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Arrhenius Bases

An alcohol ...

Question

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 $(E)$ ?

A

2

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B

6

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C

3

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D

0

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Solution

The correct option is B 6
By given hint, it is clear that E is acetone hence overall sequences of reactions will be

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Similar questions

Q. An alcohol A, when heated with concentrated

H_{2} S O_{4}

gives an alkene B. When B is bubbled through bromine water and the product obtained is dehydrohalogenated with excess of sodamide, a new compound C is obtained. The compound C gives D when treated with warm dilute

H_{2} S O_{4}

H g S O_{4}

. D can also be obtained either by oxidising A with

K M n O_{4}

or from acetic acid through its calcium salt. Identify D.

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) 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:

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=

(C_{4} H_{8} O)

, which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives a compound C which forms mono-ozonide D. D on hydrolysis in presence of zinc dust gives only acetaldehyde E. Identify A, B, C, D and E. Write the reactions involved.

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