Alcohols and Ethers - Result Question 32

####35. Statement I Solubility of n-alcohol in water decreases with increase in molecular weight.

Statement II The relative proportion of the hydrocarbon part in alcohols increases with increasing molecular weight which permit enhanced hydrogen bonding with water.

(1988,2M)

Passage Based Questions

Passage 1

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on reaction with KOH gives only M.

(2008,3×4M=12M)

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Answer:

Correct Answer: 35. secondary

Solution:

  1. ROH Hydrophilic

Hydrophobic

Increasing molecular weight increases hydrocarbon (R) proportion that lowers the solubility in water.

Passage 1

Compound J must be benzaldehyde because it on treatment with KOH undergoing Cannizzaro’s reaction producing benzyl alcohol and pot-benzoate (L).

C6H5CHOKOHC6H5CH2OH benzyl alcohol +C6H5COOK(L)

Also M is aldol condensation product formed from acetophenone

acetophenone (K)

I=PhH3CC=CHPh

and H=PhOCH3 3-alcohol CH2Ph



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