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Chapter 20: Q18E (page 653)

would you expect the following carboxylic acid to be more acidic or less acidic than benzoic acid? Explain (Reddish brown=Br)

Short Answer

Expert verified

To check whether the carboxylic acid is more or less acidic than benzoic acid.

Step by step solution

01

Representation of model is p-bromobenzoic acid(a)

The compound model can be represented as,

The para positive which is present in p-bromobenzoic acid contains bromine is an electron withdrawing group. It will stabilize the anion of p-bromobenzoyate which produces the p-bromobenzoic acid which lose proton both by inductive and resonance effects.

Thus, p-bromobenzoic acid is more acidic compared to benzoic acid.

02

Representation of model is p-(N,N-dimethylamino) benzoic acid(b)

The compound model can be represented as,

The presence of N,N-dimethylamino group which present in the para positive in p-(N,N-dimethylamino) benzoic acid results in electron releasing group. It can de-stabilize the production of p-(N,N-dimethylamino) benzoyate anion.

Thus, It is more acidic than benzoic acid.

Thus p-bromobenzoic acid is more stable then p-( N,N diethyl amino) benzoic acid.

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Most popular questions from this chapter

Arrange the compounds in each of the following sets in order of increasing basicity:

(a) Magnesium acetate, magnesium hydroxide, methyl magnesium bromide

(b) Sodium benzoate, sodium p-nitrobenzoate, sodium acetylide

(c) Lithium hydroxide, lithium ethoxide, lithium formate

How would you prepare the following compounds from benzene? More than one step is required in each case.

  1. m-Chlorobenzoic acid
  2. p-Bromobenzoic acid
  3. Phenylacetic acid, C6H5CH2CO2H

Propose a synthesis of the anti-inflammatory drug Fenclorac from phenyl cyclohexane.

How could you convert butanenitrile into the following compounds?

Write each step showing the reagents needed.

(a) 1-Butanol

(b) Butylamine

(c) 2-Methyl-3-hexanone

Predict the product and provide the mechanism for each reaction below.
See all solutions

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