1. Why is an alkane more chemically reactive than the corresponding alkane?

2. Draw and name all products of the following reactions.

   1. • (a) CH₃–CH=CH–CH₃ + Cl₂ →

      • (b) 3-methyl-3-hexene + water →

      • (c) benzene + bromine (catalyzed by FeBr₂) →

      • (d) 2-bromopentane + sodium hydroxide →

      • (e) CH₃CH₂OH + CH₃CH₂COOH →

      • (f) CH₃–CH=CH₂ + H₂ →

      • (g) N-ethylpentanamide + water (catalyzed by H₂SO₄) →

3. Classify each type of reaction in the previous question.

4. Draw and name the organic products of the following reactions.

   1. • (a) oxidation of hexan-3-ol

      • (b) reduction of methanal

      • (c) oxidation of 3-methylpentanal

      • (d) reduction of 2,2-dimethylheptan-3-one

      • (e) oxidation of 3-ethyl-2-methylhexan-1-ol

      • (f) reduction of 3-methylhept-2-ene (Hint: reduction can be thought of as the addition of H₂, see p.106 #9)

Classify each of the following reactions and draw a condensed structural diagram of the product(s).

• 1. CH₂=CHCH₃ + H₂O →

  2. CH₃CH₂OH (rxn catalyzed by H₂SO₄) →

  3. CH₃CH₂CH₂OH + CH₃COOH →

  4. CH₃CHO + [H] →

  5. CH₃CH₂CH₂COOCH₃ + H₂O →

  6. CH₃CH(CH₃)OH + [O] →

  7. CH₃(CH₂)₅CH₂OH + CH₃CH₂CH₂OH →

Write structural diagrams for each of the following reactions.

• • (1) ethan-1-ol + [O] →

  • (2) 2-methylpentan-2-ol + [O] →

  • (3) butan-2-ol + [O] →

  • (4) butanal + [O] →

  • (5) butanal + [H] →

  • (6) 2-hexanone + [O] →

  • (7) pentan-1-ol + [H] →

  • (8) propanoic acid + [H] →

Classify each of the following reactions and predict the possible products for the initial reaction.