Problem 1
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary). vinyl or aryl halides: (i) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}(\mathrm{Cl}) \mathrm{CH}_{3}\) (ii) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{Cl}\) (iii) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{2} \mathrm{I}\) (iv) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{CH}(\mathrm{Br}) \mathrm{C}_{6} \mathrm{H}_{5}\) (v) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}\) (vi) \(\mathrm{CH}_{3} \mathrm{C}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{CH}_{2} \mathrm{Br}\) (vii) \(\mathrm{CH}_{3} \mathrm{C}(\mathrm{Cl})\left(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\right.\) (viii) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}(\mathrm{Cl}) \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (ix) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHC}(\mathrm{Br})\left(\mathrm{CH}_{3}\right)_{2}\) (x) \(p-\mathrm{ClC}_{6} \mathrm{H}_{4} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (xi) \(\mathrm{m}-\mathrm{Cl} \mathrm{CH}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) (xii) \(\mathrm{o}-\mathrm{Br}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}\)
Problem 2
Give the IUPAC names of the following compounds: (i) \(\mathrm{CH}_{3} \mathrm{CH}(\mathrm{Cl}) \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}\) (ii) \(\mathrm{CHF}_{2} \mathrm{CBrClF}\) (iii) \(\mathrm{ClCH}_{2} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{Br}\) (iv) \(\left(\mathrm{CCl}_{3}\right)_{3} \mathrm{CCl}\) (v) \(\mathrm{CH}_{3} \mathrm{C}\left(p-\mathrm{ClC}_{6} \mathrm{H}_{4}\right)_{2} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}\) (vi) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}=\mathrm{CClC}_{6} \mathrm{H}_{4} \mathrm{I}-p\)
Problem 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 0
Problem 4
Which one of the following has the highest dipole moment? (i) \(\mathrm{CH}_{2} \mathrm{Cl}_{2}\) (ii) \(\mathrm{CHCl}_{3}\) (iii) \(\mathrm{CCl}_{4}\)
Problem 5
A hydrocarbon \(\mathrm{C}_{5} \mathrm{H}_{10}\) does not react with chlorine in dark but gives a single monochloro compound \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Cl}\) in bright sunlight. Identify the hydrocarbon.
Problem 6
Write the isomers of the compound having formula \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}\).
Problem 8
What are ambident nucleophiles? Explain with an example.
Problem 9
Which compound in each of the following pairs will react faster in \(\mathrm{S}_{\mathrm{N}} 2\) reaction with - OH? (i) \(\mathrm{CH}_{3} \mathrm{Br}\) or \(\mathrm{CH}_{3} \mathrm{I}\) (ii) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCl}\) or \(\mathrm{CH}_{3} \mathrm{Cl}\)
Problem 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.
Problem 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
