Chemistry : Aldehydes and Ketones

ASSIGNMENTS

SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Identify missing compounds in the following
O
O
O
H O
H
+ A  B


2. Identify the products

O
||
CH N Ag O HO
CH3  C Cl 
2 2
 A 
2
 B 
2
C
3. Identify the products :

CO2Et
 H3O 
Zn / Hg
OEt
 X   Y   Z
 HCl
N

CH2CO2Et
4. Identify the organic products in the following reactions.
O
O
PhCO3H H B 
(i)     A 
CHCl3 H2O

5. An organic compound A reacts with MeMgI to form an addition product which on hydrolysis forms the
compound B. Compound B gives blue colour salt in victor meyer’s test. Determine compounds A and
B.
6. A compound is soluble in concentrate H2SO4, it does not decolourise bromine in CCl4 but is oxidised by
chromic anhyride in aqueous H2SO4 within 2 seconds, turning orange solution to blue, green and then
opaque. Which is the original compound?
7. Evaluate the following –
I2 Ag H 2SO 4
CH 3  CO  CH 3 
alkali
 A 

B 
Hg 2
C

8. An organic compound contains C = 40%, H = 6.7% and O = 53%. Its V.D. is 15. It reduces Fehling’s
solution. Determine the organic compound.
 Chemistry : Aldehydes and Ketones

9. Give complete mechanistic approach for the following reaction.

CHO
CH 3COONa
 (CH 3CO)2 
H O
?
3

OH
10. Give product and detailed mechanism how it is formed?

O O

OH
OMe C C  ?

LEVEL - II
1. The reaction of H2NOH with a symmetrical ketone R2C=O, gives one oxime, but two isomeric oximes
may form from the reaction of an aldehyde or a nonsymmetrical ketone. Explain and illustrate with
structures.
2. Cyclohexanone semicarbazone precipitates from a solution containing one equivalent each of
cyclohexanone and benzaldehyde when one equivalent of semicarbazide is added. After standing for a
few hours, the only product is benzaldehyde semicarbazone. Explain.
3. Compound (A)C8H8O is water insoluble and gives yellow precipitate with I2/NaOH. It reacts with
NH2OH in presence of NH4Cl/NH4OH to give two geometrical isomers (B) and (C) having molecular
formula C8H9O. These two compounds donot undergo dehydration. What will be structure of (A), (B)
and (C)?
4. Convert 2-cyclohexenone into the following compounds :

O CH2

(a) (b)

CH3

OH
H3C OH

(c) (d)

5. Show which amine and carboxyl compound combine to give the given enamine.

N
Chemistry : Aldehydes and Ketones

6. Predict the major product ?

CH
C

1. HgSO 4 , H 3O

2. NH OH
?
2

7. Identify (A), (B), (C), (D) and (E) in the following schemes and write their structures :

Br2 / CCl4 NaNH2 HgSO 4 / H2SO4

  (A)   (B)   (C)

NH 2 NHCONH2
(C)   (D)
NH 2 NHCONH 2
(D)   (E)

8. A hydrocarbon (A), C7H12O on ozonolysis gives a compound (B) which undergoes aldol condensation
giving 1–acetylcyclopentene. Identify (A) and (B).
9. What are the final products of the following aldol condensations ?
O

OH , 
CHO + C CH3   (A)


OH , 
O   (B)

10. Which of the following will give yellow precipitate with I2 / NaOH and show how?
(i) ICH2COCH2CH3 (ii) CH3COOCOCH3
(iii) CH3CONH2 (iv) CH3CH(OH)CH2CH3

LEVEL - III
1. Compound (A), C8H8 on treatment with NH2OH HCl gives (B) and (C), (B) and (C) rearrange to give
(D) and (E), respectively, on treatment with acid. (B), (C), (D) and (E) are all isomers of molecular
formula C8H9NO. When (D) is boiled with alcoholic KOH, and oil (F), C6H7N separates out. (F) reacts
rapidly with CH3COCl to give back (D). On the other hand, (E) on boiling with alkali followed by
acidification gives a white solid (G), C7H6O2. Identify the compounds (A), (B), (C), (D), (E), (F)
and (G).
2. A compound (A), C5H10O, does not react with cold, aqueous KMnO4 and does not add bromine. When
(A) is reduced, (B) C5H10O is formed. Treatment of (B) with hot 20% sulphuric acid yields (C), C5H10O.
Compound (C) instantly adds bromine and decolouries aqueous KMnO4 . When (C) is dissolved in cold
70% H2SO4 and the resulting solution diluted with water compound (D), C5H15O is formed. Although
(B) can be reoxidised to (A), similar oxidation of (D) to a five–carbon–atom compound cannot be
accomplished. Assign the structures of compound (A), (B), (C) and (D).
 Chemistry : Aldehydes and Ketones

