CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

CARBONLY COMPOUNDS (ALDEHYDES &

KETONES) CARBOXYLIC ACIDS

EXERCISE-1
PART - II : ONLY ONE OPTION CORRECT TYPE
OBJECTIVE QUESTIONS
PART - 1 : Preparation of Carbonyl Compounds
1. On heating calcium propionate, the product formed is
(A) 3-Pentanone (B) 2-Pentanone
(C) 3-Methyl-2-butanone (D) Propanone
2. A mixed salt of calcium acetate formate on dry distillation gives
(A) ethanal (B) methanal (C) propanone (D) All the three above.
3. Choose the compound whose oxime on hydrolysis yields ethanal –
(A) HCHO (B) CH3CHO
(C) CH3CH2OH (D) CH3COCH3
4. On dipping red hot copper wire in isobutyl alcohol, we get –
(A) An alkene (B) A ketone
(C) An aldehyde (D) None of the above
Pd/ BaSO 4
5. CH3COCl  [H ]
 A
2

The isomers of CH3COCl and A will be respectively –

(A) CH2ClCHO, oxirane (B) Chloral, vinyl alcohol
(C) -chloroethyl alcohol, epoxyethane (D) None of the above
6. Acetic acid when heated (300ºC) with MnO gives
(A) formaldehyde (B) acetaldehyde (C) acetone (D) butaone
7. Ethylidene chloride on treatment with aq. KOH gives
(A) CH3CHO (B) CH2OH.CH2OH (C) HCHO (D) CHO. CHO

PART - 2 : Nucleophilic addition reactions

1. Arrange the following compounds in decreasing orders of rate of exchange of O18 with H2O18

(X) CCl3CHO (Y) CH3CHO (Z) CH3COCH3 (W) CF3CHO

(A) W > Z > X > Y (B) W > X > Y > Z (C) W > Y > Z > X (D) W > Z > Y > X

2. The typical reaction of aldehydes and ketones is

(A) Nucleophilic substitution (B) Nucleophilic addition

(C) Electrophilic substitution (D) Electrophilic addition

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
3. Acetaldehyde on reaction with sodium hydrogen sulphite produces

(A) (B)

(C) (D)

4. What would be the product when carbonyl compound reacts with HCN -

(A) Cyanohydrin (B) Hydroxy acid

(C) Hydroxy amide (D)Amino alcohol

5. Write the product of following reaction :

   Product
NH2 NH2

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

6. Which of the following is most reactive towards nucleophilic addition reactions ?

(A) CH3COCH3 (B) CH3CH2COCH2CH3
(C) Ph– –CH3 (D) Ph– –Ph

O16
|| D2O18
7. CH3  C  H  
D

Given the following reaction intermediate is :

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

8. Aldehyde with NH2–NH2 forms :

(A) hydrazones (B) aniline (C) nitrobenzene (D) none of these

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

PART - 3 : Condensation reactions

1. (X) is the product of cross aldol condensation between benzaldehyde (C6H5CHO) and
acetone. What is its structure ?

(A) (B) C6H5–CH=C–(CH3)2

(C) C6H5–CO–CH2–C=(CH3)2 (D) None of these
2. CH3– –CHO 
dil.NaOH
 Product, The product of this reaction would be :-

(A) (B)

(C) (D)

3. What is the principal product of the follwoing reaction ?

Product

(A) (B) (C) (D) None of these

PART - 4 : Cannizzaro's reactions

NaOH
1. In the reaction, (CH3)3CCHO + HCHO  
 A + B.
heat

the products (A) and (B) are respectively :

(A) (CH3)3CCH2OH and HCOO– Na+. (B) (CH3)3CCOONa and CH3OH.
(C) (CH3)3CCH2OH and CH3OH. (D) (CH3)3COONa and HCOO– Na+.
2. In Cannizzaro reaction-
(A) Aldehyde is converted into alcohol
(B) Alcohol is converted into aldehyde
(C) Primary amine is converted into isocyanide
(D) Acid is converted into amine
3. For Cannizzaro's reaction, which is necessary-
(A) Presence of  –C (B) Absence of  –C
(C) Presence of  –H (D) Absence of  –H

