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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

20-36 Order the compounds in each of the following sets with respect to increasing acidity:

(a) Acetic acid, oxalic acid, formic acid

(b) p-Bromobenzoic acid, p-nitrobenzoic acid, 2,4-dinitrobenzoic acid

(c) Fluoroacetic acid, 3-fluoropropanoic acid, iodoacetic acid

Propose structures for carboxylic acids that show the following peaks in their 13C NMR spectra. Assume that the kinds of carbons (1°, 2°, 3°, or 4°) have been assigned by DEPT-NMR.

a)C7H12O2,25.5δ(20),25.9δ(20),29δ(20),43.1δ(30),183δ(40)b)C8H8O2,21.4δ(1o),128.3δ(4o),129δ(3o),129.7δ(3o),143.1δ(4o),168.2δ(4o)

Pregabalin, marketed as Lyrica, is an anticonvulsant drug that is also effective in treating chronic pain. The IUPAC name of pregabalin is (S)-3-(aminomethyl)-5-methylhexanoic acid.(An aminomethyl group is -CH3NH2.) Draw the structure of pregabalin.

Which would you expect to be a stronger acid, the lactic acid found in tired muscles or acetic acid? Explain.

Cyclopentanecarboxylic acid and 4-hydroxycyclohexanone have the

same formula (C6H10O2), and both contain an -OH and a C=O group. How could

you distinguish between them using IR spectroscopy?
See all solutions

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