3. A compound has two isomers (A) and (B) of formula C5H10O. Isomer (A) on treating with NaOH(aq)
gives 2,2–dimethylpropan–1–o1 and 2,2–dimethylpropanoic acid salt. The isomer (B) on treating with
NaOH(aq) gives 3–hydroxy–2–propylheptanal. What are compound (A) and (B) ?
4. A compound (A) (C11H22) when ozonised yield (B) (C6H12O) and (C) (C5H10O). Mild oxidation of (C)
yeild (D) C5H10O2. Compound (B) reacts with NaOCl to yeild chloroform and sodium salt of (D).
Reduction of (B) with LiAlH4 yield (E) (C6H14O). Dehydration of (E) gives (F) (C6H12). Ozonolysis of
(F) yields (G) (C2H4O) and (H) (C4H8O). Compound (H) does not react with Tollen’s reagent or
Fehling’s solution but does form an oxime and semicarbazone. Write these reactions using structural
formula throughout and identify the compounds (A), (B), (C), (D), (E), (F), (G) and (H).
5. Unknown (K), C5H10O, rapidly decolourised a solution of bromine in carbon tetrachloride. When (K)
was dissolved in cold concentrated H2SO4 and then heated with water, (L) resulted. (L), C5H12O,
reacted with dichromic acid H2Cr2O7 to give (M), C5H10O. Both (L) and (M) gave positive idoform
tests. The iodoform reaction mixture also yielded isobutyric acid (CH3)2CHCOOH. What are the
structures of compounds (K), (L) and (M) ?
6. An organic compound (A) gives positive liebermann’s reaction and on treatment with
CHCl3/KOH followed by hydrolysis gives (B) and (C). Compound (B) gives colour with Schiff’s reagent
but (C), which is steam volatile, on treatment with LiAlH4 gives (D), C7H8O2 which on oxidation gives
(E). Compound (E) reacts with (CH3CO)2O / CH3COOH to give a pain reliever (F). Give structures of
compounds (A), (B), (C), (D), (E) and (F) with proper reasoning.
7. A organic compound (A) of molecular weight 140.5 has 68.32% C, 6.4% H and 25.26% of chlorine.
Hydrolysis of (A) with dil. acid gives a compound (B), C8H10O . Compound (B) can be oxidised under
mild conditions to compound (C), C8H8O . Compound (C) form a phenyl hydrazone (D) with phenyl
hydrazine and gives a positive iodoform test. Deduce the structure of compouds (A), (B), (C) and (D)
with proper reasoning.
8. Compound (A), C8H8O can be oxidized with KMnO4 to (B), C8H6O4 . Compound (B) is a dicarboxylic
acid, but does not form anhydride on heating. (B) when treated with bromine in presence of Fe, gives
only one monobromo derivative (C), C8H5BrO4 . Give the structural formula of (A), (B), (C) and (D).
9. An alkene (A) on ozonolysis yields acetone and an aldehyde. The aldehyde is easily oxidised to an acid
(B). When (B) is treated with bromine in presence of phosporus, it yields a compound (C) which on
hydrolysis gives a hydroxy acid (D). This acid can be obtained from acetone by the reaction with HCN
followed by hydrolysis. Identify compound (A), (B), (C) and (D).
10. An organic compound (A) C5H8O adds Br2 to give C5H8Br2O. It does not react with Tollen’s reagent
but enters into reaction with phenyl hydrazine. Ozonolysis of (A) gives acetaldehyde and C3H4O2
which readily loses CO to form acetaldehyde. Identify compound (A).
Chemistry : Aldehydes and Ketones

SECTION - II
SINGLE CHOICE QUESTIONS
1. Cyclohexanone on reaction with Na2CO3 solution forms

O O
OH
(a) (b)

