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Question

(a) Write the chemical reaction involved in Etard reaction.

(b) Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction:

CH3CHO, C6H5COCH3, HCHO

(c) Why is pKa of ClCH2COOH lower than the that of CH3COOH?

(d) Write the product in the following reaction:
CH3CH2CH=CHCH2CN1.(iBu)2AIH−−−−−−−−2.H2O

(e) A and B are two functional isomers of compound C3H6O. On heating with NaOH and I2, isomer A forms yellow precipitate of iodoform whereas isomer B does not form any precipitate. Write the formulae of A and B.

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Solution

(a) Etard reaction:


(b) C6H5COCH3<CH3CHO<HCHO

(c) (i) Due to -I-effect of Cl atom, electron density in the -OH bond in chloroacetic acid is much lower than due to +I effect of CH3 group in acetic acid is much weaker than in acetic acid and, hence, loses a proton more easily than acetic acid.



(ii) Due to -I-effect of Cl, dispersal of the -ve charge occurs in chloroacetic ion but +I-effect of CH3 group, interpretation of -ve charge occur in acetic ion.

(d) CH3CH2CH=CHCH2CHO

(e) A=CH3COCH3 B=CH3CH2CHO
A gives iodoform test
CH3COCH3+3I2+NaOHCHI3+CH3COONa

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