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

Byju's Answer

Standard XII

Chemistry

Decarboxylation

An organic co...

Question

An organic compound contains C, H and O, and its aqueous solution is neutral. 1.44 g of A on refluxing with dilute $H_{2} S O_{4}$ produces two organic compounds B and C of which the only B is resolvable and gives effervescence with $N a H C O_{3}$ . Also, neutralization of entire B requires 0.4 g of $N a O H$ . B on reduction with HI/red phosphorus produces a hydrocarbon D which is non-resolvable. Also D on monochlorination yield three alkyl halide in which the only one is resolvable. Deduce structures of A to D.

Open in App

Solution

Step 1- Hydrolysis in the acidic medium of compound $A$ will in acid $(B)$ and alcohol
Step 2- In the presence of strong reducing agent Red phosphorus and $H I$ compound $B$ will convert in $C$ ( $3 -$ Methylpentane)

Suggest Corrections

Similar questions

Q. An organic compound A has molecular formula

C_{12} H_{14}

and it can be resolved into enantiomers. Compound

A

on boiling with dilute alkaline

K M n O_{4}

solution yield

B (C_{5} H_{10} O_{2})

and a white crystalline substance

C

. Compound

C

on treatment with sodalime produced benzene. Compound B is still resolvable but decarboxylation of

B

with sodalime renders it non-resolvable. Deduce structures of

A, B

and

C

Q. A monobasic acid A has neutralization equivalent 116 and does not decolorize Bayer's regent. Also, A is enantiomeric. A on treatment with

B r_{2} / r e d

phosphorus produces B which is still resolvable. B on dehydrobromination produced C which shows stereoisomerism C on decarboxylation produced. D which does not show stereoisomerism. Deduce structures of A, B, C, and D.

Q. An organic compound

A

has molecular formula

C_{5} H_{10} O

and it neither decolourise bromine water solution nor evolve any gas on heating with

N a

-metal.

A

on refluxing with aqueous

H I

yields

B (C_{5} H_{10} I_{2})

which is non-resolvable.

B

on treatment with

N a C N

in acetone yield

C (C_{5} H_{10} I N)

in significant amount while

B

on treatment with aqueous

H_{2} O

yields

D (C_{5} H_{11} I O)

in significant amount.

D

does not change the orange colour of acidic dichromate solution. Deduce structures of

A

D

Q. An organic compound has molecular formula A

(C_{7} H_{10})

and known to decolourized

B r_{2}

-water solution.A on reduction with

H_{2} / P t

produces B

(C_{7} H_{14})

. B on monochlorination with

C l_{2} / h v

produces four isomeric monochloro derivatives

C_{7} H_{13} C l

. A on ozonolysis followed by work-up with Zn-dimethyl sulphide affords two and only two products, one being methanal and other C

(C_{6} H_{8} O_{3})

. C is oxidised with acidic solution of dochromate to yields D

(C_{6} H_{8} O_{5})

which is soluble in

N a H C O_{3}

. D is reduced with

N a B H_{4}

to yield E

(C_{6} H_{10} O_{3})

which may be resolved into enantiomers. Identify A to E.

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

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.

Join BYJU'S Learning Program

Step 1- Hydrolysis in the acidic medium of compound A will in acid (B) and alcoholStep 2- In the presence of strong reducing agent Red phosphorus and HI compound B will convert in C( 3−Methylpentane)

Step 1- Hydrolysis in the acidic medium of compound $A$ will in acid $(B)$ and alcohol
Step 2- In the presence of strong reducing agent Red phosphorus and $H I$ compound $B$ will convert in $C$ ( $3 -$ Methylpentane)