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Chemical Properties of Ethers

Allanite want...

Question

Allanite wanted to prepare (R) 2-Methoxy butane using Williamson ether synthesis. He remembered that Williamson synthesis involves a $S_{N} 2$ displacement, which takes place with inversion of configuration. He ordered a bottle of (S) 2-Butanol for his chiral starting material. He also remembered that the $S_{N} 2$ goes best on primary halides so he made methyl halide and sodium (S) 2-butoxide after warming these reagents together he obtained an excellent yield of 2-Methoxy butane.

2-Methoxy butane $a n h y d r o u s H I - ------- \to$ products

Products formed are:

H_{3} C - I + C H_{3} - (O H) C H - C H_{2} - C H_{3}

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C H_{3} - I + C H_{3} - C H_{2} - C H_{2} - C H_{3}

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C H_{3} - O H + C H_{3} - C H (I) - C H_{2} - C H_{3}

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C H_{3} - C H_{2} - I + C H_{3} - (O H) C H - C H_{3}

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Solution

The correct option is D $C H_{3} - O H + C H_{3} - C H (I) - C H_{2} - C H_{3}$
2-Methoxy butane reacts with anhydrous HI to form methanol and 2-butanol. The products are as shown.

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