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Structural and Physical Properties of Carbonyls

Compound 'A' ...

Question

Compound ' $A$ ' (molecular formula $C_{3} H_{8} O$ is treated with acidified potassium dichromate to form a product ' $B$ ' (molecular formula $C_{3} H_{6} O$ ). ' $B$ ' forms a shining silver mirror on warming with ammoniacal silver nitrate. ' $B$ ' when treated with an aqueous solution of $H_{2} N C O N H N H_{2}$ and sodium acetate gives a product ' $C$ '. Identify the structure of ' $C$ '.

C H_{3} C H_{2} C H = N N H C O N H_{2}

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C H_{3} C H_{2} O H + N C O N H N H_{2}

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Solution

The correct option is A $C H_{3} C H_{2} C H = N N H C O N H_{2}$
$A$ is an alcohol and its oxidation product gives positive Tollen's test, i.e. $B$ must be an aldehyde $(C H_{3} C H_{2} C H O) .$

$C H_{3} C H_{2} C H_{2} O H (A) K_{2} C r_{2} O_{7} / H^{+} - ------- \to C H_{3} C H_{2} C H O (B)$

$C H_{3} C H_{2} C H O (B) + H_{2} N H N C O N H_{2} (semicarbazide) \to C H_{3} C H_{2} C H = N N H C O N H_{2} (C)$

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Similar questions

(A)

C_{3} H_{8} O

C_{3} H_{6} O

H_{2} N C O N H N H_{2} \cdot H C l

^{'} A^{'}

C_{3} H_{8} O

^{'} B^{'}

C_{3} H_{6} O

^{'} B^{'}

^{'} B^{'}

N H_{2} C O N H N H_{2}, H C l

^{'} C^{'}

^{'} C^{'}

A

C_{3} H_{8} O

B

C_{3} H_{6} O

B

B

H_{2} N C O N H {N H}_{2} . H C l

C

C

(X)

C_{3} H_{8} O

(Y)

C_{3} H_{6} O

(Y)

A g N O_{3}

(Y)

N H_{2} C O N H N H_{2}

H C l

(Z)

(Z)

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