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Chapter 15: Q47P (page 724)

How could you synthesize the following compounds starting with a carboxylic acid?

Short Answer

Expert verified

The reaction followed as:

b.

Step by step solution

01

Formation of ether from carboxylic acid

Carboxylic acid directly does not lead to ether formation of carboxylic acid derivate is formed that is acyl chloride on the reaction of a carboxylic acid with the thionyl chloride or phosphorous trichloride after abstraction of proton of carboxylic acid they attached to it and make a good leave group and form acyl chloride which on reaction with alcohol from the ether.

02

Mechanism

Mechanism followed as:

  1. Reaction of a carboxylic acid with thionyl chloride

  2. Formation of acyl chloride occur

  3. Reaction of an acyl chloride with alcohol

  4. Removal of HCl occur

  5. Formation of ether occurred

03

Formation of amide from carboxylic acid

Similarly, a carboxylic acid forms its derivative acyl chloride on reaction with thionyl chloride, and the reaction followed by reacting with two equivalent amines and amide formation occurs followed by removal of HCl as followed:

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Most popular questions from this chapter

Problem:D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C-O bond, rather than the alkyl C-O bond, by studying the hydrolysis

of the following ester under basic conditions:

a. What products contained the label?

b. What product would have contained the label if the alkyl C-O bond had broken?

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

  1. Pentylamine

  2. Iso hexyl amine

  3. Benzylamine

  4. Cyclohexylamine

a. Which compound has the stretching vibration for its carbonyl group at the highest frequency: acetyl chloride, methyl acetate, or acetamide?

b. Which one has the stretching vibration for its carbonyl group at the lowest frequency?

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.

Rank the following compounds in order of decreasing frequency of the carbon-oxygen double bond stretch
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