www.studyadda.

com

Haloalkanes And Haloarenes Previous Years Questions

HALALKANES AND HALOARENES 1

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

1 MARK QUESTIONS 1. Give the IUPAC name of the following compound. [Delhi 2012]
CH 2 C CH 2 Br | CH3

2.

Write the IUPAC name of the following compound (CH3 )3 CCH2 Br . [Delhi 2011]

3.

Write the IUPAC name of the following compound CH2 CHCH2 Br . [All India 2011]

4.

Write the structure of 1, 4-dibromobut-2-ene. [Delhi 2011C]

5.

Write the structure of 2-(2-bromophenyl) butane [Delhi 2011C]

6.

Write the structure of 2-(2- chlorophenyl )-1-isooctane. [All India 2011C]

7.

Write the structure of the following compound: 1-bromo-4-sec. butyl-2-methyl benzene. [All India 2011C]

8.

Which will react faster in S2 N displacement, 1-bromopentane or 2-bromopentane and why? [Foreign 2011, 2010]

9.

Write the IUPAC name of the following. [All India 2010; Delhi 2008]

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

10.

A solution of KOH hydrolysis CH3CHCICH 2CH3 and CH3CH 2CH 2CH 2CI . Which one of these is more easily hydrolyzed? [Delhi 2010]

11.

Give the IUPAC name of the following. [All India 2010; Foreign 2009]

12.

Write the structure of the compound 4- tert.butyl-3-iodoheptane. [All India 2010C]

13.

Write the IUPAC name of the following compound.

[All India 2010C] 14. Write the structure of the compound 1-chloro-4 ethylcyclohexane . [All India 2010C] 15. Draw the structure of the following compound: 4-bromo-3-melhylpent-2-ene. [Foreign 2010] 16. Write the structure of the following organic compound: 2-chloro-3-methylpentane. [All India 2009C] 17. Write a chemical reaction in which the iodide ion replaces the diazonium group in a diazonium salt. [Delhi 2008]

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

18.

Write the IUPAC name of ClCH2C CCH2 Br [All India 2008C]

19.

Write IUPAC name of [Foreign 2008]

20.

Which one of the two compounds CH3 Br and CH 3l will react faster in an SN 2 reaction With OH? [Foreign 2007]

2 MARKS QUESTIONS 21. Explain as to why (i) (ii) alkyl halides, though polar, are Immiscible with water? Grignard's reagent should be prepared under anhydrous conditions? [Foreign 2012] 22. What are ambient nucleophiles? Explain giving an example. [Foreign 2012] 23. Which one in the following pairs of substances undergoes SN 2 substitution reaction faster and why? [Delhi 2009] (i)

(ii)

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

24.

Which one in the following pairs undergoes SN 1 substitution reaction faster and why? [All India 2009] (1)

(2)

25.

Complete the following reaction equations.

(i)

(ii)

CH3CH 2CH CH 2 HBr

[All India 2009] 26. Suggest a possible mechanism for the following reaction :
EtOH , H2O n m BuBr KCN n BuCN

[Delhi 20090; All India 2008C] 27. Suggest a possible reason for the following observations. [Delhi 2009C] (i) (ii) 28. The order of reactivity of haloalkanes is RI > RBr > RCI. Neo- pentyl chloride, (CH3 )3 C CH3CI does not follow SN 2 mechanism.

Complete the following reaction equation. (i)

C6 H5 N2Cl KI

(ii) [Delhi 2008; All India 2008]

5

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

29.

Discuss the mechanism of SN 1 reaction of haloalkanes. [Delhi 2008C]

30.

Give one example of [Delhi 2007] (i) (ii) Wurtz reaction Wurtz fitting reaction

31.

What happens when iodoform is heated silver powder? Write chemical reaction. [All India2007]

32.

What type of reaction is known as nucleophilic substitution reaction? Give one example. [Delhi 2006]

33.

Write IUPAC name of the following compound. [All India 2008] (i)

(ii)

3 MARKS QUESTIONS 34. 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] 35. Answer the following questions. (i) What is meant by chirality of a compound? Give an example.

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

(ii)

Which one of the following compound is more easily hydrolyzed by KOH and why?
CH3CHCICH 2CH3 or CH3CH 2CH 2CH 2CI

(iii)

Which one undergoes SN 2 substitution reaction faster and why?

l

or

Cl

[All India 2012] 36. Answer the following. (i) (ii) (iii) Haloalkanes easily dissolve is organic solvents Why? What is known as racemic mixture? Give an example. Of the two bromo derivatives
C6 H5CH (CH3 ) Br and (C6 H5 )CH (C6 H5 ) Br which one is more reactive in SN 1 substitution

reaction and why? [Delhi 2011] 37. Rearrange the compounds of each of the following sets in order of reactivity towards SN 2 displacement. (i) (ii) (iii) 2-bromo-2-methyl butane, 1-bromopentane, 2- bromopentane. 1-bromo-3-methyl butane, 2-bromo-2-methyl butane, 3-bromo-2-methyl butane. 1-bromobutane, 1-bromo-2, 2-dimethyl propane, 1-bromo-2-methyl butane 1-bromo-3methyl butane [All India 2011] 38. (i) Write the mechanism of the following reaction.
EtOH , H O n BuCN n - n BuBr KCN
2

(ii)

Why is the dipole moment of chlorobenzene lower than that cyclohexyl chloride? [Delhi 2011C]

39.

(i)

Write a chemical test to distinguish between

7

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

(a) (b) (ii)

chlorobenzene and benzyl chloride chloroform and carbon tetrachloride Why is methyl chloride hydrolysed more easily than chlorobenzene? [All India 2011C]

40.

Complete die following reaction equations.

(i)

(ii)

(iii)

CH3CH 2CH CH2 +HBr

[Foreign 2011, 2009] 41. (i) (ii) (a) (b) State one use of DDT and iodoform. Which compound in the following? Couples will react faster in SN 2 displacement and why? 1-bromopentane or 2-bromopentane 1 bromo-2-methylbutane or 2 bromo-2- methyl butane. [Delhi 2010] 42. How would you differentiate between SN 1 and SN 2 mechanism of substitution reactions? Give one example of each. [All India 2010] 43. Explain why (i) the dipole moment of chlorobenzene is lower than that of cydohexyl chloride?
8

www.studyadda.com

Haloalkanes And Haloarenes Previous Years Questions

(ii) (iii)

alkyl halides though polar are immiscible with water. in the pair, (CH 3 )3 C Cl and CH 2 Cl , CH 2 Cl will react faster in SN 2 reaction with OH. [All India 2010C]

44.

Give reasons for the following observations. (i) (ii) (iii) p-dichlorobenzene has higher melting point than those of o and m-isomers. Haloarenes are less reactive than haloarenes towards nucleophilic substitution reaction. The treatment of alkyl chloride with aqueous KOH leads to the formation of alcohol but in the presence of alcoholic = KOH, alkenes is the major product. [All India 2009C Delhi 2008, 2008C]