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Question

(a) How will you convert the following :
(i) Propanone to Propan-2-ol
(ii) Ethanal to 2-hydroxy propanoic acid
(iii) Toluene to benzoic acid
(b) Give simple chemical test to distinguish between :
(i) Pentan-2-one and Pentan-3-one
(ii) Ethanal and Propanal

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Solution

(a) (i) CH3O||CPropaneCH3+H2Ni, Pt or Pd−−−−−−CH3OH|CPropan-2-olCH3

(ii) CH3CHOEthanalHCN−−CH3H|C|OHCNH+/H2O−−−−CH3OH|CH2Hydroxypropanoic acidCOOH

(b) Chemical tests to distinguish between :
(i) Pentan - 2 - one and Pentan-3-one : On treating with NaOI(I2/NaOH) pentan - 2 - one gives yellow ppt. of iodoform but pentan-3-one does not.
CH3CH2CH2Pentan3oneO||CCH3+3NaOICH3CH2CH2COONa+CHI3Iodoform(Yellowppt.)+2NaOHCH3CH2O||CCH2CH3NaOI−−No yellow ppt. iodoform

(ii) Ethanal and Propanal : Ethanal when trated with I2/NaOH(or NaOI) given yellow ppt. of iodoform but propanal does not.
CH3CHOEthanal+3NaOICHI3Yellowppt.+HCOONa+2NaOH
CH3CH2CHOPropanalI2NaOH−−− No yellow ppt. of iodoform

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