Q. 27

(a) An organic co

Answer :

(a) The compound with molecular formula C7H6O forms a 2,4-DNP derivative and reduces Tollen's reagent, so it is an aldehyde. It undergoes Cannizzaro reaction, so the aldehyde group will be directly attached to the benzene ring. On oxidation it gives benzoic acid. So, the compound will be benzaldehyde. The reactions are as follows-


2.4dnp.png


C6H5CHO + 2[Ag(NH3)2]+ + 3OH- C6H5COO- + 2Ag + 4NH3 + 2H2O


(Benzaldehyde)


2C6H5CHO conc. NaOH C6H5COONa + C6H5CH2OH


(Benzaldehyde) (sodium benzoate) (benzyl alcohol)


C6H5CHO (O) C6H5COOH


(Benzoic acid)


(b) (i) C6H5OH + FeCl3 C6H5O-FeCl2


(Phenol) (Violet color complex)


CH3CH2CH2OH + FeCl3 no reaction


(propanol)


(ii) C6H5COOH + NaHCO3 C6H5COONa + CO2 + H2O


(benzoic acid) (brisk effervesence)


C6H6 + NaHCO3 no reaction


(benzene)


OR


(a) A = CH3COOH (oxidation) acetic acid


B = CH3COCl acetyl chloride


C= CH3CONH2 acetamide


D = CH3CONHBr N- bromoacetamide


(b) Presence of EWG increases the acidity of carboxylic acid by stabilizing the negative charge of conjugate base by –I effect.


Moreover, -I effect of F is greater than that of Cl.


More the no. of EWG, more will be the acidity.


From above points, the increasing order of acidity will be


HCOOH< ClCH2COOH<CCl3COOH< CF3COOH


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