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Chapter 18: PROBLEM 18.34 (page 958)

Question: Predict the major products of the following reactions.

a.

b.

c.

d.,

Short Answer

Expert verified

Answer

a.

b.

c,

d.

Step by step solution

01

Organic reactions of aldehyde

Aldehydes can be easily oxidized to carboxylic acid by treating with common oxidants. The example of oxidants are potassium permanganate, chromic acid, sodium hypochlorite, silver oxide and peroxy acids etc.

02

Major product of the reaction

a. Aldehyde part can be oxidized to its corresponding carboxylic acid in the presence of a mild oxidizing agent like silver oxide (Ag2O) .

Formation of major product

b. Potassium dichromate (K2Cr2O7) solution acidified with sulfuric acid (H2SO4) oxidizes aldehyde part to its corresponding carboxylic acid and secondary alcohol is also oxidised to ketone group.

Formation of major product

c. Tollens reagent, Ag(NH3)2OH has no effect on simple hydrocarbons, ethers, ketones and alcohols also. In this reaction, tollens reagent oxidizes aldehyde part to its corresponding carboxylic acid and the ketone part remains unreactive.

Formation of major product

d. Potassium permanganate (KMnO4) under cold and dilute conditions, oxidizes aldehyde part to its corresponding carboxylic acid while the alkene part of the compound gets converted to diols.

Formation of major product

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Most popular questions from this chapter


Propose mechanisms for the following reactions.

Show how you would accomplish the following synthesis.

(a) Acetphenone→ acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol →2-hydroxyheptanoic acid

Predict the products of the following reactions.

(a) CH3CH2CH2C≡N+CH3CH2MgBr,thenH3O+

(b) CH3CH2CH2C≡N+DIBAL-H,thenH3O+

(c) Benzylchloride+potassiumcyanide

(d) Productofc+cyclopentylmagnesiumchloride,thenacidichydrolysis

(e) Productofc+DIBAL-H,thenhydrolysis

Depending on the reaction conditions, two different imines of formula C8H9N might be formed by the reaction of benzaldehyde with methylamine. Explain, and give the structures of two imines.

Question. One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts and show why this mechanism does not work for the other one.
See all solutions

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