PREVIOUS YEARS

EXAMINATION QUESTIONS
TOPIC 2

@1Mark Questions
Why is t-butyl bromide more reactive towards SN1 reaction as compared to
n-butyl bromide? All india 2019
2. Predict the major product formed whensodium ethoxide reacts with tert.butyl

chloride. CBSE 2016 C

3. Out of chlorobenzene and benzyl chloride wich one gets easily hydrolysed by
aqueous NaOH and why? CBSE 2018

4. Write the structure of an isomer of cmpound C4H9Br which is most reactive

towards SN1 reaction. All India 2016
5. Out of them which is more reactive towards SN1 reaction and why? Delhi 2016

6. Which would undergo SN1 reaction faster in the following pair?

7. Which would undergo SN 2 reaction faster in the following pair and why? |

8. Which would undergo S N 2 reaction faster in the following pair and why? Foreign
2015
9. Identify the chiral molecule in the following pair.

All india 2014, Delhi 2014

10. What happens when CH —Br is treated with KCN? Delhi 2013

11. What happens when ethy! chloride is treated with aqueous KOH? Delhi 2013

12. Which compound in the following pair undergoes faster towards SN 1 reaction?

13. Give reasons for the following :

(a) The presence of —-NO2 group at ortho or para position increases the
reactivity of haloarenes towards, nucleophilic substitution reactions.
(b) p-dichlorobenzene has higher melting point than that of ortho or
meta isomer.
(©) Thionyl chloride method is preferred for preparing alkyl chloride from

alcohols. All india 2019

14. Out of (CH3 )C—Br and (CH3)C—l, which one is more reactive towards
SN1 and why?
(i) Write the product formed when P-nitrochlorobenzene is heated with aqueous NaOH at
443 K followed by acidification.

(ii) Why dextro and laevo-rotatory isomers of butan-2-ol are difficult to separate by
fractional distillation? Delhi 2019
15. Identify the chiral molecule in the following pair:

(ii) Write the structure of the product when chlorobenzene is treated with
methyl chloride in the presence of sodium metal and dry ether.
(ii) Write the structure of the alkene formed by dehydrohalogenation of 1-bromo 1-
methylcyclohexane with alcoholic KOH. cbse 2018

16. Write the product(s) formed when (i) 2-bromopropane undergoes dehydrohalogenation
reaction.
(ii) Chlorobenzene undergoes nitration reaction
(iii) Methylbromide is treated with KCN.

CBSE 2018 C
17. Following compounds are given to you:
-bromopentane,
2-hromo-2-methylbutane,
1-bromopentane

(i) Write the compound which is most reactive towards SN 2 reaction.

(ii) rite the compound which is optically active.
(iii) Write the compound which is most reactive towards B-elimination reaction.
Delhi 2017; All india 2017

18. How do you convert the following?

(i) Chlorobenzene to biphenyl.
(ii) Propene to 1-iodopropane.
(iii) 2-bromobutane to but-2-ene. Dethi2015

19.

20. Give reasons.

(i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—ClL

(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride
(iii) Sy1 reactions are accompanied by racemisation in optically active alkyl
Halides Foreign 2015
21. How can the following conversions be carried out?

(i) Aniline to bromobenzene

(ii) Chlorobenzene to 2-chloroacetophenone
(iii) Chloroethane to butane All india 2015¢

22. Delhi 2014C

23.

24.
25. Although, chlorine is an electron withdrawing group, yet it is ortho, para-directing in
electrophilic aromatic substitution reactions. Explain, why is it so? Delhi 2012
26. Answer the following questions:
(i) What is meant by chirality of a compound? Give an example,

(ii) Which one of the following compounds is more easily hydrolysed

by KOH and why?
CH3CHCICH2CH3
or CH3CH2CH2CH2CI
(iii) Which one undergoes SN2 substitution reaction faster and why?