HO
O O
OH

(c) (d)

2. is the final obtained when one of the following is reacted with base ?
CH3

O O O O

(a) H3 C CH3 (b) H3C CH3

O O O

(c) H3C CH3 (d) H3C CH3

O

3. The correct order of increasing C – O bond length of CO, CO32  and CO2 is

(a) CO2  CO32   CO (b) CO32   CO2  CO

(c) CO  CO2  CO32  (d) CO23   CO  CO 2

4. Which of the following has the most acidic hydrogen ?
(a) 3–hexanone (b) 2, 4–hexane dione
(c) 2, 5–hexanedione (d) 2, 3–hexanedione
5. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(a) MeCOCl (b) MeCHO
(c) MeCOOMe (d) MeCOOCOMe
 Chemistry : Aldehydes and Ketones

6. In the transformation
O

CH3 CH3

HO HO
The reagent is
(a) Zn/Hg conc. HCl (b) NH2NH2, OH–
(c) H2/Ni (d) NaBH4

OH
7. In Cannizzaro reaction given below : 2Ph — CHO   PhCH 2 OH  PhCO 2 the slowest step is
(a) Attack of OH– at the carbonyl group (b) Transfer of hydride to carbonyl group
(c) Abstraction of proton from carboxylic acid (d) Deportonation of Ph – CH2OH
8. Most acidic H-atom(s) that can be abstracted easily by base is present in
O O
|| ||
(a) Me  C H (b) Me  C Me
O O
|| ||
(c) Me  C CH2  C Me (d) None of these
9. Benzaldehyde undergoes condensation with another aldehyde to give cinnamaldehyde. The aldehyde is
(a) Formaldehyde (b) Propanaldehyde
(c) Acetaldehyde (d) Crotonaldehyde
10. Which of the following compounds on treatment with LiAlH4 will give a product that will give a positive
iodoform test?
(a) CH3 .CH2 CHO (b) CH3.CH2 .COOCH3
(c) CH3.CH2.OCH 2.CH3 (d) CH3COCH 3
11. Which of the following reacts with water to form very stable product?
(a) CH3Cl (b) CCl4
(c) CCl3CHO (d) CH2ClCH2Cl
O
i) NaOI, 
12. End products of the following sequence of reaction is 
ii) H + , 
 A+B
CH3

O
A & B are
I CO2H I O
(a) I and (b) I and
CH3
I I CO2H
O
I I O
O
(c) I and (d) I and

I CO2H I
Chemistry : Aldehydes and Ketones

O
Ph
13. 
OH
Ph   A. A is

O
OH
OH
Ph Ph
(a) O (b)
CO2
Ph
Ph
Ph

(c) Ph (d) None

O OH
1. OH
14. CH3CH = CH – CHO 
2. 
 A. A is

(a) CH3CH2CH2(CH = CH)2CHO (b) CH3(CH2CH2)2CH = CH – CHO

(c) CH3(CH = CH)3CHO (d) None is correct
15. Which of the following compound on treatment with LiAlH4 will give a product that will give positive
iodoform test?
(a) CH3 CH 2 CHO (b) CH3 CH 2CO 2 CH 3
(c) CH3 CH2 OCH2 CH 3 (d) CH3COCH 3
16. The product obtained by condensation of PhCHO & MeCHO are

OH OH

Ph O and Me O
(a)
CH3

OH OH

(b) Ph O and Ph O

Ph

OH OH

(c)
Ph OH and Me O

(d) None of these

 Chemistry : Aldehydes and Ketones

17. Cannizzaro reaction is not given by

(a) Trimethylacetaldehyde (b) Acetaldehyde
(c) Benzaldehyde (d) Formaldehyde
18. The compound that will not give iodoform on treatment with alkali and iodine is
(a) acetone (b) ethanol
(c) diethyl ketone (d) isopropyl alcohol
19. Which of the following compounds will react with ethanolic KCN?
(a) Ethane (b) Acetyl chloride
(c) Chlorobenzene (d) Benzaldehyde
20. Which is mixed ketone?
(a) Pentanone (b) Benzophenone
(c) Acetophenone (d) All of these
Chemistry : Aldehydes and Ketones

SECTION - III
MULTIPLE CHOICE QUESTIONS

1. OH
CH3 — CHO  CH3CH(OH)CH 2CHO
In the aldol condensation of acetaldehyde represented above, which of the following intermediate species
are obtained?

