Haloalkanes and Haloarenes

Topics in this chapter

• Haloalkane Structure and Properties
• Nucleophilic Substitution Mechanisms
• Stereochemistry of Haloalkanes
• Elimination and Addition Reactions
• Haloarene Reactivity and Substitution
• Haloalkane Preparation and Name Reactions
• Free-Radical Halogenation

Cheat sheet

Practice questions

1. Question 1Q-1C250B

   Which of the following alkyl halides undergoes hydrolysis most rapidly via the $S_N1$ mechanism?

   1. A.1-Chlorobutane
   2. B.1-Iodobutane
   3. C.2-Iodobutane
   4. D.2-Iodo-2-methylpropane
   See the answer and solution
2. Question 2Q-8FB659

   Identify the major product formed when 2-bromobutane is treated with alcoholic KOH.

   1. A.Butan-1-ol
   2. B.Butan-2-ol
   3. C.But-1-ene
   4. D.But-2-ene
   See the answer and solution
3. Question 3Q-E9E9E0

   Which of the following compounds is optically active?

   1. A.1-bromobutane
   2. B.2-bromobutane
   3. C.1-bromo-2,2-dimethylpropane
   4. D.1-bromo-2-methylpropane
   See the answer and solution
4. Question 4Q-9BB267

   Chlorobenzene is extremely less reactive towards nucleophilic substitution compared to chloromethane. Which of the following is NOT a valid reason for this?

   1. A.Resonance stabilization of chlorobenzene
   2. B.$sp^2$ hybridized carbon attached to chlorine in chlorobenzene
   3. C.Instability of the phenyl cation formed during $S_N1$ mechanism
   4. D.Repulsion between the approaching nucleophile and the positively charged carbon atom
   See the answer and solution
5. Question 5Q-388641

   What happens when methyl chloride is treated with aqueous KOH?

   1. A.Methane is formed
   2. B.Methanol is formed
   3. C.Dimethyl ether is formed
   4. D.Formaldehyde is formed
   See the answer and solution