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

Byju's Answer

Standard XII

Chemistry

Halogenation of Alpha Carbon

Compound C 8 ...

Question

Compound $C_{8} H_{9} C l$ (A) on treatment with $K C N$ followed by hydrolysis gives $C_{9} H_{10} O_{2}$ (B). Ammonium salt of (B) on dry distillation gives (C), which reacts with alkaline solution of bromine to give $C_{8} H_{11} N$ (D). Another compound (E), is obtained by the action of nitrous acid on (D) or by the action of aqueous potash on (A). (E) on oxidation gives $C_{8} H_{6} O_{4}$ (F) which gives an anhydride $C_{8} H_{4} O_{3}$ (G) on heating.

If x is the DOE of (G) and y is the DOE of (F), then x-y=

Open in App

Solution

Since the ratio of carbon to hydrogen in (A) is almost 1:1, it should be benzenoid.

Since (A) reacts with $K C N$ , it should have either a $- C H_{2} C l$ or a $- C H_{2} - C H_{2} - C l$ group. The reacon as to why $- C H_{2} - C H_{2} - C l$ is not the required substituent because later we get an anhydride which means that a methyl group should be oxidised to carboxylic acid.

Suggest Corrections

Similar questions

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) gives positive Liebermann reaction and on treatment with

C H C l_{3} / K O H

followed by hydrolysis gives (B) and (C) ,. Compound (B) gives colour with Schiff's reagent but not (C), which is steam - volatile. (C) on treatment with

L I A l H_{4}

gives (D),

C_{7} H_{8} O_{2}

which on oxidation gives 9E), Compound (E) reacts with

{(C H_{3} C O)}_{2} O / C H_{3} C O O H

to give a pain - reliever (F), Give structure of (A) to (F) with proper reasoning.

Q. An alcohol

(A)

on dehydration gives

(B)

which adds bromine molecule to give

(C)

(C)

on heating with sodamide gives

(D)

which on hydration in the presence of

H g^{+ +} / H_{2} S O_{4}

gives

(E)

E

on reduction by lithium aluminium hydride gives

(A)

(E)

is also obtained on dry distillation of calcium salt of acetic acid. How many enolisable proton present in the product

(E)

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]

. Oxidation of

[B]

with acidified potassium dichromate also gives

[D]

Identify

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

and

[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