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

KOH
4. + HCHO  (A) + (B)

The product (A) and (B) are respectively :

(A) (B) + CH3OH

(C) (D) Both (A) and (B),

5. Phenylglyoxal, C6H5COCHO, on heating with concentrated NaOH gives

(A) C6H5COONa and CH3OH (B) C6H5CH2OH and HCOONa
(C) C6H5CHOHCOONa (D) C6H5COONa and HCOONa
6. In the cannizzaro's reaction the intermediate that will be the best hydride donor ?

(A) (B)

(C) (D)


OH
7. In the Cannizzaro reaction : 2PhCHO  PhCH2OH + PhCOO– the slowest step is
(A) The attack of OH– at the carboxyl group
(B) The transfer of hydride to the carbonyl group
(C) The abstraction of proton from the carboxylic acid
(D) The deprotonation of PhCH2OH

8. In the given reaction Product is

(A) (B)

(C) (D)

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
PART - 5 : Redox reactions
O
||
Ph – CHOLiAlH 4
1.   
    [X], Product (X) in this reaction is :

OH / 

(A) (B)

(C) (D)

2. 

Above conversion can be achieved by

(A) NH2–NH2/ NaOH (B) Zn–Hg/HCl (C) LiAlH4 (D) NaBH4.

PART - 6 : -Halogenation, haloform, -deuteration reactions


1. 2  Major Product is :
Br / H

(A) (B)

(C) (D) Both A and C

2. Consider the given reaction :

O O
|| C6 H5COOOH ||
CH 3  C  CH 3      CH  C  O  CH 3
 3

The above reaction is known as :

(A) Baeyer-villiger oxidation (B) Oppenaur oxidation
(C) Periodate oxidation (D) Peroxide oxidation

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
3. In which of the following reaction deuterium exchange is not observed ?

D O / OH
(A) 2  

excess


D O / OH
(B) 2  


 
D O / OH D O / OH
(C) 2  
 (D) 2  


4. Which will give silver mirror test with Tollens reagent :

(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D) All of these

PART - 7 : Carboxylic acid (Preparation Methods)

1. In the following reaction final product is :

H
C6H5 MgBr + CO2   
 Find product
Ether

(A) Benzoic acid (B) Benzaldehyde (C) Benzamide (D) Benzene
2. In the reaction sequence :

CH MgBr (i ) CO
CH3–CC–H 3  CH4+ (A)  
2  (B)

(B) will be:
( ii ) H 2O / H

(A) CH3–CC–CH3 (B) CH3–CC–MgBr

(C) CH3–CC–COOH (D) CH3–CH=CH–COOH
3. Which of the following does not give benzoic acid salt on oxidation with hot alkaline KMnO4.
(A) Ph–CH3 (B) Ph–CH=CH–CH3 (C) Ph–CC–CH3 (D) Ph–C(CH3)3
4. The acid D obtained through the following sequence of reactions is

H O
Alc . KOH
C2H5Br 
Br2
 A  B  C 3  D
KCN
CCl4 ( excess )

(A) Succinic acid (B) Malonic acid (C) Maleic acid (D) Oxalic acid
5. In the reaction sequence :
O
|| HCN H 2O / H 
CH 3  C  H 
 (A)   Product, Product will be:
OH 

OH OH
| |
(A) CH 3  C  COOH (B) HOOC  C  CH 3
| |
H H
OH OH OH
| | |
(C) Mixture of CH 3  C  COOH and HOOC  C  CH 3 (D) CH 3  CH  CONH 2
| |
H H

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
6. In which of the following reaction the final product is neither an acid nor an acid salt.

