Question 1
Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcyclohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene

Question 2
Why is sulphuric acid not used during the reaction of alcohols with KI?

Question 7
Which alkyl halide from the following pairs would you expect to react more rapidly by an S_N2 mechanism? Explain your answer.

Question 8
In the following pairs of halogen compounds, which compound undergoes faster S_N1 reaction?

Question 1
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(i) (CH₃)₂CHCH(Cl)CH₃
(ii) CH₃CH₂CH(CH₃)CH(C₂H₅)Cl
(iii) CH₃CH₂C(CH₃)₂CH₂I
(iv) (CH₃)₃CCH₂CH(Br)C₆H₅
(v) CH₃CH(CH₃)CH(Br)CH₃
(vi) CH₃C(C₂H₅)₂CH₂Br
(vii) CH₃C(Cl)(C₂H₅)CH₂CH₃
(viii) CH₃CH=C(Cl)CH₂CH(CH₃)₂
(ix) CH₃CH=CHC(Br)(CH₃)₂
(x) p-ClC₆H₄CH₂CH(CH₃)₂
(xi) m-ClCH₂C₆H₄CH₂C(CH₃)₃
(xii) o-Br-C₆H₄CH(CH₃)CH₂CH₃

Question 2
Give the IUPAC names of the following compounds:
(i) CH₃CH(Cl)CH(Br)CH₃
(ii) CHF₂CBrClF
(iii) ClCH₂C≡CCH₂Br
(iv) (CCl₃)₃CCl
(v) CH₃C(p-ClC₆H₄)₂CH(Br)CH₃
(vi) (CH₃)₃CCH=CClC₆H₄I-p

Question 4
Which one of the following has the highest dipole moment?
(i) CH₂Cl₂
(ii) CHCl₃
(iii) CCl₄

Question 7
Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol
(ii) 1-chlorobutane
(iii) but-1-ene

Question 8
What are ambident nucleophiles? Explain with an example.

Question 10
Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:
(i) 1-Bromo-1-methylcyclohexane
(ii) 2-Chloro-2-methylbutane
(iii) 2,2,3-Trimethyl-3-bromopentane.

Question 11
How will you bring about the following conversions?
(i) Ethanol to but-1-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-1-ene to but-2-ene
(ix) 1-Chlorobutane to n-octane
(x) Benzene to biphenyl.

Question 12
Explain why
(i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
(ii) alkyl halides, though polar, are immiscible with water?
(iii) Grignard reagents should be prepared under anhydrous conditions?

Question 14
Write the structure of the major organic product in each of the following reactions:

Question 15
Write the mechanism of the following reaction:

Question 16
Arrange the compounds of each set in order of reactivity towards SN2 displacement:
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2- methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.

Question 17
Out of C₆H₅CH₂Cl and C₆H₅CHClC₆H₅, which is more easily hydrolysed by aqueous KOH?

Question 19
How the following conversions can be carried out?
(i) Propene to propan-1-ol
(ii) Ethanol to but-1-yne
(iii) 1-Bromopropane to 2-bromopropane
(iv) Toluene to benzyl alcohol
(v) Benzene to 4-bromonitrobenzene
(vi) Benzyl alcohol to 2-phenylethanoic acid
(vii) Ethanol to propanenitrile
(viii) Aniline to chlorobenzene
(ix) 2-Chlorobutane to 3, 4-dimethylhexane
(x) 2-Methyl-1-propene to 2-chloro-2-methylpropane
(xi) Ethyl chloride to propanoic acid
(xii) But-1-ene to n-butyliodide
(xiii) 2-Chloropropane to 1-propanol
(xiv) Isopropyl alcohol to iodoform
(xv) Chlorobenzene to p-nitrophenol
(xvi) 2-Bromopropane to 1-bromopropane
(xvii) Chloroethane to butane
(xviii) Benzene to diphenyl
(xix) tert-Butyl bromide to isobutyl bromide
(xx) Aniline to phenylisocyanide