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TEST I

HALO ALKANES
DATE : 02.06.2014 TIME : 1hr


1.Find out and give the reason for which one of the following has the highest
dipole moment? 2M
(i) CH2Cl2 (ii) CHCl3 (iii) CCl4
Answer: CHCl3 has the highest dipole amongst the given molecules. In both CH2Cl2 and
CCl4 the net dipole is zero because the resultant dipole in both the molecules is equal
and opposite , which cancel each other making the net dipole as zero.
2. Write the equations for the preparation of 1-iodobutane from
6M
(i) 1-butanol (ii) 1-chlorobutane (iii) but-1-ene. And specifiy which named
reaction they follow.
Answer: (i) 1-butanol :RI may be obtained by heating alcohols with sodium or
potassium iodide in 95% phosphoric acid.
(ii) 1-chlorobutane: Alkyl iodides are often prepared by the reaction of alkyl
chlorides/bromides with NaI in dry acetone. This reaction is known as Finkelstein
reaction.

(iii) but-1-ene.: An alkene is converted to corresponding alkyl halide by reaction with
hydrogen chloride,hydrogen bromide or hydrogen iodide.markonokovs

3. Answer the following: 5M

a.What are ambident nucleophiles? Explain with an example.

b. Which compound in each of the following pairs will react faster in SN2 reaction
with OH?
(i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl

Answer:
a.The nucleophiles which can attack through different sites are called ambident
nucleophiles. Eg CN, NO2

b. (i)The C-I bond dissociation energy is 234KJ/mol and the C-Br bond dissociation
energy is 293KJ/mol.Therefore CH3I reacts faster than CH3Br with OH ions as Iodide is
a better leaving group.

(ii)In SN2 reaction the nucleophile attacks from the back side of the alpha
carbon.Presence of bulky groups on or near the alpha carbon hinders the approach of
the nucleophile to the alpha carbon.The reaction becomes difficult due to steric
hinderance. Primary alkyl halide reacts the fastest and tertiary the slowest. Therefore
CH3Cl will react faster in SN2 reaction with OH-.
4. Write few differences between sn1 and sn2 reactions each with an example
5M

5. How the following conversions can be carried out?
5M
A. Benzene to diphenyl
Fittig reaction:



B. Ethyl bromide to Ethyl magnesium bromide


c. A mixture of an alkyl halide and aryl halide to Alkylarene

Wurtz-Fittig reaction:


6.Write the IUPAC names of the following compounds:
2M
a.
----- 3-Bromopropene

b. --------- Chlorophenylmethane

c. (CH3)3CCH2Br1-Bromo-2,2-dimethylpropane


d. ..4 chloro benzene sulphonicacid