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(a) Carry out the following conversions ...

(a) Carry out the following conversions :
(i) pnitrotoluene to 2-bromobenzoic acid
(iii) Propanoic acid to acetic acid
(b)An alkene with molecular formula `C_5H_10` on ozonolysis gives a mixture of two compound B and C .Compound B gives positive Fehling test and also reacts with iodine and NaOH solution. Compound C does not give Fehling solution test but forms iodoform. Identify the compounds A, B and C.

Text Solution

Verified by Experts

P-nitrotolune to 2-bromobenzoic acid:

(ii) Propanoic acid to acetic acid : `CH_3CH_2COOH+NaOHrarrCH_3CH_2COONa+H_2O`
`CH_3CH_2COONa+NaOHoverset(CaO)rarr C_2H_6+Na_2CO_3`
`C_2H_6+K_2Cr_2O_7rarr CH_3COOH`
`CH_3-CH=underset(CH_(3))underset(|)C-CH_3underset((ii) Zn//H_2O)overset((i)O_3)rarr H_2C-CHO+O=underset(CH_3)underset(|)C-CH_3`
Since ,compound B gives Fehling's test therefore ,it must be aldehyde .Further since aldehyde 'B' gives iodoform on treatment with `l_2` and NaOH therefore ,it must be aldehyde .Further since aldehye 'B' must be acetadehyde `(CH_3CHO)`
Since 'C' does not give fehling test it must be a ketone further
Since ketone 'C' contian three carbon atoms and gives iodoform on treatment with `I_2` and NaOH
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