Carbonyl Compounds: SEM-3, CC-7 Problems: Assignment 1

CARBONYL COMPOUNDS
SEM-3, CC-7
Problems: Assignment 1
Dr. Kalyan Kumar Mandal

Associate Professor
St. Paul’s C. M. College
Kolkata
Multiple Choice Questions
1. The major product of the following reaction is:
a) CH3CH(OH)CH2CHO
b) CH3CO2CH2CH3
c) CH3CH2CO2CH3
d) CH3CH2CH(OH)CHO
2. Which of the following statements regarding acetal/hemiacetal is wrong?

a) Acetals are stable in acids.
b) Acetals are stable in bases.
c) Hemiacetals are stable in acids.
d) hemiacetals are stable in bases.
3. Which of the following compounds do not undergo Cannizzaro reaction?

c) CH3CHO b) PhCHO c) HCHO d) (CH3)3CCHO
4. Which of the following is the optimum condition regarding the formation of semicarbazones of a ketone?
a) Neutral pH
b) Weakly acidic pH (≈ 5.0)
c) Alkaline pH
d) Strongly acidic pH ( < 1)
5. The most suitable base in the following reaction is
a) NaOH b) NaOEt c) NaOMe d) NaNH2
6) A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
a) benzyl alcohol + sodium formate
b) sodium benzoate + methanol
c) benzyl alcohol + methanol
d) sodium benzoate + sodium formate
7. Under Wolff-Kishner reduction conditions, the conversion which may be brought about is:
a) cyclohexanone into cyclohexane b) benzaldehyde into benzyl alcohol
b) cyclohexanone into cyclohexanol d) benzophenone into benzhydryl alcohol
8. Why is sodium borohydride an important reagent in reducing a ketone?

a) It is good for hydrolysis type reactions b) It is a good source of the hydride ion (H-)
b) It can act as a base d) It can act as a free radical initiator.
9. Compound 'A' undergoes formation of cyanohydrins which on hydrolysis gives lactic acid
[CH3CH(OH)COOH]. Therefore, compound 'A' is:
a) Formaldehyde b) Acetaldehyde c) Benzaldehyde d) Propanaldehyde
10. Acetone is treated with excess of ethanol in the presence of hydrochloric acid. The product obtained is:
•
Answer the Questions
1) Explain why base catalysed bromination of acetone leads to the formation of a tribromo
derivative with all the bromines are introduced on the same carbon atom. What product/s
do you expect if the reaction is carried out in acidic medium and why?
2) Semicarbazide hydrochloride alone does not react with a ketone to give semicarbazone
but when mixed with sodium acetate it does-why? Which nitrogen is involved in the
reaction and why? Do you expect semicarbazone formation if the ketone is treated with
semicarbazide itself in aqueous ethanol solution?
3) In Knoevenagel reaction use of excess methylene compound is not recommended.
Explain.
4) In Cannizzaro reaction involving benzaldehyde, part of the material is reduced to the
alcohol. Write the mechanism of the reaction and establish the mechanism using D2O and
PhCDO.
5) Explain the role of Li+ ion in the reduction of carbonyl compounds with LiAlH4. Give the
mechanism of the reaction.
6) Explain the role of Na+ ion in the NaBH4 reduction of a ketone (i) in aqueous medium and
(ii) in dry THF medium.
7) p-Dimethylaminobenzaldehyde fails to undergo benzoin condensation but when treated
with benzaldehyde, the condensation does occur. Explain the observation.
8) When acetaldehyde is treated with a base, aldol is obtained in a fairly good yield but when
acetone is treated in the same way, the yield of diacetone alcohol is extremely low-explain
why? How would you improve the yield of diacetone alcohol?
9) Phenylhydrazine hydrochloride does not react with a ketone, but when mixed with sodium
acetate it does-why?
10) Acetals are stable towards alkali but susceptible to acid hydrolysis. Justify.
11) Acetone, in dilute aqueous solution is 100 per cent unhydrated. When acetone is dissolved
in water enriched with O18, recovered acetone contains O18. explain
12) Semicarbazide (1 mole) is added to a mixture of cyclohexanone (1 mole) and
benzaldehyde (1 mole). If the product is isolated immediately, it consists almost entirely
of the semicarbazone of cyclohexanone; if the product is isolated after several hours, it
consists almost entirely of the semicarbazone of benzaldehyde. How do you for these
observations.
13) Select the best way for reducing carbonyl (C=O to CH2) in each of the following reactions
with reasons: (i) BrCH2CH2CHO, (ii) (CH3)2C(OH)CH2CH2COCH3
14) What are the products obtained when a mixture of CH3CH=O and H2C=O is treated with
Al(OEt)3? Explain with mechanism.
15) Explain why an aqueous of sodium cyanide is not an effective reagent for cyanohydrin
formation.
16) Explain why p-nitrobenzaldehyde does not undergo benzoin condensation but
o-nitrobenzaldehyde does.
17) Explain why the following aldehydes with no α-hydrogen atom do not undergo the
Cannizzaro reaction. (i) p-hydroxybenzaldehyde; (ii) Cl3CCHO
18) How would you convert CH3CHO to CH3CDO? Is it a case of umpolung?
19) Acetone gives monobromoacetone when brominated in presence of glacial AcOH.
Explain the observation.
20) Convert: Propionaldehyde to butanone

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CARBONYL COMPOUNDS

Dr. Kalyan Kumar Mandal

2. Which of the following statements regarding acetal/hemiacetal is wrong?

3. Which of the following compounds do not undergo Cannizzaro reaction?

5. The most suitable base in the following reaction is

a) NaOH b) NaOEt c) NaOMe d) NaNH2

a) cyclohexanone into cyclohexane b) benzaldehyde into benzyl alcohol

b) cyclohexanone into cyclohexanol d) benzophenone into benzhydryl alcohol

8. Why is sodium borohydride an important reagent in reducing a ketone?

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