Question

Which is the most suitable reagent for the following
conversion?
O
||
CH₃ —CH= CH—CH₂ —C—CH₃ →
O
||
CH₃ —CH = CH—CH₂ —C—OH
(a) Tollen's reagent (b) Benzoyl peroxide
(c) I2 and NaOH solution (d) Sn and NaOH solution

Answer 1

Which is the most suitable reagent for the following

conversion?

O

||

CH₃ —CH= CH—CH₂ —C—CH₃ →

O

||

CH₃ —CH = CH—CH₂ —C—OH

(a) Tollen's reagent

(b) Benzoyl peroxide

(c) I2 and NaOH solution

(d) Sn and NaOH solution

Answer 2

I2 and NaOH solution is the correct option.

Explanation:

• The reactant given here is a ketone.

• The ketone needs to be changed to carboxylic acid.

• This needs a haloform reaction to be done.

• We know that haloform reaction needs a carbonyl group for it's work.

• The carbonyl group also needs to have alpha methyl group for the reaction to occur.

• As the Iodoform is formed from the product, the left over reactant is oxidised to carboxylic acid.

For more information about the haloform reaction,

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A ketone A which undergoes haloform reaction gives a compound B on reduction . B on heating with sulphuric acid gives a compound C which forms monoozonide D. D onhydrolysis in the presence of zinc dust gives only acetaldehyde. identify A, B, C, and D. write down the reactions involved.