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Question:

Predict the main product of the following reactions?

Solution:

(i) 3-oxocyclohexane-1-carbaldehyde reacts with Tollen's reagent ([Ag(NH3)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.
CH2−CO||−CH2−CO||−OCH3 (methyl acetoacetate) →(ii)H+(i)NaBH4 CH2−CHOH|−CH2−CO||−OCH3 (methyl-3-hydroxybutanoate)
(iii) It is a cross aldol condensation reaction and the product formed is cinnemaldehyde.
C6H5−CHO + CH3−CHO → dil. NaOH C6H5−CH=CH−CH3 (Cinnemaldehyde)