1.A solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl.

Which one of these

is more easily hydrolysed?

2. : Draw the structure of major monohalogen product formed in the following reaction

3. Predict the order of reactivity of four isomeric bromobutanes in S N1 reaction.

4. Predict the order of reactivity of the following compounds in S N1 reaction :

C6H5CH2Br, C6H5C(CH3) (C6H5)Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br

5. Arrange the following in increasing order of boiling point:

(i) CH3CH2CH2CH2Br
(ii) (CH3)3.Br
(iii) (CH3)2C.Br

6. Complete the following reaction equations :

7. How are the following conversions carried out?

(i) Benzyl chloride to benzyl alcohol,
(ii) Methyl magnesium bromide to 2-methyl- propan-2-ol.

8. Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction.

Give two reasons for the same.

9. Account for the following:

(i) The C – Cl bond length in chlorobenzene is shorter than that in CH3 – Cl.
(ii) Chloroform is stored in closed dark brown bottles

10. Explain why :

(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(b) Alkyl halides, though polar, are immiscible with water.

11. Although chlorine is an electron withdrawing group, yet it is ortho-, para-directing in

electrophilic aromatic substitution reactions. Explain why it is so?

12. (a) Write the structural formula of A, B, C and D in the following sequence of reaction:

(b) Illustrate Sandmeyer’s reaction with the help of a suitable example.

13. Give the IUPAC name of the following compounds(a) (CH3)3 CCH2Br (b)CH2 = CHCH2Br
(c)