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Question of 135

Q.How can these conversions be done ? Give chemical equations only.

(i) Propan-2-ol from propene
(ii) Benzyl alcohol from benzyl chloride
(iii) Propan-1-ol from ethyl magnesium chloride
(iv) 2-methyl propan-2-ol from methyl magnesium bromide
(v) Picric acid from phenol OR How will you synthesize the following ? Give chemical equations only.
(i) 1-phenylethanol from a suitable alkene
(ii) Cyclohexylmethanol with the help of alkyl halide by SN2S_N2 reaction.
(iii) Pentan-1-ol from a suitable alkyl halide.
Uttar Pradesh UpmspUP Board (UPMSP) Intermediate 2025Subjective· 5mImportance★★★★★
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Five one-step conversions: acid hydration, alkaline hydrolysis, two Grignard additions and a nitration, giving propan-2-ol, benzyl alcohol, propan-1-ol, 2-methylpropan-2-ol and picric acid.

  1. Propan-2-ol from propene — acid-catalysed (Markovnikov) hydration; –OH adds to the more substituted carbon: CH3−CH=CH2+H2O→H+CH3−CH(OH)−CH3 (propan-2-ol)CH_3{-}CH{=}CH_2 + H_2O \xrightarrow{H^+} CH_3{-}CH(OH){-}CH_3\ \text{(propan-2-ol)}
  2. Benzyl alcohol from benzyl chloride — hydrolysis with aqueous alkali: C6H5CH2Cl+NaOH(aq)→ΔC6H5CH2OH+NaClC_6H_5CH_2Cl + NaOH_{(aq)} \xrightarrow{\Delta} C_6H_5CH_2OH + NaCl
  3. Propan-1-ol from ethyl magnesium chloride — Grignard reagent + methanal (HCHO) gives a primary alcohol: C2H5MgCl+HCHO→C2H5−CH2−OMgCl→H3O+CH3CH2CH2OH (propan-1-ol)C_2H_5MgCl + HCHO \rightarrow C_2H_5{-}CH_2{-}OMgCl \xrightarrow{H_3O^+} CH_3CH_2CH_2OH\ \text{(propan-1-ol)}
  4. 2-methylpropan-2-ol from methyl magnesium bromide — Grignard reagent + a ketone (propanone) gives a tertiary alcohol: CH3COCH3+CH3MgBr→(CH3)3C−OMgBr→H3O+(CH3)3C−OH (2-methylpropan-2-ol)CH_3COCH_3 + CH_3MgBr \rightarrow (CH_3)_3C{-}OMgBr \xrightarrow{H_3O^+} (CH_3)_3C{-}OH\ \text{(2-methylpropan-2-ol)} …

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