Single Choice

An alcohol gave Lucas test in about 5 minutes. When the alcohol was treated with hot concentrated $$H_2SO_4$$, it gave an alkene of molecular formula $$C_4H_8$$ which on ozonolysis gives single product with molecular formula $$C_2H_4O$$. The structure of alcohol is:

A$$CH_3CH(OH)CH_2CH_2CH_3$$
B$$CH_3CH_2CH_2CH_2OH$$
C$$CH_3CH(OH)CH_2CH_3$$
Correct Answer
D$$(CH_3)_3C-OH$$

Solution


CH3CH2−CH(OH)−CH3−→−H+CH3−CH=CH−CH3−→−−−−−−O3,Zn/H2O2CH3−CHOCH3CH2−CH(OH)−CH3→H+CH3−CH=CH−CH3→O3,Zn/H2O2CH3−CHO

As Lucas test is given by compound in about 5 minutes, it is a secondary alcohol.

After ozonolysis only one product is obtained confirms that the alkene form was symmetric and that is possible if and only if alcohol was secondary.

Hence, the alcohol is CH3CH(OH)CH2CH3CH3CH(OH)CH2CH3 .

SIMILAR QUESTIONS

Alcohols, Phenols and Ethers

An unknown alcohol is treated with the 'Lucas reagent' to determine whether the alcohol is primary, secondary or tertiary. Which alcohol reacts fastest and by what mechanism?

Alcohols, Phenols and Ethers

From amongst the following alcohols the one that would react fastest with conc. $$HCl$$ and anhydrous $${Z}n{C}l_{2}$$, is:

Alcohols, Phenols and Ethers

Lucas test is given by an alcohol within 5 minutes. 0.22 g of which liberates 56 mL of $$ CH_4$$ at STP on treating with $$CH_3MgI$$.The structure of alcohol is:

Alcohols, Phenols and Ethers

Which of the following compounds reacts immediately with Lucas reagent?

Alcohols, Phenols and Ethers

Which alcohol will give immediate turbidity on shaking with HCl at room temperature?

Alcohols, Phenols and Ethers

An alcohol (A) gives Lucas test within 5 min. 7.4 g of alcohol when treated with sodium metal liberates 1120 mL of $$H_2$$ at STP. What will be alcohol (A)?

Alcohols, Phenols and Ethers

Which of the following alcohols reacts most readily with Lucas reagent?

Alcohols, Phenols and Ethers

Vinyl chloride and ethyl chloride can be distinguished by:

Alcohols, Phenols and Ethers

Which of the following will react fastest with Lucas reagent?

Alcohols, Phenols and Ethers

Explain the following behavior: Reactivity of all the three classes of alcohols with conc. HCl and $$ZnCl_2$$ is different.

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