Aldehydes and Ketones Homework

Solutions to HWS-2
Home Worksheet-3
 Class-2-OCOC-II

Reactions of Aldehydes & Ketones

I. Typical (Direct) Nucleophilic Addition :

1. Of Hydride ion (H ) : LiAlH4 /ether or NaBH4 /H 2O
2. Of Alkynide ion (R-C C-Na)
+
3. Of H 2 O/H (Hydration)
4. (a) Of ROH/H (b) Of Glycols (c) Of 1,3 Diols
+

5. Of HCN/KOH
6. Of NaHSO3 (Bisulphate addition)
7. Of Grignard Reagent
8. Of Ylides (Wittig Reaction)
9. Of Ammonia & it’s derivatives
(a) of ammonia (b) of Amines (RNH2 & RNHR)
(c) of special derivatives (NH Y)
2 (d) Reductive amination
Chemistry Aldehydes & Ketones Home Work Sheet-2 Solutions

1 Phenolic
1- Cztlscoc / Et
O
q
' -
-

ester
O

A' ☐ 3
't Et PET pH
f
HO -

60°C Fries
-

1. Naps ,+¢ 2h
dust
do Et
rearrangement
#
:

HYO fit CHCH }

41+0
03
CHZCHO 1-

2h

14
1 -

CHzCH=CHz 1-1 14
2-
BY KOH
=

200°C ,CHzCH=CHz
+
14

Claisen rearrangement
03
14
14 - ^
_ CHZCHO
It
-4=0 +
H
 8-1 8-
3. CH3C=_ CH +
MeMgBr Melt +
CHzC-=É-ÑgBr
PH NaBHq
ph-coclph-CH-C-IC-c.it
Ph
}
-
C -
CIC -
CH
}

◦ o_0 o_0 o
(CHZOH)z I LiAlH4
4.
→
#
I Hzot
At 11-20
→

\C00Me \cooMe
lemon \CHs0H
protecting 7=0 group
0
11-1-10
0 °

11 11 (-11-20)
4
z z
4
3 2 43 z
◦
ʰ
-1+5
&±
ʰ 4
5 / - +
5 s
,
•

11°
g
0 7
2

5
11 5 4 3
• '
-
_

t.cl#z
14
3

+
G 2
6 2
-

Ht

( major)
 5. Photo
HCN

KOH
Ph -
É
GH
-
an + Ph -

CH
GH
-
COOH

(A)
tiAlH4 Ph
PCC
Ph C cook
(C)
-
-

-
CH -

CH ,
61-1 bit 1+20

Ph -
É -
an
R2 Rz
Ph
#
(A)
bit
JIBAL It -

"
" -8¥ ,
(C)

6. Br + PhzÉ →
F- Phz É P -

Phz
\Br -

HBR (A)

( O)
P Phz i. CHZ +
0=01-2
Coco
- +

(A) ( ACHO )

H HCN

KOH
CN
 OH
OH /
OH /
/
alk
H

1H
.

7- H H
,
-

Kmn 04
O
^ 0
(O )
( syn )
H
\,
Met -
Me
⇐ "3) zco
(acetal formation)
H+
4° 1+30-1 ↑
"

1
#
It H O O

I I \/

HO OH
Met -
Me

8 R'
.

CHS OET R2 R3 C -CH=CHz

CHZ
§ § City
-
- - -
-

⇐ 1-1201-1)z/ Ht hitting 11-30-40 8

• Protect carbonyl group with @ 11-201+12/ Ht

; Use
Li At Hq to

reduce ester to alcohol

dehydrate; using alcohol

H% & then hydrolyse acetal to get final product .

9 . H+

HIGH
' '

OH OH
-

HO HO
-1 0 y

H+
1

'

110

SNY diols forms cyclic ethers

10 .

HAN H Na H

OH CN ETOH CHZNHZ
redn .
of
cyanide
5
H 4 H HNOZ
LH
5 6

CHzÑz
+
'
N2
4-1-12
-

4 3 -
-

✓
-
-
-

2
3 z

° Me
+ CHZ
"
1. MeMgBr -

n -1
z.Hzo
-

(major) ( Minor)
 Chemistry Aldehydes & Ketones Home Work Sheet-3
<

1. + Nitz -1¥ N will discuss in class .

(-1-120)

2 It
-1¥
.
N -

NH
}
(-1-120)

#
+ H CONH Ph
3h CONHZ
-

3. Photo NHZOH HZSOT

→
HCl ( Benzamide) ( N Phenyl
-

formamide )
PHCONH Me 1- Meco NHPH (N Phenyl ethanamide)
Ph\c=O
-

NHZOH 42504
benzamide
→ N
Methyl
-

/
Me

42504 will discuss in class

5.
4204
µ (Ring expansion occurs
) .

