MyQuestionIcon

1

You visited us 1 times! Enjoying our articles? Unlock Full Access!

Base Catalysed Hydrolysis of Esters

An organic la...

Question

An organic lactum A on acid hydrolysis produces B, an amino acid,.B on treatment with nitrous acid gives C. C on heating with concentrated $H_{2} S O_{4}$ produces a lactone D. A can be synthesized by the reaction of cyclopentanone with hydroxylamine followed by treatment of product with concentrated $H_{2} S O_{4}$ . Deduce structures of A to D.

Open in App

Solution

Product A - Formed by Beckmann Rearrangement
Step 1- Hydrolysis will cause the breaking of the bond between $C = O$ and $N H$ ,
Step 2- On reaction with nitrous acid $O H$ will attach at the place of $N H_{2}$ . It is same as reaction with diazonium salt.
Step 3- Heating with concentrated $H_{2} S O 4$ will form the product D.

Suggest Corrections

thumbs-up

0

Similar questions

Q. An organic compound

A (C_{9} H_{8} O_{3})

does not react with an aqueous solution of

N a H C O_{3}

and does not change the color of litmus paper. A on acid hydrolysis gives

B (C_{9} H_{8} O_{4})

whereas A on treatment with methanol in acid medium gives

C (C_{10} H_{14} O_{4})

as the major alcoholysis product. B on heating with excess of soda-lime produces toluene. Deduce structures of A to C.

Q. A neutral organic compound A has formula

C_{9} H_{16} O_{3}

and rotates plane polarized light. A on acid hydrolysis produces B and

C (C_{3} H_{8} O)

. C on partial oxidation with PCC gives

D (C_{3} H_{6} O)

which does not give iodoform test. D on treatment with dilute solution of

N a O H

E (C_{6} H_{12} O_{2})

which is diastereomeric. E on treatment with the acidic solution of

K M n O_{4}

produces B. Deduce structures of A to E.

Q. Bromobenzene on treatment with fuming

H_{2} S O_{4}

gave a compound which on treatment with

C l_{2} / A l C l_{3}

gives (A). (A) on distillation with dil.

H_{2} S O_{4}

gives (B), (B) on treatment with an eq. of

M g

in dry ether gives (C). (C) on treatment with

C H_{3} C H O

followed by hydrolysis gives (D). (D) on treatment with

N a O I

gives (E). Identify the structures of (A) and (E).

Q. An organic compound (A) on treatment with acetic acid in the presence of sulphuric acid produces an ester (B), (A) on mild oxidation gives (C), (C) with

50 %

potassium hydroxide followed by acidification with dilute hydrochloric acid generates (A) and (D), (D) with phosphorus pentachloride followed by reaction with ammonia gives (E), (E) on dehydration produces hydrocyanic acid. E is an:

Q. An organic compound (A) on treatment with acetic acid in the presence of sulfuric acid produces an ester (B). (A) on mild oxidation gives (C). (C) with 50% KOH followed by acidification with diluted HCI generates (A) and (D). (D) with

{P C I}_{5}

, followed by reaction with ammonia, gives (E). (E) dehydration produces hydrocyanic acid. Identify the compounds (A), (B), (C) (D) and (E). Give chemical equations for the reactions involved :

View More

Join BYJU'S Learning Program

similar_icon

Related Videos

lock

Esters

CHEMISTRY

Watch in App

explore_more_icon

Explore more

Base Catalysed Hydrolysis of Esters

Standard XII Chemistry

Join BYJU'S Learning Program

CrossIcon