QUESTION 4 Consider the following reaction where Compounds (A) and (B) are hydrocarbons. (A) + n-Propyl bromide NaNH, NH3 (B) (i) Catalytic hydrogenation of Compound (A) in the presence of Lindlar's catalyst gives Compound (C) (a hydrocarbon). (ii) Dehydrobromination of Compounds (D) and (E) gives the same Compound (C) which can regenerate Com- pound (D) and Compound (E) by the addition of HBr in the presence and absence of peroxide, respectively. (iii) Reaction of Compound (C) with benzene in presence of H+ leads to formation of 1,1-diphenylethane. (iv) Compound (B) when treated with lithium in liquid ammonia followed by quenching with NH4Cl gives a stereoisomer (F). Identify the Compounds (A) to (F). 2

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QUESTION 4
Consider the following reaction where Compounds (A) and (B) are hydrocarbons.
(A) + n-Propyl bromide
NaNH,
NH3
(B)
(i) Catalytic hydrogenation of Compound (A) in the presence
of Lindlar's catalyst gives Compound (C) (a hydrocarbon).
(ii) Dehydrobromination of Compounds (D) and (E) gives
the same Compound (C) which can regenerate Com-
pound (D) and Compound (E) by the addition of HBr in
the presence and absence of peroxide, respectively.
(iii) Reaction of Compound (C) with benzene in presence of
H+ leads to formation of 1,1-diphenylethane.
(iv) Compound (B) when treated with lithium in liquid
ammonia followed by quenching with NH4Cl gives a
stereoisomer (F).
Identify the Compounds (A) to (F).
2
Transcribed Image Text:QUESTION 4 Consider the following reaction where Compounds (A) and (B) are hydrocarbons. (A) + n-Propyl bromide NaNH, NH3 (B) (i) Catalytic hydrogenation of Compound (A) in the presence of Lindlar's catalyst gives Compound (C) (a hydrocarbon). (ii) Dehydrobromination of Compounds (D) and (E) gives the same Compound (C) which can regenerate Com- pound (D) and Compound (E) by the addition of HBr in the presence and absence of peroxide, respectively. (iii) Reaction of Compound (C) with benzene in presence of H+ leads to formation of 1,1-diphenylethane. (iv) Compound (B) when treated with lithium in liquid ammonia followed by quenching with NH4Cl gives a stereoisomer (F). Identify the Compounds (A) to (F). 2
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