Question

27. Predict the product(s) of the following reactions and the mechanism of their formation.
OH OH
OH OH
H2SO4
(ii) CoH5-C-C-C6H5
д
(i) C6H5-C-C-Et
1 1
H Et
H3C6 CH3
OYOYT​

Answer 1

Explanation:

(i) 3-oxocyclohexane-1-carbaldehyde reacts with Tollen's reagent ([Ag(NH

3

)

2

]

+

) to give 3-oxocyclohexane-1-carboxylic acid (Image).

(ii) Sodium borohydride selectively reduces keto functional group of methyl acetocetate and forms methyl-3-hydroxybutanoate.

(methyl acetoacetate)

CH

2

−

C

∣∣

O

−CH

2

−

C

∣∣

O

−OCH

3

(i)NaBH

4

(ii)H

+

(methyl-3-hydroxybutanoate)

CH

2

−

CH

∣

OH

−CH

2

−

C

∣∣

O

−OCH

3

(iii) It is a cross aldol condensation reaction and the product formed is cinnemaldehyde.

C

6

H

5

−CHO+CH

3

−CHO

dil. NaOH

(Cinnemaldehyde)

C

6

H

5

−CH=CH−CH

3