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Nucleophilic Addition at the Carbonyl

An organic co...

Question

An organic compound gives hydrogen on reacting with sodium metal. It also gives iodoform test and forms an aldehyde of molecular formula $C_{2} H_{4} O$ on oxidation with acidified dichromate the compound is:

A

C H_{3} O H

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B

C H_{3} C O O H

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C

C H_{3} C H O

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D

C_{2} H_{5} O H

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Solution

The correct option is D $C_{2} H_{5} O H$
The compound is forming $C_{2} H_{4} O$ on oxidation and it is evolving hydrogen gas with sodium metal.

The compound that is formed is ethanal and the given compound is ethanol ( $C_{2} H_{6} O$ ) or $C_{2} H_{5} O H$ which gives positive iodoform test.

$C H_{3} C H_{2} O H + [O] N a_{2} C r_{2} O_{7} / H^{+} - -------- \to C H_{3} C H O + H_{2} O$

Option D is correct.

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Similar questions

Q. An organic compound 'X' with molecular formula C2H6O, on oxidation with acidified potassium dichromate gives ethanoic acid. What is the compound 'X'?

Q. An organic compound

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having molecular formula

C_{2} H_{7} N

on treatment with nitrous acid gives a compound

[B]

having molecular formula

C_{2} H_{6} O

[B]

on treatment with an organic compound

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gives a carboxylic acid

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[B]

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having molecular formula

C_{3} H_{8} O

, gives positive iodoform test. On oxidation with acidified

K_{2} C r_{2} O_{7}

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[A]

having molecular formula

C_{2} H_{7} N

on treatment with nitrous acid gives a compound

[B]

having molecular formula

C_{2} H_{6} O

[B]

on treatment with an organic compound

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An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of the compound is 86. It does not reduce Tollen's reagent but forms an addition compound with sodium hydrogen sulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible sturcture of the compound.

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