CameraIcon

SearchIcon

MyQuestionIcon

1

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

Preparation of Carboxylic Acids

A neutral org...

Question

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 $N a O H$ gives $E (C_{6} H_{12} O_{2})$ which is diastereomeric. E on treatment with the acidic solution of $K M n O_{4}$ produces B. Deduce structures of A to E.

Open in App

Solution

Ester compound on hydrolysis gives alcohol(in this case $p r o p a n - 1 - o l$ ) and Acid.
$P C C$ (pyridinium chlorochromate) will convert or oxidize the primary alcohol into aldehyde
Aldol condensation will give finally the aldol product.

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. 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.

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]

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

[C]

gives a carboxylic acid

[D]

and a sweet smelling compound

[E]

[B]

with acidified potassium dichromate also gives

[D]

[A], [B], [C], [D]

[E]

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

Synthesis of Carboxylic Acids

CHEMISTRY

Watch in App

explore_more_icon

Explore more

Preparation of Carboxylic Acids

Standard XII Chemistry

Join BYJU'S Learning Program

CrossIcon