Tollen's reagent KMnO / O H
(B) CH3 –CH2–OH 
4
(A) Ph–CHO 
Fehling solution 
K Cr O / H
(C) Ph–CHO  (D) Ph–CH2–OH 2 27 
7. In the given reaction :

O
|| ( i ) Br2 / KOH
C6 H 5  C  CH 3    CHBr3 + [X], [X] will be:

( ii ) H
(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH
8. The acid D obtained through the following sequence of reactions is -
Alc.KOH Br KCN H O

C2H5Br  A2
CCl
B  C 
3

4 (excess)

(A) Succinic acid (B) Malonic acid (C) Maleic acid (D) Oxalic acid

PART - 8 : Carboxylic acid (Chemical Properties)

1. Formic acid can be distinguish from acetic acid because formic acid :
(A) release H2 with sodium (B) gives ester with alcohol
(C) reduces ammonical AgNO3 (D) turns red litmus to blue
2. Consider the given reaction :
Br / 
RCOOAg 2  R–Br
which one of the following acid will give maximum yield of R–Br in the above reaction?
(A) CH  CH  COOH (B) CH3–CH2–CH2–COOH
3
|
CH 3

CH 3
|
(C) CH 3  C  COOH (D) All will give same yield
|
CH 3
3. Sodium bicarbonate reacts with salicylic acid to form:

(A) C6H5ONa (B) (C) (D)

4. Which of the following will not undergo Hell-Volhard Zelinsky (HVZ) reaction ?
(A) HCOOH (B) CH3COOH (C) CH3CH2COOH (D) CH3CHBrCOOH.
Re d P  Br2
5. CH3–CH2–CH2–COOH   CH3  CH2  CH  COOH
|
Br

This reaction is called

(A) Cannizzaro reaction (B) Aldol condensation reaction
(C) Hell Volhard Zelinsky reaction (D) Reimer tiemann reaction

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
6. Which of the following will undergoes decarboxylation on heating?
(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D) Glutaric acid
7. Which of the following is the weakest acid ?
(A) Cl3CCOOH (B) Cl2CHCOOH (C) ClCH2COOH (D) CH3COOH
8. What product is formed when acetic acid heated with P2O5 .
(A) Acetyl chloride (B) Acetate ester
(C) Acetic anhydride (D) Acetaldehyde
9. Which of the following will not yield a cyclic compound on heating :

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

10. The reaction : RCOOAg + Br2 CCl4 ,Reflux

   R–Br +AgBr + CO2
is called
(A) Wurtz reaction (B) Hunsdiecker reaction
(C) Friedel-Crafts reaction (D) Kolbe's reaction
11. RCOOH  RCH2COOH. This conversion is known as reaction :
(A) Arndt-Eistert reaction (B) Hunsdicker reaction
(C) HVZ reaction (D) Cannizaro reaction

PART - 9 : Acid Derivatives (Acid Halide, Ester, Anhydride & Amide)

1. Acetic anhydride is prepared in the laboratory by heating sodium acetate with

(A) ethyl chloride (B) acetyl chloride

(C) conc. H2SO4 (D) zinc dust

2. A fruity smell is produced by the reaction of C2H5OH with :

(A) CH3COCH3 (B) CH3COOH (C) PCl5 (D) CH3CHO

3. Kolbe’s electrolysis of aqueous potassium ethanoate leads to the formation of -

(A) Ethene (B) Methane (C) Ethane (D) Ethyne

4. A compound with molecular formula C4H10O4 on acylation with acetic anhydride gives a compound
with molecular formula C12H18O8. How many hydroxyl groups are present in the compound ?

