(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 tests to distinguish between: (i) Pentan-2-one and Pentan-3-one (ii) Ethanal and Propanal

(a)i) Propanone to Propan-2-ol

OOH
|||
CH3-C-CH3 + Na/alcohol -------> CH3-CH-CH3

ii) Ethanal to 2-Hyroxypropanoic acid
H
|
CH3-C=O + .CN -------> H
|
CH3-C-CN
|
OH
+
H2O -------> |
C
|
OH
CH3-CH-COOH

iii) Toluene to benzoic acid (ref. image )
(b)i) Pentan-2-one and Pentan-3-one
O
||
CH3-C-CH2-CH2-CH3 and O
||
CH3-CH2-C-CH2-CH3
By Iodoform Test
Pentan-2-one being a methyl ketone when treated with NaOl(I2/NaOH)gives yellow precipitate of iodoform but pentan-3-one does not.
O
||
CH3-CH2-CH2-C-CH3 + 3NaOI -----> CH3CH2CH2COONa + CHI3
|
Iodoform (yellow ppt) + 2NaOH
O
||
CH3-CH2-C-CH2-CH3 + NaOI -----> No yellow precipitate of CHI3
ii) Ethanal and Propanal
O
||
CH3-C-H and O
||
CH3-CH2-C-H
By Iodoform test