[figure] The correct sequence of reagents for the above conversion of X to Y is :
- (i) NaOH(aq), (ii) Jones reagent, (iii) H3O+
- (i) NaOEt, (ii) B2H6/H2O2, (iii) Jones reagent
- (i) Jones reagent, (ii) NaOEt, (iii) Hot KMnO4/KOH
- (i) B2H6/H2O2, (ii) NaOEt, (iii) Jones reagent
Answer
(2) (i) NaOEt, (ii) B2H6/H2O2, (iii) Jones reagent
Solution
X is 1-bromo-1-phenylethane; in Y the oxygen function is on the terminal carbon, so an anti-Markovnikov route is needed:
[figure]
(i) NaOEt (strong base): dehydrobromination gives styrene, C6H5CH=CH2
(ii) B2H6/H2O2 (hydroboration–oxidation): anti-Markovnikov addition of water gives 2-phenylethanol, C6H5CH2CH2OH
(iii) Jones reagent (CrO3/H2SO4): oxidises the 1° alcohol to phenylacetic acid, C6H5CH2COOH (Y)
Option (1) puts –OH on the benzylic carbon (Jones reagent then gives a ketone), in option (3) Jones reagent cannot act on the alkyl halide, and in option (4) B2H6 cannot act on an alkyl halide.
Answer: (2)