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

5. Benzoyl chloride on treatment with ammonia gives

(A) Benzamide (B) Acetamide (C) Benzylamine (D) Benzoic acid

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

EXERCISE-2
PART - I : ONLY ONE OPTION CORRECT TYPE

ALDEHYDES & KETONES

1. Which of the following compound can not be formed in given aldol condensation reaction :

CH3 CHO  CH3 COCH3 

Dil.NaOH



(A) CH3 – CH = CH – CHO (B) CH3 – C  CH – CHO

|
CH3

(C) CH3 – C  CH – C – CH3 (D) CH3 – CH2 – CH  CH – CHO

| ||
CH3 O

2. Major product, Major product is :

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

3. Which of the following can show Aldol condensation reaction :

H–C–D
(A) (B) (C) (D) ||
O

4. Consider the following sequence of reactions :

Heat H SO 4
+ H2NOH  A 2 
 B.
Heat

The products (A) and (B) are, respectively :

(A) and (B) and

(C) and (D) and

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
5. In the given reaction sequence B is

(A) (B)

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

6. (A) (B)

The reactant (A) will be :

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

O CH3
|| | KOH, H2O
7. CH3 CCH2CCHO     Product (C H O) :
 7 10
|
CH3

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

8. + Product

(A) (B)

(C) (D)

9. The suitable reagent for the following reaction is :

(A) LiAlH4 (B) Na / C2H5OH (C) H2 / Ni (D) CH2 = O /

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
10. Which of the following can be the product/s of following reaction.

Conc. NaOH
    


(A) I, II, IV (B) III, IV (C) II, V (D) I, V

(i ) CH ( COOC H ) / Pyridine
11.  2  2  5 2
 
 (P) is
(ii) H O, 
2

(A) (B)

(C) (D)

12. (mixture of alkenes) (mixture of carbonyl compounds)

The incorrect statement is

(A) Total five alknes are obtained.
(B) Total six different carbonyl compounds are obtained on ozonolysis.
(C) All carbonyl compounds can give aldol reaction when treated with dil KOH.
(D) Only two carbonyl compounds give positive iodoform test.

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
13. What is the final product of this sequence of reactions ?

Product

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

14. Ph–CH2–COOEt + (A) (B)

Product B is :
(A) Ph–CH2–COOH (B) Ph–CH2–COOEt

(C) (D) None of these

15. + (C6H5)3P = CHCH3  Product

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

16. In the following reaction, A + B

A and B respectively are :

(A) + CH3COOC2H5 (B) + CH3– C – OC2H5

||
O

(C) + C2H5O– C –OC2H5 (D) + C2H5O– C –CH2– C –OC2H5

|| || ||
O O O

17. Aromatic carbonyl compounds having molecular formula C8H8O react with NH2OH how many
oximes can be formed :
(A) 8 (B) 10 (C) 12 (D) 6

O
Ph ||
C6H5 Br / CH COOH
18. 
2 3
 Products with stereochemical relation
CH3

(A) Enantionmer (B) Diastereomer (C) Structural isomer (D) Identical

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

CARBOXYLIC ACID & DERIVATIVES

19. Which of the following does not give benzoic acid on hydrolysis ?
(A) Phenyl cyanide (B) Benzoyl chloride (C) Benzyl chloride (D) Methyl benzoate
20. Identify the final product in the following sequence of reaction.

SOCl NH PO
 
2
 
3
  
2 5

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

CH NH
21.  
3

2
 X, X is
heat

(A) (B)

(C) (D)

22. CH3CH2CH2CONH2 is boiled with aqueous NaOH, then the reaction mixture is acidified with HCl.
The products obtained are
(A) CH3CH2CH2COO– + NH3 (B) CH3CH2CH2COONa + NH3
(C) CH3CH2CH2COOH + NH4Cl (D) CH3CH2CH2COO– + NH4Cl.
23. In how many steps decarboxylation reaction is taking place.

H O  
 2 / OH KMnO  NaOH / CaO / 
3 
     
4       

Step 1 Step 2 Step 3 Step  4 Step 5 Step  6

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

PART - II : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. Observe the following reaction Products.

The correct statement is

(A) The product is a mixture of two compounds
(B) The product is optically inactive
(C) The product is a mixture of two chiral and one achiral stereoisomer
(D) The product is a mixture of three stereoisomers.
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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
2. In the given reaction which one of the following statement is correct –

(A) Oxime may be E/Z.