O O

(a) CH2 C H (b) :CH2 C H

OH O OH

(c) CH3 C CH2 CH (d) CH3 C O CH2 CH3

H H

2. The intermediate stages in the conversion

dil. H2SO4
(CH 3 ) 2 —C —C— (CH3 ) 2  
 CH3COC(CH3 )3 are
| |
OH OH


(a) (CH3 ) 2 —C —C(CH 3 ) 2 (b) (CH3 ) 2 —C— C(CH 3 ) 2
| | |
OH OH2 OH



(c) (CH3 ) 2 — C— C(CH3 )3 (d) CH3 —C— C(CH 3 )3
| ||
OH OH


3. Which of the following compounds will give a red precipitate on being heated with Fehling’s solution?
(a) C6 H 5CHO (b) CH3 CHO
(c) CH3 COCH3 (d) C6 H5 CH 2 CHO
4. Methylethyl ketone can be reduced to n-butane by
(a) the Meerwein-Ponndorf reduction (b) the Wolff-Kishner reduction
(c) Mg-Hg, H2O (d) HI/red phosphorus at 423 K
5. On being treated with HCl, acetone gives
(a) mesityl oxide (b) phorone
(c) mesitylene (d) aldol
 Chemistry : Aldehydes and Ketones

6. Base catalysed aldol condensation occurs with

(a) propionaldehyde (b) benzaldehyde
(c) 2-methyl propionaldehyde (d) 2, 2-dimethylpropionaldehyde
NaOH
7. 3HCHO  CH 3CHO  A
A formed can
(a) reduce Tollen’s reagent (b) give cannizzaro reaction

(c) react with Na (d) give green colour with Cr2 O72 / H 

8. Keto-enol tautomerism is observed in

O O
|| ||
(a) H5C6 — C— H (b) H5C6 — C— CH 3

O O
|| ||
(c) H5C6 — C— C6 H 5 (d) H5 C6 — C— CH 2 CH 2CH3
9. Which of the following compounds will give haloform test –
O
||
(a) CH3  CH  Br  CH 3 (b) CH3  C  CH 2 I

O
(c) C CH3 (d) None

O CH3

CF3COOH
10.   A is

O
(a) (b)
OH
O CH3
O

O O
O
(c) H3C (d) H CH3
OH
CH3
CH3
Chemistry : Aldehydes and Ketones

MISCELLANEOUS QUESTIONS
SECTION - IV
COMPREHENSION TYPE QUESTIONS
Write up - I
Carboxyl compounds containing -hydrogen atoms undergo condensation reactions involving carbanion
formation in the presence of base. Aldol, Perkin, Claisen, Dieckmann condensations are the examples
of such reactions. Let us consider aldol condensation of acetaldehyde. The product, aldol, when
heated eliminates H2O to give crotonaldehyde.

dilute 
2CH 3CHO 
OH -
 CH 3CH(OH)CH 2CHO   CH 3CH  CH  CHO

when two different carbonyl compounds undergo aldol condensation, it is known as crossed aldol
condensation. Aldol condensation can be catalysed by base as well as acid. Given below is the base
catalysed mechanism.

-
(i) HO + H CH2 CH O CH2 CH O CH2 CH O

-
O O

(ii) H3C C + CH2 CHO CH3 HC CH2CHO

-
O OH

(iii) CH3 CH CH2CHO + H2O CH3 HC CH2CHO + OH-

Step (1) is the rate -determining step at low hydroxide concentration whereas step (ii) is the rate -
determining step at normal hydroxide concentration
Open chain esters do not undergo aldol condensation but cyclic esters or lactones do. Tendency of
carbonyl compounds containing a-H to form enolate ion also facilitates halogenation at - C.
 Chemistry : Aldehydes and Ketones

1. O dilute
?
OH-
The product formed is
O O

(a) O O OH (b) O OH OH

O O

(c) (d) O O
HO OH
O
2. KOH
?
CH3
O
The major product would be
H3C OH O
O CH3
(a) (b)

O CH3
O
(c) (d)

O
+
3. CH3 D3O
R ?
The final product of this reaction would be
O
OD
CH3
(a) CH3 (b) R
R
D

O OD
CH3 CH3
(c) R (d) R
D D D
D D D
Chemistry : Aldehydes and Ketones

Write up - II
Aldehydes and ketones are amphoteric. Thus they can react both as acids and bases. Under acidic
conditions, the carbon of the protonated carbonyl group is much more electrophilic, reacting even
with weak nucelophile. Carbonyl compound gives nucleophilic addition reaction. In this reaction the
nucleophilic attack precedes the electrophilic attack.

