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in Haloalkanes and Haloarenes by (34 points)
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What happens when : (Give chemical reactions) 

(i) Cyclohexanol is treated with thionyl chloride 

(ii) \( p \)-hydroxybenzyl alcohol is heated with \( HCl \). 

(iii) Ethyl bromide is refluxed with NaI in acetone. 

(iv) Ethyl bromide is treated with mercurous fluoride.

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(i)

(ii)

(iii)

\(\underset{ethyl \,bromide}{CH_3 - CH_2 -Br} + NaI \xrightarrow{acetone} \underset{ethyl\,iodide}{CH_3 - CH_2 - I }+ NaBr \) 

(iv)

\(\underset{ethyl \, bromide}{2\,CH_3-CH_2 - Br} + \underset{mercurous\,fluoride}{Hg_2 F_2}\longrightarrow \underset{ethyl \,fluoride}{2\,CH_3 - CH_2 - F} + \underset{mercurous\,romide}{Hg_2Br_2}\)

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