2-Methyloxirane (propylene oxide) is treated separately with (I) CH3ONa in CH3OH, and (II) CH3OH with a catalytic amount of H2SO4. The major products are, respectively,

(I) 1-methoxypropan-2-ol; (II) 2-methoxypropan-1-ol

(I) 1-methoxypropan-2-ol; (II) 1-methoxypropan-2-ol

(I) 2-methoxypropan-1-ol; (II) 1-methoxypropan-2-ol

(I) 2-methoxypropan-1-ol; (II) 2-methoxypropan-1-ol

(I) 1-methoxypropan-2-ol; (II) 2-methoxypropan-1-ol

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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap014

2-Methyloxirane (propylene oxide) is treated separately with (I) $CH X_{3} ONa$ in $CH X_{3} OH$ , and (II) $CH X_{3} OH$ with a catalytic amount of $H X_{2} SO X_{4}$ . The major products are, respectively,

A(I) 1-methoxypropan-2-ol; (II) 1-methoxypropan-2-ol
B(I) 2-methoxypropan-1-ol; (II) 1-methoxypropan-2-ol
C(I) 2-methoxypropan-1-ol; (II) 2-methoxypropan-1-ol
D(I) 1-methoxypropan-2-ol; (II) 2-methoxypropan-1-ol

Answer: D

Under basic conditions the strong nucleophile

CH X_{3} O X^{-}

attacks the less hindered carbon (SN2), giving 1-methoxypropan-2-ol. Under acid catalysis the protonated epoxide has considerable positive charge on the more substituted carbon, so methanol attacks there, giving 2-methoxypropan-1-ol.

Practice Alcohols, Phenols and Ethers More on Preparation of alcohols including from carbonyls and Grignard

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2-Methyloxirane (propylene oxide) is treated separately with (I) CHX3​ONa in CHX3​OH, and (II) CHX3​OH with a catalytic amount of HX2​SOX4​. The major products are, respectively,

Answer: D

More questions on Preparation of alcohols including from carbonyls and Grignard

2-Methyloxirane (propylene oxide) is treated separately with (I) $CH X_{3} ONa$ in $CH X_{3} OH$ , and (II) $CH X_{3} OH$ with a catalytic amount of $H X_{2} SO X_{4}$ . The major products are, respectively,