Question

An organic compound of molecular formula C4H10O
does not react with sodium. With excess of HI, it gives only one type of alkyl halide. The compound is (1) Ethoxyethane (2)2- Methoxypropane (3) 1-Methoxypropane (4)1-Butanol.

Answer 1

Answer:

1) Ethoxyethane

Explanation:

The reaction of HI with ethers is called Williamson's ether synthesis

It yields two compounds as product, an alcohol and an alkyl halide.

The carbon chain that gets attached with halogen, is determined by seeing which intermediate is stable or which type of conditions are provided, for e.g. a 3° carbocation intermediate will be the one where halogen gets attached in MAJOR, i.e in minor compound will also be present where you get a OH group attached instead of halogen

However since it is given that only one product is formed, we can conclude that the is in fact one lu one product, instead of major and minor product.

So this ether should be symmetrical so that two products when formed will be identical

And since the options had only one symmetrical ether, yor answer is Ethoxyethane

Hope this answer helped you

Answer 2

The compound is: 1) Ethoxyethane.

- Since it does not react with sodium so it cannot be butanol.

- As the compound gives only one product with excess HI, we can conclude that this should be a symmetrical ether.

- Hence, 2- Methoxypropane and 1-Methoxypropane cannot be the answer.

- So the correct answer is Ethoxyethane and its reaction with HI is given as:

C2H5OC2H5 + 2 HI → 2 C2H5I + H2O