a) What happens when — i) Methyl bromide is treated with sodium in presence of dry ether? ii) Ethyl acetate is hydrolysed in presence of acid? (1 + 1) b) Write the structures of compounds whose IUPAC names are as follows: i) 2-Butanol ii) N, N-dimethyl methanamine iii) 2-Aminotol

Question

a) What happens when — i) Methyl bromide is treated with sodium in presence of dry ether? ii) Ethyl acetate is hydrolysed in presence of acid? (1 + 1) b) Write the structures of compounds whose IUPAC names are as follows: i) 2-Butanol ii) N, N-dimethyl methanamine iii) 2-Aminotoluene (1 + 1 + 1)

Accepted Answer

>

> [!TLDR]
> (a) Wurtz gives ethane; acid hydrolysis of the ester gives acid + alcohol. (b) Structures drawn for 2-butanol, trimethylamine and o-toluidine.
>
> (a) Reactions:
>
> (i) Methyl bromide with sodium in dry ether — this is the Wurtz reaction, in which two alkyl halide molecules couple to give a higher (symmetrical) alkane:
> 2CH3Br + 2Na --dry ether--> CH3-CH3 (ethane) + 2NaBr
> Product: ethane.
>
> (ii) Hydrolysis of ethyl acetate in the presence of acid — the ester is cleaved to give back the parent carboxylic acid and alcohol (reverse of esterification):
> CH3COOC2H5 + H2O --H+--> CH3COOH (acetic acid) + C2H5OH (ethanol)
>
> (b) Structures from IUPAC names:
>
> (i) 2-Butanol (butan-2-ol) — a 4-carbon chain with -OH on C-2:
> CH3-CH(OH)-CH2-CH3
>
> (ii) N,N-dimethylmethanamine — methanamine (CH3NH2) with both N-hydrogens replaced by methyl groups, i.e. trimethylamine:
> (CH3)3N   [CH3-N(CH3)-CH3]
> …

Q.a) What happens when — i) Methyl bromide is treated with sodium in presence of dry ether? ii) Ethyl acetate is hydrolysed in presence of acid? (1 + 1) b) Write the structures of compounds whose IUPAC names are as follows: i) 2-Butanol ii) N, N-dimethyl methanamine iii) 2-Aminotoluene (1 + 1 + 1)

Concept understanding — Nomenclature of Haloalkanes and Haloarenes

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