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Friedel Crafts Alkylation, Acylation

The reaction ...

Question

The reaction of compound P with $C H_{3} M g B r$ (excess) in $(C_{2} H_{5})_{2} O$ followed by addition of $H_{2} O$ gives Q. The compound Q on treatment with $H_{2} S O_{4}$ at $0^{\circ} C$ gives R. The reaction of R with $C H_{3} C O C l$ in the presence of anhydrous $A l C l_{3}$ in $C H_{2} C l_{2}$ followed by treatment with $H_{2} O$ produces compound S [Et in compound P is ethyl group]

The product S is:

A

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B

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C

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D

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Solution

The correct option is A

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Q. The reaction of compound P with

C H_{3} M g B r

(C_{2} H_{5})_{2} O

followed by addition of

H_{2} O

gives Q. The compound Q on treatment with

H_{2} S O_{4}

0^{\circ} C

gives R. The reaction of R with

C H_{3} C O C l

in the presence of anhydrous

A l C l_{3}

C H_{2} C l_{2}

followed by treatment with

H_{2} O

produces compound S [Et in compound P is ethyl group]

The reactions, Q to R and R to S, are:

Q. Treatment of compound O with

K M n O_{4} / H^{+}

gave P, which on heating with ammonia gave Q. The compound Q on treatment with

B r_{2} / N a O H

produced R. On strong heating, Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of

K O H

followed by acidification, gave a compound T.

The compound R is:

Q. Treatment of benzene with

C O / H C l

in the presence of anhydrous

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

followed by reaction with

A c_{2} O / N a O A c

gives compound X as the major product. Compound X upon reaction with

B r_{2} / N a_{2} C O_{3}

, followed by heating at 473 K with moist

K O H

furnishes Y as the major product. Reaction of X with

H_{2} / P d - C,

H_{3} P O_{4}

treatment gives Z as the major product.
The compound Y is:

Q. Treatment of compound O with

K M n O_{4} / H^{+}

gave P, which on heating with ammonia gave Q. The compound Q on treatment with

B r_{2} / N a O H

produced R. On strong heating, Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of

K O H

followed by acidification, gave a compound T.

The compound T is:

Q. An organic compound (A),

C_{8} H_{4} O_{3}

in dry benzene in the presence of anhydrous

{A l C l}_{3}

gives compound (B). The compound (B) on treatment with

{P C l}_{5}

followed by reaction with

H_{2} / P d ({B a S O}_{4})

gives compound (C) which on reaction with hydrazine gives a cyclised compound (D)

(C_{14} H_{10} N_{2})

. Identify (A), (B), (C), and (D). Explain the formation of (D) from (C).

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