HCl

6 . Give the products .

( Cannizzaro Reaction)
7.

8 .

9. 2 H -
É -

☐
°#
(A- 1- B)
It -1
C
4oz

8D It -1
10 . 2 HCHO (A- 1- B) C
☐ 20 400C

11 .
D- § -

☐
OH
_

(A- + B)
1- iAlH4
Products
Ether

Ht
C
40°C
 Vidyamandir Classes

45 -50min

Organic Chemistry Aldehydes & Ketones Class Test-2

For each question choose the correct alternative Only One choice is correct. However, questions marked
with '*' may have More than One correct option :

1. Which of the following compounds does not react with sodium bisulphate ?
(A) Benzaldehyde (B) Acetone (C) Butanone (D) Acetaldehyde

2. A mixture of Benzaldehyde and Formaldehyde on heating with aq NaOH solution gives :

(A) sodium benzoate and methyl alcohol (B) sodium benzoate and ethyl alcohol
(C) benzyl alcohol and methyl alcohol (D) benzyl alcohol and sodium formate

3. Acetaldehyde forms a white crystalline compound on mixing with a….. solution of…. :
(A) Acidic Zn, Hg (B) Alcoholic Na 2SO3
(C) Saturated, aqueous NaHSO3 (D) Aqueous NaCl

4. CH 3CHO  NH 2OH  Y. The number of  bonds,  -bonds and lone pairs of electrons in the compound
‘Y’ are respectively :
(A) 9, 1, 4 (B) 11, 1, 5 (C) 9, 2, 2 (D) 8, 1, 3

*5. A carbonyl compound reacts with hydrogen cyanide to form cyanohydrin which on hydrolysis forms a
racemic mixture of  -hydroxy acid. The carbonyl compound is :
(A) formaldehyde (B) acetaldehyde (C) acetone (D) benzaldehyde

*6. Which of the following undergoes cannizaro reaction ?

(A) HCHO (B) C6 H5CHO (C) Cl3C  CHO (D)  CH3 3 C  CHO

7. A new C  C bond formation is possible in :

(A) Cannizaro reaction (B) Rosenmund’s reduction
(C) Acetal formation (D) Wittig reaction

(1) CrO Cl / CS OH 
8. C6 H5 CH3 
2 2

2
 (A) 
 (B)
H3O

The conversion of A to B is called as :

(A) Cannizaro reaction (B) Aldol Condenation
(C) Clemmenson reduction (D) Etard reaction

9. A substance C4 H10 O on oxidation yields compound C4 H8O. Which gives an oxime and a positive
iodoform test. The original substance on treatment with conc. H 2SO 4 gives C4 H8 . The compound is :
(A) CH 3CH 2CH 2 CH 2OH (B) CH 3CHOHCH 2 CH3
(C)  CH3 3 COH (D) CH 3CH 2  O  CH 2CH3

VMC | Organic Chemistry 1 Class Test-2 | Aldehydes & Ketones

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10. What is the product of Cannizzaro reaction of glyoxal ?

(A) COOH (B) C HO (C) C OO  (D) C HO
| | | |
COOH COOH CH 2 OH CH 2 OH

 PhCH 2OH  PhCO 2 . The slowest step is :
OH
11. In the cannizaro reaction given : 2PhCHO 
(A) The attack of OH  at the carbonyl group
(B) The transfer of hydride to the carbonyl group
(C) The abstraction of proton form the carboxylic group
(D) Deprotonation of phCH 2 OH

NaNH 2 Ph  CHO MnO 2

12. Et  C  CH   
H O
   X:
2

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

13. The major product obtained in the reaction: is :

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

O
3 2 2(CH OH)
14. C2 H 4  A 

 B . The product B is :
Zn H

(A) H 2C  CH(OCH3 )2 (B)

(C) (D) HCHO

15.  CH3 2 C  CHCOCH3 can be oxidised to  CH3 2 C  CHCOOH by :

1. NaOH / I
(A) chromic acid (B) 

2
 (C) Cu at 300°C (D) KMnO 4
2. H

16. The smallest ketone and its next homologue are reacted with NH 2 OH to form oxime :
(A) two different oximes are formed (B) three different oximes are formed
(C) two oximes are optically formed (D) all oximes are optically active

