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JIPMER 2019
Exam
JIPMER
Year
2019
Subject
Chemistry
Chapter
Alcohols Phenols and Ethers

JIPMER 2019 · Chemistry · Alcohols Phenols and Ethers

array r CH_3-CH_2-CH=CH_2 X CH_3 CH_2-CH_2-CH_2 OH array What is...

CH3−CH2−CH=CH2→XCH3CH2−CH2−CH2OH\begin{array}{r}\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}=\mathrm{CH}_2 \xrightarrow{\mathrm{X}} \\ \mathrm{CH}_3 \mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}_2 \mathrm{OH}\end{array} What is suitable reagent (X)(\mathrm{X}) ?

Options

  1. AH2∣Pt\mathrm{H}_2 \mid \mathrm{Pt}
  2. BB2H6∣THF,H2O2∣OH−\mathrm{B}_2 \mathrm{H}_6\left|\mathrm{THF}, \mathrm{H}_2 \mathrm{O}_2\right| \mathrm{OH}^{-}
  3. CBr2∣HCl\mathrm{Br}_2 \mid \mathrm{HCl}
  4. DHBr∣H2O2\mathrm{HBr} \mid \mathrm{H}_2 \mathrm{O}_2

Correct answer

B. B2H6∣THF,H2O2∣OH−\mathrm{B}_2 \mathrm{H}_6\left|\mathrm{THF}, \mathrm{H}_2 \mathrm{O}_2\right| \mathrm{OH}^{-}

Step-by-step solution

The suitable reagent x for the conversion, CH3CH2CH Butene =CH2→XCH3CH2CH2CH2OH Butanol \underset{\text{ Butene }}{\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}}=\mathrm{CH}_2 \xrightarrow{\mathrm{X}} \underset{\text{ Butanol }}{\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH}} is B2H6∣THF,H2O2∣OH\mathrm{B}_2 \mathrm{H}_6\left|\mathrm{THF}, \mathrm{H}_2 \mathrm{O}_2\right| \mathrm{OH}. Alkenes react with diborane (B2H6)\left(\mathrm{B}_2 \mathrm{H}_6\right) in presence of THF or diglyme to form alkyl borane (by hydroboration) which on oxidation gives alcohol. The reaction is known as hydroboration-oxidation reaction.
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