(B) Amide on hydrolysis gives a mixture acetic acid, benzoic acid, Aniline and methylamine.
(C) Preparation of oxime is nucleophilic addition followed by elimination reaction.
(D) Oxime and amides are isomers.
3. Base catalysed aldol condensation occurs with :
(A) Benzaldehyde (B) Propanal (C) Propenal (D) Acetophenone
4. The correct statements about following reaction are :

PhCH  O  CH2  O 
OH
(P  Q)  (R  S)
(major) (minor)

(A) R, S arePhCOO  ,HCOO  (B) R, Q are PhCOO ,CH3 OH

(C) P or Qcan beHCOO (D) R or S can be PhCOO

5. Which of the following will give 3-pentanone.

 (1) CH3 – CH2 – MgBr

(A) (CH3 – CH2COO )2 Ca  (B) CH3 – CH2 – C  N    


( 2 ) H3 O

O O
|| || (1) H O / H
(C) CH3 – C – CH2 – CH2 – C – OC 2H 5  2    (D)
( 2 ) NaOH( cao )



6. In which reaction product is hydrocarbon?

(i)
(A)   Br2 / CCl 4
(B) CH3COOAg   
(ii) ZnHg / HCl

CH3
NaOH | C 2 H 5OH
(C) Ph–COOH  (D) CH3 – C – Cl  
CaO, 
|
CH3

7. Which of them liberate a gas which turns lime water milky.

O
COOH
(A)  
(B) CH 3 – CH – COOH 

|
COOH

COOH
Ca(OH)2 /  
(C) HOOC–(CH2)5–COOH   (D) 
COOH

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
8. Identify the product P in the given reaction :

+ + -
SOCl2 N2O5 (CH3)2CuLi Fe / H NaNO2 / H PhOH / OH
X Y Z

NO2 NH2

(A) X is (B) Y is
C O C O

CH3 CH3

(C) Z is N N C CH3 (D) Z is N N OH

OH C O
CH3

PART - III : COMPREHENSION & MATCH THE COLUMN

Comprehension # 1
Aldehydes and Ketones reacts with NH2OH to form Aldoximes and Ketoximes respectively.
Configuration of these can be determined by Beckmann rearrangement as that group migrates
which is anti w.r.t –OH.
R R H2O
 R' C  N  R 
..

 R'C  N  R
..

C N C N (II )  ( III )
R'C  NH  R
OH OH2 | ||
R' R'
OH O

H SO4 H O
1. [X] 2   2 Ph – NH2 +

Identify the configuration of [X] compound :

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

2. Which step is Rate determening step ?

(A) I (B) II (C) III (D) IV

NH2OH (1) H SO
3.  (A)    (B).
2 4
 
( 2) hydrolysis

The product (B) is :

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

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
Comprehension # 2
Carbonyl compound which contains –H gives aldol condenation reaction in presence of alkaline
medium. The reaction between two molecules of acetaldehyde take place as follows in presence
of base.

4. Aldol condensation reaction is given by

(A) C6H5–CHO (B) CX3 – CHO

(C) O2N CHO (D) C6H5–CH2–CHO

5. + Product

(A) Ph – CH = CH – (CH2)5 – CHO (B) Ph – (CH2)5 – CH = CH – CHO

(C) (D)

6. Intramolecular aldol condensation reaction is given by

(A) 2,5-diketone (B) 2,7-diketone
(C) 2,6 and 2,8-diketone (D) All of these
Comprehension # 3
The conversion of aldehyde having no alpha hydrogen to a mixture of carboxylic acid and primary
alcohol is known as cannizzaro reaction. The most important feature of this reaction is the
conjugate base of hydrate of aldehyde.

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
7. Which step is rate determining step
(A) step I (B) step II (C) step III (D) step I and II both
8. In the given reaction final product is

Product is :

(A) CH3OH + (B) HCOONa +

(C) HCOONa + (D) HCOONa +

Comprehension # 4

Study following mechanism of haloform reaction.