17. If 3-hexanone is reacted with NaBH 4 followed by hydrolysis with D 2O, the product will be :
(A) CH 3CH 2 CH  OH  CH 2 CH 2 CH3 (B) CH3 CH 2 CD  OH  CH 2 CH 2 CH 3
(C) CH 3CH 2 CH  OD  CH 2 CH 2 CH 3 (D) CH 3CH 2 CD  OD  CH 2 CH 2 CH 3

18. What will be the final product when cyclohex-2-enone is selectively reduced in MPV reaction ?
(A) Cyclohexanol (B) Cyclohex-2-en-1-ol
(C) Cyclohexanone (D) Cyclohex-3-en-1-ol

VMC | Organic Chemistry 2 Class Test-2 | Aldehydes & Ketones

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19. What is the product obtained in the reaction of Acetaldehyde with semicarbazide ?
O
||
(A) H3 C  CH  N  NH  C  NH 2 (B) H3C  CH  N  NH 2
O
||
(C) H3C  CH  N  OH (D) H3 C  C  N  NH  C  NH 2
|
CH3
20. What are the products A, B, C in the following reactions ?
I.  CH3CO2 2 Ca 
 A II. CH 3CO2 H 
HI
Red P
B
4 10 P O
III. 2 CH3CO 2H 

C
A B C
(A) C2 H 6 CH 3COCH3  CH3CO 2 O
(B)  CH3CO 2 O C2 H 6 CH 3COCH3
(C) CH3COCH 3 C2 H 6  CH3CO 2 O
(D) CH3COCH 3 C2 H 6 CH3COOH

NaNH H
21. 2PhCHO  HC  CH 
2
 
 Product formed is :
(A) PhCH(OH)  C  C  H (B) PhCH(OH)  C  C  CH(OH)Ph
(C) PhCH  CH  C  CH (D) PhCH( C  CH)2

22. Iodoform can be prepared from all except :

(A) Ethyl methyl ketone (B) Isopropyl alcohol
(C) 3-Methyl-2-butanone (D) Isobutyl alcohol

23. Which of the following give most stable hydrate with H2O/H+ ?
(A) CH 3CHO (B) HCHO (C) CCl3CHO (D) PhCHO


24.  CH3  2 CO 
NaCN
 HCl 
H3 O
A  B. In the given sequence of reactions A and B are :

(A)  CH3  2 C  OH  CN,  CH3 2 C  OH  COOH

(B)  CH3 2 C  OH  CN,  CH 3  2 C  OH 2 
(C)  CH3 2 C  OH  CN,  CH3 2 CHCOOH
(D)  CH3  2 C  OH  CN,  CH3 2 C  O
25. The most reactive compound towards formation of cyanohydrin on treatment with KCN followed by
acidification is :
(A) benzaldehyde (B) p-nitrobenzaldehyde
(C) p-chlorobenzaldehyde (D) p-hydroxybenzaldehyde

26. Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a
compound if water during the reaction is continuously removed. The compound formed is generally known
as :
(A) A Schiff’s base (B) An enamine (C) An imine (D) An amine

VMC | Organic Chemistry 3 Class Test-2 | Aldehydes & Ketones

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27. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives :

(A) potassium m-chlorobenzaldehyde and m-hydroxy benzaldehyde
(B) m-hydroxy benzaldehyde and m-chlorobenzaldehyde
(C) m-chlorobenzyl alcohol and m-hydroxy benzyl alcohol
(D) potassium m-chlorobenzoate and m-chloro benzyl alcohol

28. CH 3CHO  NH 2OH  CH3CH  N  OH. The above reaction is carried out at :
(A) pH  1 (B) pH  4.5 (C) pH  12 (D) pH  14

*29. Which of the following statements regarding aldehydes is(are) correct ?

(A) The carbonyl functional group is planar
(B) The boiling points of aldehydes is greater than those of alkanes of comparable molar masses
(C) The boiling points of aldehydes is greater than those of alcohols of comparable molar masses
(D) Formaldehyde is gas at room temperature

30. Identify the product (B) :

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

VMC | Organic Chemistry 4 Class Test-2 | Aldehydes & Ketones

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ANSWER KEY FOR PART TEST-2/Aldehydes & Ketones (Properties)

1 2 3 4 5 6 7 8 9 10

C •oo
B C D BD ABD D A B C

11 12 13 14 15 16 17 18 19 20

B D C B B B C B A C

21 22 23 24 25 26 27 28 29 30

B D C A B B D B ABD B

VMC | Organic Chemistry 5 Class Test-2 | Aldehydes & Ketones