GRADE XII (CHEMISTRY)

HALOALKANES AND HALOARENES

MOST IMPORTANT QUESTIONS

IUPAC NOMENCLATURE
1. Give the IUPAC name of the following compound : (All India 2010)

2. Write the IUPAC name of the following compound : (CH 3)3 CCH2Br (Delhi 2010)
3. Write the IUPAC name of the following compound : (All India 2010)

4. Give the IUPAC name of the following compound. (Delhi 2012)

5. Write the IUPAC name of (CH3)2CH.CH(Cl)CH3. (Delhi 2013)

6. Out of

which is an example of allylic halide? (All India 2017)

7. Out of

which is an example of vinylic halide? (All India 2017)

8. Out of

which is an example of a
benzylic halide? (All India 2017)
 9. Write the structures of the following organic halogen compounds :
(i) 4-tert-Butyl-3-iodoheptane
(ii) 4-Bromo-3-methylpent-2-ene (Comptt. All India 2014)
10. Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcydohexane
(iii) 4-tert. Butyl-3-iodoheptane

PHYSICAL PROPERTIES
1. Arrange the following in increasing order of boiling point:
(i) CH3CH2CH2CH2Br
(ii) (CH3)3.CBr
(iii) (CH3)2CH.Br (Comptt. All India 2012)
2. (a) Why does p-dichlorobenzene have a higher m.p. than its o- and m-isomers?
(b) Why is (±)-Butan-2-ol optically inactive? (Delhi 2013)
3. Explain why :
(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(b) Alkyl halides, though polar, are immiscible with water. (Comptt. All India 2013)
4. Arrange the following compounds in increasing order of reactivity towards S N2
displacement:
2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentane (Comptt. All India
2017)
5. Arrange each set of compounds in order of increasing boiling points :
(i) Bromomethane, bromoform, chloromethane, dibromomethane
(ii) 1- Chloropropane, isopropylchloride, 1- chlorobutane.
6. Which one of the following has the highest dipole moment?
(i)CH3CI2 (ii) CHCl3 (iii) CCI4
7. p-dichlorobenzene has higher m.p. and lesser solubility than those of o-and m-
isomers. Discuss. (C.B.S.E. Delhi 2013)

CHEMICAL PROPERTIES
1. Draw the structure of major monohalogen product formed in the following reaction :
(Comptt. Delhi 2012)

2. Draw the structure of major monohalogen product in the following reaction : (Comptt.
Delhi 2012)

3. What happens when CH3 — Br is treated with KCN? (Delhi 2013)

4. What happens when ethyl chloride is treated with aqueous KOH? (Delhi 2013)
5. A hydrocarbon C5H12 gives only one mono-chlorination product. Identify the
hydrocarbon. (Comptt. Delhi 2013)
6. Complete the following reaction equations : (All India 2009)

7. Haloalkanes undergo nucleophilic substitution whereas haloarenes undergo

electrophilic substitution. Explain. (Comptt. Delhi 2012)
8. Chlorobenzene is extremely less reactive towards a nucleophilic substitution
reaction. Give two reasons for the same. (Delhi 2013)
9. Account for the following:
(i) The C – Cl bond length in chlorobenzene is shorter than that in CH 3 – Cl.
(ii) Chloroform is stored in closed dark brown bottles. (Delhi 2013)
10. Write the equations for the preparation of 1-bromobutane from :
(i) 1-butanol (ii) but-l-ene (Comptt. All India 2016)
11. Draw the structure of major monohalo product in each of the following reactions :
(Delhi 2014)

12. What are ambident nucleophiles? Explain with an example. (Comptt. All India 2014)
13. How will you carry out the following conversions :
(i) 2-Bromopropane to 1-bromopropane
(ii) Benzene to p-chloronitrobenzene
14. Answer the following :
(i) Haloalkanes easily dissolve in organic solvents, why?
(ii) What is known as a racemic mixture? Give an example.
15. Although chlorine is an electron withdrawing group, yet it is ortho-, para-directing in
electrophilic aromatic substitution reactions. Explain why it is so? (Delhi 2012)
16. Account for the following :
(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(b) Alkyl halides, though polar, are immiscible with water.
(c) Grignard’s reagents should be prepared under anhydrous conditions. (Comptt. All
India 2012)
17. Give reasons for the following :
(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.
(ii) (±) 2-Butanol is optically inactive.
(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.
(All India 2013)
18. Give reasons :
(a) n-Butyl bromide has higher boiling point than t-butyl bromide.
(b) Racemic mixture is optically inactive.
(c) The presence of nitro group (-NO2) at o/p positions increases the reactivity of
haloarenes towards nucleophilic substitution reactions. (Delhi 2015)
19. How can the following conversions be carried out :
(i) Aniline to bromobenzene
(ii) Chlorobenzene to 2-chloroacetophenone
(iii) Chloroethane to butane (All India 2015)
20. What happens when
(i) Chlorobenzene is treated with Cl 2/FeCl3,
(ii) Ethyl chloride is treated with AgNO2,
(iii) 2-bromopentane is treated with alcoholic KOH?
Write the chemical equations in support of your answer. (All India 2015)
21. How do you convert: (All India 2016)
(i) Chlorobenzene to biphenyl
(ii) Propene to 1-iodopropane
(iii) 2-bromobutane to but-2-ene
22. Write the major product(s) in the following: (All India 2016)