X X
H
| - |
|
R  C  C  H (1) HO, (2) X2 RCC X
R  C  C  H + HO - a || | C || |
|| |
O H O H
O H

X
- | - d
- HO (1) HO
f
CHX3  + R – C – O  R  C  OH + -CX R C C X
|| 3 e || | (2) X2
||
O O O X

9. Which step is RDS

(A) a (B) b (C) c (D) f

10. Which of the following compounds gives haloform reaction ?

(A) CH3  C  CH2  C  CH3 (B) CH3  C  CH2  NO 2

|| || ||
O O O

O
C – CH3
(C) CH3 – C – CH2 – CH2 – C (D)
|| ||
O O
O O

11. Which step produces most acidic compound

(A) a (B) c (C) d (D) b

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
12. Column-I Column-II
Aldol product Reactant required

(A) (p)

(B) (q) HCHO

(C) (r) Ph–CHO

(D) Ph–CH=CH–CHO (s) CH3–CHO

13. Match the column
Column-I Column-II

(A) (p) Hydrolysis

(B) (q) Esterification

(C) (r) Saponification

(D) (s) Acid base reaction

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

EXERCISE-3
SINGLE AND DOUBLE VALUE INTEGER TYPE
1. How many reactions will produce carboxylic acid, as their end product.


AlCl3 I2 / OH
(1) + CH3– –Cl   
 (2) HI
   H3 O
  
NaCN


H

(3) Alc . KOH /  O (4) KMnO

 
    3
  
4

H2O /  

CH Cl Cl2 / h NaOH H Cl2 Mg

CO 2
(5)  
3
       (6)   
  
AlCl3 excess excess AlCl3 THF, H

2. An organic compound (A) consists of C, H and O gives a characteristic colour with ceric
ammonium nitrate. Treatment of (A) with PCl5 gives (B) which reacts with KCN to from (C). The

reduction of (C) with Na/C2H5OH produces (D) which on heating gives piperidine with

the evolution of ammonia. Identify. The number of carbon atoms in compound D is x and the
number of carbon atoms in compound A is y, what is the value of x + y ?

14
(1) SOCl CH N Ag O H O/ NaOH(CaO)
3.   
2
   
2 2 2
 2        Product
excess excess excess excess

How many C14 atoms are present in the product.

4. Number of possible intra molecular aldol condensation products on heating with NaOH.

5. 
HCN
 D 
H3 O

E

Then (E–B) = ?
6. Total aldol condensation products (including stereoisomers) formed by the reaction between
acetaldehyde and acetophenone is :
7. How many of the following will form stable hydrate :

(1) CH3CHO (2) CCl3CHO (3) CF3CHO (4)

(5) (6) (7) (8)

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

RANKER’S PROBLEMS
PART - I : OBJECTIVE QUESTIONS

1. Which of the following is correct order of esterification of following acids with CH3OH :
HCOOH , CH3 COOH , CH3 – CH2 – COOH ,

I II III IV

(A) I = II = III = IV (B) I > II > III > IV (C) I < II < III < IV (D) I > IV > III > II

2. Identify final product in the following reaction


 product.

(A) (B) CH2= CH–COOH (C) (D) CH3–CH2–OH

3. Which of the following reaction represents incorrect product.

 
(A)  (B)  + H2O

(C) 
 CH3COOH + CO2  (D) 
 CH2=CH–COOH + CO2

4. (A) would be :

(A) CH3  C  O  C  CH3 (B) CH3–COOH (C) CH3–COCl (D) CH3–CONH2

|| ||
O O

 NH NaOH Br KOH HCl

5.  (A) 
3  (C) 2 (D)  (E)
(B)  
H2O

In this reaction the product (E) is :

(A) o-nitrobenzoic acid (B) Salicylic acid (C) anthranilic acid (D) Crotonic acid

CH2 — CONH2 P2O5 H3O
6. |   (P) 
  (Q)

CH2 — CONH2
The product (Q) is

CH2 — COOH
(A) CH3–CH2–COOH (B) | (C) (D) CH3–COOH
CH2 — COOH

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

O
||
LiAlH4
7. C 2H5 O  C  (CH2 )2  CN ( excess
   X, X is
)

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

P O MeMgBr Ca ( OH)2 ,I2

8. 4 10
 P   

 Q     R, compound R is
 H3 O

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


9. H O
 [X]
3 


Select the correct statement.

