CameraIcon

SearchIcon

MyQuestionIcon

1

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

Stereoisomerism

An organic co...

Question

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 $C$ .

Open in App

Solution

1-phenyl-3-methyl-pent-1-yne (compound A, optically active) reacts with dil alkaline $K M n O_{4}$ solution to form 2-methyl butanoic acid (compound B, optically active) and benzoic acid (compound C, optically inactive). Th decarboxylation of benzoic acid with sodalime gives benzene.
The decarboxylation of 2-methyl butanoic acid with sodalime gives butane which is optically inactive .

Suggest Corrections

thumbs-up

0

Similar questions

Q. 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.

Q. An organic compound

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

B r_{2}

in presence of phosphorus to produce

B

which can be resolved into enantiomers.

B

on dehydrobromination yields

C (C_{5} H_{8} O_{2})

which does not show stereoisomerism.

C

on decarboxylation gives an alkene which on further ozonolysis gives

D

E

D

gives Schiff's test but

E

does not. The correct identity of these compounds are:

Q. An organic acid

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

B r_{2}

in presence of phosphorus to produce a resolvable compound B. B on dehydrobromination yields C. C does not show geometrical isomerism and on decarboxylation gives an alkene D. D on ozonolysis gives E and F. Compound E gives positive Schiff's test but F does not. Give structures of A to F.

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

A

on refluxing with aqueous

H I

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

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. 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.

View More

Join BYJU'S Learning Program

similar_icon

Related Videos

lock

Introduction

CHEMISTRY

Watch in App

explore_more_icon

Explore more

Stereoisomerism

Standard XII Chemistry

Join BYJU'S Learning Program

CrossIcon