LN 10 / Haloalkanes and Haloarenes

1. Give reason:
a. C-Cl bond length in chlorobenzene is shorter than C-Cl bond in CH3-Cl
b. 2-bromobutane is optically active but 1-bromobutane is optically inactive.
c. n-butyl bromide has higher boiling point than t-butyl bromide.
d. Racemic mixture is optically inactive.
e. the presence of nitro group o/p position increases the reactivity of haloarenes towards
nucleophilic substitution reaction.
f. Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.
g. Grignard reagent should be prepared under anhydrous conditions.
h. Why is methyl chloride hydrolysed more easily than chlorobenzene.
i. Benzyl chloride is highly reactive towards SN1 reactions, why?
j. Why is cyclohexyl chloride is more reactive than chlorobenzene?
k. Why is chloroform store in dark coloured bottle?
l. Eloctrophilic substitution reactions in haloarenes occur slowly. Why?
m. Haloalkanes, though polar, are insoluble in water. Why?

2. Which one the following more reactive

a. C6H5CH(CH3)Br and C6H5CH(C6H5)Br - SN1
b. CH3CH2CH2CH2CH2-I and CH3CH2CH2CH2CH2-Br - SN2
c. CH3-Br and CH3-I - SN2
d. (CH3)3C-Cl and CH3-Cl - SN2
e. 2-bromo butane and 1-bromo butane - SN2
f.

- SN2
g.

3. Answer the following:

 (CH3)2CHCH(Cl)CH3

4. Write the structure of the following:

a. 1-bromo-4-chlorobut-2-ene g. 4-bromo-3-methyl pent-2-ene

b. 2,4-dinitrochlorobenzene h. 2-(2-chlorophenyl)-1-iodoethane
c. 3-bromo-2-methylprop-1-ene i. 1-Bromo-4-sec-butyl-2-methyl-
d. 1-chloro-4-chlorobenzene benzene
e. 1-chloro-4-ethyl cyclohexane j. 2-chloro-3-methylpentane
f. 3-iodo-4-tert.butyl heptane k. 1,4-dibromobut-2-ene