(A) X gives effervescence of CO2 with NaHCO3
(B) X will produce alkane when treated with Zn-Hg/HCl
(C) X will produce symmetrical diketone when treated with sodalime
(D) All of these

More than one choice type

10. In which of the following reactions correct major product is mentioned ?

(A) +

(B) + H SO
2
4

1. OH
(C)   +
2 . H

(D) + H2SO 4
 

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

PART - II : SUBJECTIVE QUESTIONS

1. Give the product of each of the following reactions :

(CH CO2 )O
MeCH(CH2COOH)2 3   F..

2. Both cis- and trans-1,2-cyclohexanedicarboxylic acids form anhydrides on heating, but the
anhydride formed from the cis-1,2-cyclopentanedicarboxylic acid only. explain.

3. 30 g of monobasic carboxylic acid A consumed 0.5 moles of NaOH for its neutralisation. A is
subjected to following treatments :

Cl2 / P  Monochloro  Esterification Hydrolysis

KCN (alc.) [B]    
[A]    derivative        (Ester)      Dicarboxylic acid [C]
  Acid
with C2H5OH

Heat
 
 A
150 º C

Give structures of A, B, C providing the sequence of reactions.

Pyridine
4. + 
 X, X is

5. In the given reaction sequence (A) (B)

(A) and (B) respectively are :

6. An acidic compound (A), C4H8O3 looses its optical activity on strong heating yielding (B), C4H6O2
which reacts readily with KMnO4 and decolourises it. (B) forms a derivative (C) with SOCl2 which
on reaction with (CH3)2 NH gives (D). The compound (A) also forms unstable compound (E) on
treatment with dilute chromic acid. (E) decarboxylate readily to give (F) C3H6O which on treatment
with amlgumated zinc and HCl gives hydrocarbon (G). Give structures of (A) to (G).

7. How many compounds out of the following are more reactive than ethyl acetate towards hydrolysis.

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

(VI) (VII) (VIII) (IX) (X)

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS
8. Complete the folliowing reaction
(a) Toluene + phthalic anhydride + AlCl3
(b) Product from (a) + Conc. H2SO4 + 
9. Complete the following by reactions. Find the unknown A to F :

[A] C H6
CH4  CH3Br 6 [C]
 [B]  OH [D]
AlCl3 (anhyd.) 


10. The number of isomeric products formed in the following reaction is :

Acetic anhydride / Sodium acetate / heating

         

11. Explain briefly the formation of the products giving the structures of the intermediates.

O
||
i. OH ¯ / 
  H3 C  CH  C  OH
ii. H
|
CH2  C  OH
||
O

(1) SOCl2
( 2) NH3
( 3) Br2 / KOH /  (1) dil. NaOH / 
( 4) aq.NaNO2 / HCl ( 2) PhMgBr
( 5) Cu /  ( 3 ) H
12. CH3—CH2—COOH    ( X)      ( Y)
(C 2H4 O) (C10H12O)

( 2 ) PhMgBr
H SO / 
2 
4  (Z)     
(3 ) H
(C16H16O)

13. + AlCl
 

3


The products can be :

14. The respective boiling points and molecular weights (in/gmol) of the following amides are :
MeCONH2, 221ºC and 59; MeCONHMe, 204ºC and 73 ; MeCONMe2, 165ºC and 87. Explain.
15. In the following ester there are three carbon oxygen bonds denoted by x, y and z. Then bond
length of (i) x, y (ii) y, z and (iii) x, z orders are :

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

ANSWERS
EXERCISE - 1
PART - 1
1. (A) 2. (A) 3. (B) 4. (C) 5. (A)
6. (C) 7. (A)

PART - 2
1. (B) 2. (B) 3. (D) 4. (A) 5. (A)
6. (A) 7. (B) 8. (A)

