydride
(3) An alkene
(4) An aldehyde
4. The decreasing order of reactivity towards ammonia is-

(1) Anhydrides > Esters > Acid chlorides
(2) Esters > Anhydrides > Acid chlorides
(3) Acid chlorides > Anhydrides > Esters
(4) Anhydrides > Acid chlorides > Esters

TG: @Chalnaayaaar
5. Which one of the following compound gives aspirin on reaching with acetic anhydride in the presence
of H2SO4?
CHO
OH
(1)
COOH
OH
(2)
CHO
COOH
(3)
OH
(4)
NH2
6. CH3COOC2H5 reacts with excess of C2H5MgBr, followed by hydrolysis gives-

(1) CH3—C=O
C2H5
C2H5
(2) CH3—C—OH
C2H5
(3) CH3—C=O
CH3
C2H5
(4) CH3—C=O
CH3
7. Identify the product Y-

CH2—CH2—COO Zn-Hg

Ca X Y
CH2—CH2—COO HCl,
(1) Pentane
(2) Cyclobutane
(3) Cyclopentane
(4) Cyclopentanone

TG: @Chalnaayaaar
Answer Key
Question 1 2 3 4 5 6 7
Answer 3 2 2 3 2 2 3
SOLUTIONS DPP-12
+CH3COONa
1. CH3COCl (CH3CO)2O
(Acetyl chloride) (Acetyl anhydride)
O O
C—O H C

2. –H2O O
C—OH C
O O
(Pthallic acid) (Pthallic anhydride)
3. R—C—Cl +RCOONa (RCO)2O
O
(Acyl chloride) (Acid anhydride)
4. Reactivity of acid derivatives towards NSR is determined by electrophilicity of carbonyl carbon.

R—C—Cl > R—C—O—C—R’ > R—C—OR’
-I +M
O O O O more
+M
less
COOH COOH
OH OCOCH3
5. H /(CH3CO)2O
(H2SO4)
(Salicylic acid) 2-Acetoxy benzoic acid (Aspirin)
Br
C2H5 -Mg C2H5
+C2H5/MgBr OC2H5 C2H5—MgBr
6. CH3—C—OC2H5 CH3—C—OC2H5 CH3—C—C2H5 CH3—C—C2H5
O O–MgBr O OMgBr
+H2O
C2H5
CH3—C—C2H5
OH
3º Alcohol

TG: @Chalnaayaaar
CH2—CH2—C—O  CH2—CH2 Zn–Hg/HCl CH2—CH2

7. Ca C=O CH2
CH2—CH2—C—O –CaCO3 CH2—CH2 +4[4] CH2—CH2
O Cyclopentanone (X) Cyclopentane

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TG: @Chalnaayaaar

Aldehyde, Ketone and Carboxylic Acid Part-01

Aldehyde, Ketone and Carboxylic Acid DPP-01

1. Which reagent below cannot reduce an acid chloride to an aldehyde?

2. Compound which gives only acetone on ozonolysis

5. Catalyst SnCl2/HCl is used in

6 Hydrogenation of benzoyl chloride in the presence of Pd gives

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Aldehyde, Ketone and Carboxylic Acid Part-01

8. In aldehydes and ketones, carbon of carbonyl group is

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Aldehyde, Ketone and Carboxylic Acid Part-01

CH3 OO CH3 CH3 CH3

5. The catalyst SnCl2/HCl is used in Stephen’s reduction.

8. In aldehyde and ketones, the carbonyl group is sp2 hybridised.

  Digital Pvt. Ltd. [3]

Aldehyde, Ketone and Carboxylic Acid Part-02

Aldehyde, Ketone and Carboxylic Acid DPP-02

1. Benzaldehyde as a major product can be prepared by oxidation of toluene by

2. The reagent used in Gattermann-Koch aldehyde synthesis is

3. The oxidation of toluene to benzaldehyde by chromyl chloride is called

4. Which reaction does not give ketone as a major product?

(2) CH3—C— CH3 + aq.KOH

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Aldehyde, Ketone and Carboxylic Acid Part-02

1. CrO3 will oxidise —CH3 into —CHO group.

2. The reagant used in gattermann-Koch aldehyde syntheses is CO + HCl.

3. The oxidation of toluene to benzaldehyde by chromyl chloride is called etard reaction

4. Option (3) is Gattermann Koch Aldehyde synthesis.

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Aldehyde, Ketone and Carboxylic Acid Part-03

Aldehyde, Ketone and Carboxylic Acid DPP-03

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Aldehyde, Ketone and Carboxylic Acid Part-03

4. Product when methyl propanoate reacted with phenyl magnesium bromide?

5. Which have maximum boiling point?

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Aldehyde, Ketone and Carboxylic Acid Part-03

1. 2 R—C—Cl + Cd(R’)2 2 R—C—R’ + 2 CdCl2

2. Ph—C—Cl + CH3MgCl Ph—C—CH3

4. CH3—CH2—C—O—CH3 + PhMgBr CH3—CH2—C—Ph

5. Boiling point  M.W.

  Digital Pvt. Ltd. [3]

Aldehyde, Ketone and Carboxylic Acid Part-04

Aldehyde, Ketone and Carboxylic Acid DPP-04

1. Correct order of reactivity of CH3CHO, C2H5COCH3 and CH3COCH3 is

2. Acetaldehyde reacts with

3. The addition of HCN to carbonyl compounds is an example of

4. Arrange the following compounds in decreasing order of nucleophilic addition reaction:

(I) (II) (III) (IV)

5. Arrange the compounds in order of decreasing reactivity nucleophilic addition reaction:

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Aldehyde, Ketone and Carboxylic Acid Part-04

7. Which gives racemic mixture when reacted with HCN?

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Aldehyde, Ketone and Carboxylic Acid Part-04

2. CH3—C—H can reacts with both electrophile as well as nucleophile.

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Aldehyde, Ketone and Carboxylic Acid Part-04

6. NaCN + HCl ⎯→ NaCN + HCl

7. C—CH3 + HCN C—CH3

  Digital Pvt. Ltd. [4]

Aldehyde, Ketone and Carboxylic Acid Part-05

Aldehyde, Ketone and Carboxylic Acid DPP-05

2. Acetaldehyde reacts with C2H5MgCl the final product is

3. Which gives lactic acid on hydrolysis after reacting with HCN?

4. Identify the product Y in the sequence

5. Which of the following compound does not react with NaHSO3?

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Aldehyde, Ketone and Carboxylic Acid Part-05

5. Ph—C—C6H5 does not react with NaSCO3

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Aldehyde, Ketone and Carboxylic Acid Part-07

Aldehyde, Ketone and Carboxylic Acid DPP-06