Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide.

(a) CH₃CHCFCH₃

(b) (CH₃)₃CBr

(c) CH₃CCl₃

Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide.

Give the structures of the following compounds.

a. methylene iodide

b. carbon tetrabromide

Give the structures of the following compounds.

e. 2-bromo-3-ethyl-2-methylhexane

f. isobutyl bromide

Give the structures of the following compounds.

g. cis-1-fluoro-3-(fluoromethyl)cyclohexane

h. tert-butyl chloride

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

(a) (CH₃)₂CHCH₂Cl

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

b. (CH₃)₃CBr

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

c.

d.

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

e.

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

(f)

Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

a. ethyl chloride or ethyl iodide

b. 1-bromopropane or cyclopropane

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene

d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane

a. Propose a mechanism for the following reaction:

b. Use the bond-dissociation enthalpies given in Table 4-2 (page 167) to calculate the value of ΔH° for each step shown in your mechanism. (The BDE for CH₂=CHCH₂―Br is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ΔH° for the reaction. Are these values consistent with a rapid free-radical chain reaction?

Under appropriate conditions, (S)-1-bromo-1-fluoroethane reacts with sodium methoxide to give pure (S)-1-fluoro-1-methoxyethane.

a. Why is bromide rather than fluoride replaced?

b. Draw perspective structures (as shown on the previous page for 2-bromobutane) for the starting material, the transition state, and the product.

c. Does the product show retention or inversion of configuration? d. Is this result consistent with reaction by the SN2 mechanism?

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

a. isopropyl bromide and n-butyl bromide

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

a. butan-1-ol

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

b. isopropyl chloride and tert-butyl bromide

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

b. 1-fluorobutane

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

c. 1-bromobutane and 1-chlorobutane

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

a. Give a mechanism for this reaction, showing how the two products arise as a ­consequence of the resonance-stabilized intermediate.

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

b. The bromination of cyclohexene using NBS gives only one major product, as shown on the previous page. Explain why there is no second product from an allylic shift.

Show how free-radical halogenation might be used to synthesize the following ­compounds. In each case, explain why we expect to get a single major product.

(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)

(b) 2-bromo-2-methylbutane

Show how free-radical halogenation might be used to synthesize the following ­compounds. In each case, explain why we expect to get a single major product.

(c)

Show how free-radical halogenation might be used to synthesize the following ­compounds. In each case, explain why we expect to get a single major product.

(d)

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

a.

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

b.

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

c.