PART - 3
1. (A) 2. (A) 3. (A)

PART - 4
1. (A) 2. (A) 3. (D) 4. (A) 5. (C)
6. (C) 7. (B) 8. (B)

PART - 5
1. (A) 2. (B)

PART - 6
1. (D) 2. (A) 3. (A) 4. (D)

PART - 7
1. (A) 2. (C) 3. (D) 4. (A) 5. (C)
6. (C) 7. (B) 8. (A)

PART - 8
1. (C) 2. (B) 3. (B) 4. (A) 5. (C)
6. (C) 7. (D) 8. (C) 9. (A) 10. (B)
11. (A)

PART - 9
1. (B) 2. (B) 3. (C) 4. (D) 5. (A)

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

EXERCISE - 2
PART - I
1. (D) 2. (B) 3. (A) 4. (D) 5. (B)
6. (B) 7. (C) 8. (A) 9. (D) 10. (C)
11. (A) 12. (D) 13. (B) 14. (A) 15. (B)
16. (C) 17. (B) 18. (B) 19. (C) 20. (C)
21. (C) 22. (C) 23. (C)

PART - II
1. (BCD) 2. (ABCD) 3. (BD) 4. (CD) 5. (ABD)
6. (AC) 7. (ABC) 8. (ABD)

PART - III
1. (A) 2. (B) 3. (A) 4. (D) 5. (D)
6. (D) 7. (B) 8. (C) 9. (A) 10. (C)
11. (B)
12. (A - p,q) ; (B - p,r) ; (C - q,s) ; (D - r,s)
13. (A - s) ; (B - q, s) ; (C - p, s) ; (D - p, r, s)

EXERCISE-3
1. 5(1, 2, 3, 5,6) 2. 5+3=8 3. 2 4. 3

5. The structure of E is and B is

so, (E – B) = (116 – 106) = 10

Ph–CH=CH–CH3 
O3

 
Aldol
 
HCN

KOH
(A)



H O
 

3

6. 8
7. 5 (2,3,4,5,6)

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

RANKER'S PROBLEMS
PART - I

1. (B) 2. (A) 3. (D) 4. (B) 5. (C) 6. (C) 7. (D)

8. (B) 9. (B) 10. (ABCD)

PART - II

1. F=

2. The anhydride formed from the trans-dicarboxylic acid must have a trans fusion of two rings.
There is too much strain while both ring are five -membered.

3. (A) = CH3COOH ; (B) = ; (C) =

4. X=

5. (A) = (B) =

6. (A) ; (B)

(C) ; (D)

(E) ; (F) ; (G)

7. 6(I, II, III, V, VII & X)

8. (a) + AlCl


3

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 CARBONYL COMPOUNDS (ALDEHYDES & KETONES) & CARBOXYLIC ACIDS

(b) conc.H SO
  
2 
4


9. [A] Br2 /h [B] [C] Cl2 (g)/h [D]

[E] [F] NH2OH/H+

10. 2
11. First, anion of Malonic ester is formed which attacks as a nucleophile on the other reagent.
(1) SOCl2
( 2) NH3
(3 ) Br2 / KOH /  O
( 4 ) aq.NaNO2 / HCl O
(5 ) Cu / 
|| dil. NaOH /  ||
12. CH3—CH2—COOH      CH3 — C — H  CH3 — CH  CH — C — H
( X)

O OH
|| (CH3 )2 CO |
CH3 — CH  CH — C — Ph    CH3 — CH  CH — CH — Ph
Al ( tBuO )3 /  ( Y)

O
|| H
CH3 — CH — CH2 — C — Ph 
|
Ph
( Z)

H



13. , ,

14. Dimethylacetamide lacks a H on N for intermolecular H-bonding; thus its bp is lowest, its highest
molecular weights notwithstanding. Acetamide has two H's and is extensively H - bonded resulting
in the highest bp, while methylacetamide has only one H and less H-bonding.
15. (I) x < y (II) y < z (III) x < z

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