14
Write the structure of the major organic product in each of the following reactions:
(i) CH3CH2CH2Cl + NaI  
(ii) (CH3)3CBr  +  KOH  
(iii) CH3CH(Br)CH2CH3  +  NaOH  
(iv) CH3CH2Br  +  KCN  
(v) C6H5ONa  +  C2H5Cl  
(vi) CH3CH2CH2OH  + SOCl2  
(vii) CH3CH2CH = CH2 +  HBr  
(viii) CH3CH = C(CH3)2  +  HBr   
6 15
Write the mechanism of the following reaction:
nBuBr  +  KCN  
  nBuCN
6 16
Arrange the compounds of each set in order of reactivity towards SN2
displacement:
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane,
1-Bromo-3-methylbutane 6