4. Which one of the carbonyl compounds is most reactive towards NaCN/H+?

O
||
(a) C6 H 5 —C — H (b) CH 3 O CHO

O O
(c) H3C C H (d) NC C H

5. Carbonyl compound gives nucleophilic addition with

(a) carbon nucelophile (b) oxygen nucelophile
(c) Nitrogen nucleophile (d) all of these
6. Reactivity of aldehyde and ketones for nucleophilic addition reactions depends on which factors?
(a) Ability of carbonyl oxygen to carry a negative charge
(b) Nature of the group attached to the carbonyl carbon
(c) Size of the substituents
(d) all of these

MULTIPLE MATCHING TYPE QUESTIONS

7. Match List I (reaction) with List II (name of the reaction) and select the correct answer.
List I (Name of Reaction) List II (Reagent)
50% NaOH
(A) 2C6 H 5CHO   1. Benzoin condensation

50% NaOH
(B) C6 H5 CHO  HCHO   2. Cannizzaro reaction

KCN / C2 H 5OH
(C) 2C6 H 5CHO   3. Cross Cannizzaro reaction

CH3COONa
(D) C6 H5CHO  (CH 3CO)2 O 
 4. Perkin reaction

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

(a) 1 3 2 4
(b) 2 3 1 4
(c) 1 3 4 2
(d) 2 3 4 1
 Chemistry : Aldehydes and Ketones

8. Match List I with List II and select the correct answer

List I (Name of Reaction) List II (Reagent)
(A) Oppenaur oxidation 1. CrO2Cl2
(B) MPV reduction 2. RCOOOH
(C) Baeyer Villiger oxidation 3. Aluminium tertiary butoxide
(D) Etard reaction 4. Aluminium isopropoxide
(A) (B) (C) (D)
(a) 3 4 2 1
(b) 4 3 2 1
(c) 4 3 1 2
(d) 3 4 1 2

ASSERTION-REASON TYPE QUESTIONS

The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
9. Assertion : Formaldehyde is more reactive than benzaldehyde for nucleophilic addition reaction.
Reason : Formaldehyde is more stable than benzaldehyde.
10. Assertion : Chloroacetaldehyde is more reactive than acetaldehyde for nucleophilic addition reaction.
Reason : –I group in carbonyl compound makes carbonyl carbon more e– deficient.
11. Assertion : Unsymmetrical ketones react with HCN to give (d, l) mixture of cyanohydrin.
Reason : Cyanide ion is ambident nucleophile.
12. Assertion : -hydrogen atoms in aldehydes and ketones are acidic.
Reason : The anion left after the removal -H is stabilised by inductive effect.
13. Assertion : R-CO+ is more stable than R-C+=O.
Reason : Resonance in carbonyl compound provides C+ and O–.
14. Assertion : Carbonyl compounds do not show intermolecular hydrogen bonding.
Reason : Boiling points of carbonyl compounds are lower than alkanes.
15. Assertion : Carbonyl compounds undergo nucleophilic addition.
Reason : Addition of KCN solution to carbonyl compounds decreases the pH of the solution..
Chemistry : Aldehydes and Ketones

SECTION - V
(PROBLEMS )

A. Only one option is correct (Objective Questions)

CH3COONa
1. MeO CHO  (X) 
H 3O 
 MeO CH CHCOOH

the compound (X) is :

(a) CH3 —COOH (b) BrCH2—COOH
(c) (CH3 CO)2 O (d) CHO—COOH
2. How will you convert butan-2-one to propanoic acid?
(a) Tollen’s reagent (b) Fehling solution
+
(c) NaOH/I2 /H (d) NaOH/NaI/H+
3. The order of reactivity of phenyl magnesium bromide with the following compounds is :

O O O

H3C CH3 H3C H Ph Ph

(I) (II) (III)

