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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

How could you convert butanoic acid into the following compounds?

Write each step showing the reagents needed.

(a) 1-Butanol

(b) 1-Bromobutane

(c) Pentanoic acid

(d) 1-Butene

(e) Octane

How could you convert butanoic acid into the following compounds?
Write each step showing the reagents needed.
(a) 1-Butanol (b) 1-Bromobutane (c) Pentanoic acid
(d) 1-Butene (e) Octane

Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound

a. Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrins that results

b. Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms

How would you prepare the following carboxylic acids?

(a)(CH3)3CCO2Hfrom(CH3)3CCI

(b) CH3CH2CH2CO2HfromCH3CH2CH2Br

How might you carry out the following transformation? More than one step

is needed.
See all solutions

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