Q.(i) Identify the major organic products in each of the following reactions:

Each scheme is a named substitution/addition reaction (Finkelstein, peroxide/anti-Markovnikov HBr addition, Hunsdiecker, benzylic SN1 chlorination); SOCl$_2$ is preferred for alcohol→chloride because its by-products leave as gases.

(i) Identifying products:

(x) $CH_3CH_2CH_2Cl + NaI \xrightarrow[\text{heat}]{\text{acetone}} CH_3CH_2CH_2I\ (A) + NaCl\downarrow$ — the Finkelstein reaction; NaCl precipitates out of acetone (NaI is soluble, NaCl is not), driving the substitution forward.

(v) $Ph\text{-}CH_2\text{-}CH{=}CH_2 + HBr \xrightarrow{\text{peroxide}} Ph\text{-}CH_2\text{-}CH_2\text{-}CH_2Br\ (B)$ — free-radical addition (Kharasch/peroxide effect) gives the anti-Markovnikov product, with Br on the terminal carbon.

And $CH_3COOAg + Br_2 \xrightarrow[CCl_4]{\text{distillation}} CH_3Br\ (C) + AgBr\downarrow + CO_2\uparrow$ — the Hunsdiecker reaction, a decarboxylative halogenation that shortens the chain by one carbon.

(z) $HO\text{-}C_6H_4\text{-}CH_2OH + HCl \xrightarrow{\Delta} HO\text{-}C_6H_4\text{-}CH_2Cl\ (D)$ — the benzylic -CH$_2$OH is converted to -CH$_2$Cl via an S$_N$1 mechanism (the benzylic carbocation is resonance-stabilised), while the phenolic -OH is unreactive toward HCl (phenols don't form aryl halides this way, since the ring C–O bond has partial double-bond character from resonance).

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