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Curtius and Hofmann Rearrangements

Show how each...

Question

Show how each of the following compounds can be converted to benzoic acid.

(i) Ethylbenzene (ii) Acetophenone

(iii) Bromobenzene (iv) Phenylethene (Styrene)

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Solution

(i)

(ii)

(iii)

(iv)

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2

Give simple chemical tests to distinguish between the following pairs of compounds.

(i) Propanal and Propanone

(ii) Acetophenone and Benzophenone

(iii) Phenol and Benzoic acid

(iv) Benzoic acid and Ethyl benzoate

(v) Pentan-2-one and Pentan-3-one

(vi) Benzaldehyde and Acetophenone

(vii) Ethanal and Propanal

p K_{a}

C H_{3} C O O H

How will you bring about the following conversions in not more than two steps?

(i) Propanone to Propene

(ii) Benzoic acid to Benzaldehyde

(iii) Ethanol to 3-Hydroxybutanal

(iv) Benzene to m-Nitroacetophenone

(v) Benzaldehyde to Benzophenone

(vi) Bromobenzene to 1-Phenylethanol

(vii) Benzaldehyde to 3-Phenylpropan-1-ol

(viii) Benazaldehyde to α-Hydroxyphenylacetic acid

(ix) Benzoic acid to m- Nitrobenzyl alcohol

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