(a) (II) > (III) > (I) (b) (I) > (III) > (II)
(c) (II) > (I) > (III) (d) all react with the same rate
2 
Hg / H
4. Ph — C  CH3   A, A is :

O
Ph Ph
(a) (b) O
H3C H3C

OH
Ph Ph
(c) (d) OH
H3C H3 C
 Chemistry : Aldehydes and Ketones

CHO OHC

o
(i) NaOH /100 C
5. 
(ii) H  / H O

2

CHO OHC
Major product is :
COOH HOOC OH HOOC

(a) (b)

COOH COOH HO
HOOC

O
O CH 2 OH COOH

(c) (d)

O COOH CH2 OH
O

6. 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 and sodium acetate gives a
product C. Identify the structure of C :

(a) CH3 CH 2 CH  N  NHCONH 2 (b) CH3 —C  N  NHCONH 2

|
CH3

(c) CH3 —C  N  CONHNH 2 (d) CH3 CH 2 CH  N  CONHNH 2

|
CH3

7. 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
8. Which one of the following will most readily be dehydrated in acidic condition :
O OH OH
(a) (b)

O O

(c) (d)
OH OH
Chemistry : Aldehydes and Ketones

9. The appropriate reagent for the following transformation :

O
CH2 CH3
CH3

HO HO

(a) Zn(Hg), HCl (b) NH2NH2, OH–

(c) H2/Ni (d) NaBH 4
10. Which of the following has the most acidic hydrogen?
(a) 3-hexanone (b) 2, 4-hexanedione
(c) 2, 5-hexanedione (d) 2, 3-hexanedione
11. The enol form of acetone, after treatment with D2O, gives :

OD O
| ||
(a) CH3 —C  CH 2 (b) CD3 —C — CD3

OH OD
| |
(c) CH 2  C — CH 2 D (d) CD3 —C  CD 2

12. Which of the following will react with water?

(a) CHCl3 (b) Cl3 C·CHO
(c) CCl4 (d) ClCH2 CH2Cl
13. In the Cannizaro’s reaction given below :

OH
2Ph — CHO   Ph — CH 2 OH  PhCO 2


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
14. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives :
(a) potassium m-chlorobenzoate and m-chlorobenzyl alcohol
(b) m-hydroxy benzaldehyde and m-chlorobenzyl alcohol
(c) m-chlorobenzyl alcohol and m-hydroxy benzyl alcohol
(d) potassium m-chlorobenzoate and m-hydroxy benzaldehyde
15. Which of the following compounds is oxidised to prepare methyl-ethyl ketone?
(a) 2-propanol (b) 1-butanol
(c) 2-butanol (d) t-butyl alcohol
 Chemistry : Aldehydes and Ketones

16. The compound that will not give iodoform on treatment with alkali and iodine is :
(a) acetone (b) ethanol
(c) diethyl ketone (d) isopropyl alcohol
17. The Cannizaro’s reaction is not given by :
(a) trimethyl acetaldehyde (b) acetaldehyde
(c) benzaldehyde (d) formaldehyde
18. When acetaldehyde is heated with Fehling’s solution, it gives a precipitate of :
(a) Cu (b) CuO
(c) Cu2 O (d) Cu + Cu2O + CuO

B. More than one options are correct (Objective Questions)

1. Base catalysed aldol condensation occurs with :
(a) propionaldehyde (b) benzaldehyde
(c) 2-methyl propionaldehyde (d) 2, 2-dimethyl propionaldehyde
2. Which of the following compounds will give a yellow precipitate with iodine and alkali?
(a) 2-hydroxy propane (b) Acetophenone
(c) Methyl acetate (d) Acetamide
3. Which of the following compounds will react with ethanolic KCN?
(a) Ethyl chloride (b) Acetyl chloride
(c) Chlorobenzene (d) Benzaldehyde
4. Which of the following are the examples of aldol condensation?
dil. NaOH
(a) 2CH 3CHO   CH 3CHOHCH 2 CHO
dil. NaOH
(b) 2CH 3COCH 3   CH3CHOHCH 2CH 2 COCH 3
dil. NaOH
(c) 2HCHO   CH3OH
dil. NaOH
(d) C6 H5 CHO  HCHO   C6 H 5CH 2OH
5. A new carbon-carbon bond formation is possible in :
(a) Cannizaro’s reaction (b) Friedal Crafts’s reaction
(c) Clemmensen reduction (d) Reimer-Tiemann reaction
6. Among the following compounds, which will react with acetone to give a product containing
>C=N—?
(a) C6 H 5 NH 2 (b) (CH3 ) 3 N
(c) C6 H 5 NHC 6 H 4 (d) C6 H 5 NHNH 2
7. Which of the following will undergo aldol condensation?
(a) Acetaldehyde (b) Propanaldehyde
(c) Benzaldehyde (d) Trideutereo acetaldehyde
Chemistry : Aldehydes and Ketones