23. What happens when

(i) CH3—Cl is treated with aqueous KOH?
(ii) CH3—Cl is treated with KCN?
(iii) CH3—Br is treated with Mg in the presence of dry ether? (Comptt. All India 2016)
24. Write the structural formula of A, B, C and D in the following sequence of reaction:

25. Electrophilic substitution reactions in haloarenes occur slowly. Why?

26. Why is sulphuric acid not used during the reaction of alcohols with KI?
27. Draw the structures of major monohalo products in each of the following reactions:
 28. Identify A, B, C, D, E, R and R1 in the following:

29. How will you bring about the following conversions?

(I) Ethanol to but-l-yne.
(ii) Ethane to bromoethene
(iii) Propene to 1-nitropropane
(iv) Toluene to benzyl alcohol
(v) Propene to propyne
(vi) Ethanol to ethyl fluoride
(vii) Bromomethane to propanone
(viii) But-l-ene to but-2-ene
(ix) 1-Chlorobutane to n-octane
(x) Benzene to biphenyl

30. Write the structure of the major organic product in each of the following reactions:

31. Write the mechanism of the following reaction:

SN1 AND SN2 MECHANISM

1. A solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl. Which one of
these is more easily hydrolysed? (Delhi 2010)
2. In the following pair of compounds, which will react faster by SN1 mechanism and
why? (Comptt. Delhi 2012)

3. Predict the order of reactivity of the following compounds in SN1 reaction :

C6H5CH2Br, C6H5C(CH3) (C6H5)Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br (Comptt. Delhi
2012)
4. Which would undergo SN2 reaction faster in the following pair and why? (Delhi 2015)

5. Which would undergo SN1 reaction faster in the following pair : (All India 2015)

6. Out of

which is more reactive towards SN1 reaction and why? (Delhi 2016)
7. Write the structure of an isomer of compound C4H9Br which is most reactive towards
SN1 reaction. (All India 2016)
8. Which one in the following pairs of substances undergoes S N2 substitution reaction
faster and why? (Delhi 2009)

9. Which one in the following pairs undergoes SN1 substitution reaction faster and why?
(All India 2009)

10. Out of SN1 and SN2, which reaction occurs with

(a) Inversion of configuration
(b) Racemisation (Delhi 2014)
11. Which compound in each of the following pairs will react faster in S N2 reaction with —
OH?
(i) CH3Br or CH3I (ii) (CH3)3 CCl or CH3Cl (Comptt. All India 2016)
12. Which alkyl halide from the following pair is (i) Chiral and (ii) undergoes S N1 reaction
faster?
 (a) (CH3)2CBr
(b) CH3CH2CHBrCH3 (Comptt. Delhi 2017)
13. Of the two bromoderivatives, C6H5CH (CH3)Br and C6H5CH(C6H5)Br, which one is
more reactive in SN1 substitution reaction and why? (Delhi 2011)
14. Rearrange the compounds of each of the following sets in order of reactivity towards
SN2 displacement :
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) l-Bromo-3-methylbutane, 2-Bromo-2-methyl-butane, 3-Bromo-2-methylbutane
(iii) 1-Bromobutane, l-Bromo-2,2-dimethyl-propane, l-Bromo-2-methylbutane (All
India 2011)
15. Which one undergoes SN2 substitution reaction faster and why?

16. SN1 reactions are accompanied by racemization in optically active alkyl halides.
Why?
17. In the following pairs of the halogen compounds which compound undergoes faster
SN1 reaction. (Comptt. Delhi 2016)

18. Following compounds are given to you:

2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane
(i) Write the compound which is most reactive towards SN2 reaction.
(ii) Write the compound which is optically active.
(iii) Write the compound which is most reactive towards β – elimination reaction.
(Delhi 2017)

DISTINGUISH TEST
1. Give a chemical test to distinguish between C 2H5Br and C6H5Br. (Comptt. All India
2012)