Q10.1 Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
Solution

Q10.2 Give the IUPAC names of the following compounds:
Solution

Q10.3 Write the structures of the following organic halogen compounds.
(i) 2-Chloro-3-methylpentane
(ii) p-Bromochlorobenzene
(iii) 1-Chloro-4-ethylcyclohexane
(iv) 2-(2-Chlorophenyl)-1-iodooctane
(v) 2-Bromobutane
(vi) 4-tert-Butyl-3-iodoheptane
(vii) 1-Bromo-4-sec-butyl-2-methylbenzene
(viii) 1,4-Dibromobut-2-ene
Solution

Q10.4 Which one of the following has the highest dipole moment?
(i) CH₂Cl₂
(ii) CHCl₃
(iii) CCl₄ Solution

Q10.5 A hydrocarbon C₅H₁₀ does not react with chlorine in dark but gives a single monochloro compound C₅H₉Cl in bright sunlight. Identify the hydrocarbon Solution

Q10.6 Write the isomers of the compound having formula C₄H₉Br Solution

Q10.7 Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol (ii) 1-chlorobutane (iii) but-1-ene. Solution

Q10.8 What are ambident nucleophiles? Explain with an example. Solution

Q10.9 Which compound in each of the following pairs will react faster in S_N 2 reaction with –OH?
(i) CH₃Br or CH₃ I
(ii) (CH₃ ) ₃CCl or CH₃Cl
Solution

Q10.10 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.
Solution

Q10.11 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.
Solution

Q10.12 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?
Solution

Q10.13 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform Solution

Q10.14 Write the structure of the major organic product in each of the following reactions:
Solution

Q10.15 Write the mechanism of the following reaction:
Solution

Q10.16 Arrange the compounds of each set in order of reactivity towards S_N2 displacement:
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.
Solution