8. Which of the following reactants on reaction with conc. NaOH followed by acidification gives following
lactone as the :
O
C
O
CH2

COOCH3 COOH
(a) (b)
COOH CHO

CHO COOH
(c) (d)

CHO COOH
9. The smallest ketone and its next homologue are reacted with NH2OH to form oxime :
(a) two different oximes are formed (b) three different oximes are formed
(c) two oximes are optically active (d) all oximes are optically active

SUBJECTIVE QUESTIONS
1. Write the structure of the major organic product expected from the following reaction.

KOH
H3 CO CHO  HCHO  

2. How will you bring about the following conversions? “4-nitrobenzaldehyde from benzene.”

3. Complete the following reaction with appropriate structure :

NaOC 2 H 5 in absolute
C6 H 5 — CHO  CH 3 — COOC 2 H 5 
C H OH and heat
A
2 5

4. Complete the following reaction with appropriate structure :

CH3 CH2
(i) KCN / H 2SO 4
C O 
(ii) LiAlH4
A
H
5. Suggest appropriate structures for the missing compounds.
(The number of carbon atoms remains the same throughout the reaction)
CH3


Dil. KMnO 4 HIO 4 OH
  A   B  C

CH3
 Chemistry : Aldehydes and Ketones

6. Complete the following, giving the structures of the principal organic products :

(i)  Ph 3 P  CH 2 
A

R C C R  HClO 4 
B
(R  n  Pr)
C
O
(ii) ClCH2CH2CH2COPh + KOH + MeOH  C
7. Acetophenone on reaction with hydroxyl amine hydrochloride can produce two isomeric oximes. Write
structures of the oxime.
8. An aldehyde A (C11H8O), which does not undergo self aldol condensation, gives benzaldehyde and two
moles of B on ozonolysis. Compound B, on oxidation with silver ion gives oxalic acid. Identify the
compounds A and B.
9. Write the intermediate steps for each of the following reactions :

H3O
(i) C6 H 5CH(OH)C  CH   C6 H 5CH  CHCHO


H
(ii) 
CH3 O CH3

10. Explain why o-hydroxy benzaldehyde is a liquid at room temperature while p-hydroxy benzaldehyde is
a high melting solid :
11. Carry out the following transformation is not more than three steps :
O
||
CH3 — CH 2 — C  C — H 
 CH3 — CH 2 — CH 2 —C — CH 3
12. What would be the major product in the following reaction :

Ph
Base
 
O
Br
13. An organic compound A C6H10O, on reaction with CH3MgBr followed by acid treatment gives compound
B. The compound B on ozonolysis gives compound C, which in presence of a base gives 1-acetyl
cyclopentane D. The compound B on reaction with HBr gives compound E. Write the structures of A,
B, C, D and E. Show how D is formed from C.
Chemistry : Aldehydes and Ketones

14. An alkene (A) C16H16 on ozonolysis gives only one product (B) C8H8O. Compound (B) on reaction
with NaOH/I2 yields sodium benzoate. Compound (B) reacts with KOH/NH2NH2 yielding a hydrocarbon
(C) C8H10. Write the structures of compounds (B) and (C). Based on this information two isomeric
structures can be proposed for alkene (A). Write their structures and identify the isomer which on
catalytic hydrogenation (H2/Pd—C) gives a racemic mixture.
15. Write structures of the products A, B, C, D and E in the following scheme :


CH 2 CH 2 CH 3 
Cl2 / FeCl3 Na  Hg / HCl
 A  HNO3 / H 2SO 4
 B  CH 2 CHCH 2ONa
 C  H 2 / Pd / C
 D  E

Cl
 Chemistry : Aldehydes and Ketones

ANSWERS

EXERCISE - 1
O
(a) A 
 H2 C CH2 C CH3 (b) B 
 No reaction
O
||
C— CH 2 — CH 3
(c)

CH3 CH3

(d) A 
 OH ; B 
 OH
OH O

EXERCISE - 2
O
O
A 
 C CH3 B 
 CH2 C H

CF 3
O
C 


OMe

EXERCISE - 3
NaHSO3 is used to separate this, it forms white crystalline solids of bisulfite compounds with carbonyls
OH
C = O + NaHSO3  C
SO3Na
[bisulfite compound]

Also bisulfite compounds can regenerate carbonyl compound when heated with dilute acid.
Chemistry : Aldehydes and Ketones

EXERCISE - 4
For nucelophilic addition - elimination, there must be free lone pair of electrons on N-atom. But
here, the lone pair of N-atom being in conjugation taks part in resonance, thereby the lone pair of
electron on N-atom is not available. Hence this compound cannot undergo nucleophilic addition -
elimination

EXERCISE - 5
1 2 3
In Semicarbazide NH2  NH  C  NH2 which nitrogen will undergo nucleophilic addition -
||
O
elimination reaction N(1) will undergo nucleophilic addition - elimination reaction, because it will
have lone pair of electron which is essential condition for aforesaid reaction, but N(2) and N(3) will
not have free lone pair of electron due to resonance.

EXERCISE - 6
O O
|| ||
P 
 CH3 — C— C— CH3

EXERCISE - 7

(A) —CH  CH — CH 2 — CH 2OH

(B) —CH 2 — CH 2 — CH 2 — CH 2 OH

(C) —CH 2 — CH 2 — CH 2 — CH 2 OH

(D) —CH 2 — CH 2 — CH 2 — CH 2 OH

EXERCISE – 8
CH 3 — CH  CH — CHO

HO
H+
HO

O
CH3 CH CH CH
O
Ni./ H 2

O
CH3 CH2 CH2 CH
O

N2O / H

CH 3 — CH 2 — CH 2 — CHO
 Chemistry : Aldehydes and Ketones

EXERCISE – 9
The dianion shown by structure (II) will show faster cannizaro’s reaction than that of the monoanion
shown by structure because dianion will give more resonance stabilized carboxylate ion.

EXERCISE – 10

O OH OH O
|| | | ||
P  D — C— O or D — C — H Q  D — C — H, D — C— O
| |
H H

SECTION - I
(Subjective Questions)

Answers are given in the separate booklet (Level – I to Level – III)

SECTION - II
(Single Choice Questions)
1. (a) 2. (a)
3. (c) 4. (b)
5. (a) 6. (b)
7. (b) 8. (c)
9. (c) 10. (d)
11. (c) 12. (b)
13. (b) 14. (c)
15. (d) 16. (a)
17. (b) 18. (c)
19. (d) 20. (c)

SECTION - III
(Multiple Choice Questions)
1. (a, b, c) 2. (a, b, c, d)
3. (b, d) 4. (b, d)
5. (a, b) 6. (a, c)
7. (a, b, c) 8. (b, d)
9. (a, b, c) 10. (a)
Chemistry : Aldehydes and Ketones

SECTION - IV
(Comprehension Type Questions)
1. (d) 2. (a)
3. (c) 4. (d)
5. (d) 6. (d)

(Multiple Matching Type Questions)

7. (b) 8. (a)

(Assertion Reason Type Questions)

9. (c) 10. (a)
11. (b) 12. (c)
13. (b) 14. (c)
15. (c)

SECTION - V

A. Only one option is correct (Objective Questions)

1. (c) 2. (c)
3. (c) 4. (a)
5. (d) 6. (a)
7. (a) 8. (a)
9. (b) 10. (b)
11. (b) 12. (b)
13. (b) 14. (d)
15. (c) 16. (c)
17. (b) 18. (c)
 Chemistry : Aldehydes and Ketones

B. More than one options are correct (Objective Questions)

1. (a, c) 2. (a, b)
3. (a, b, d) 4. (a, b)
5. (b, d) 6. (a, d)
7. (a, b, d) 8. (c)
9. (b)

SUBJECTIVE
Answers are given in the separate booklet.