Show the transition state of each step of the following alkene addition reaction. Be sure to indicate whether the transition state in each is reactant-like or product-like.

Using the bond-dissociation energies in Table 5.6 (see Section 5.3.1), estimate the equilibrium constant of the following reaction at 298 K.

Draw all resonance structures of the following carbanion and carbocation.

(a)

(b)

Identify the following halogen-containing compounds as a haloalkane, haloalkene, or haloarene.

(b)

Identify the following halogen-containing compounds as a haloalkane, haloalkene, or haloarene.

(c)

Identify the following halogen-containing compounds as a haloalkane, haloalkene, or haloarene.

(d)

Identify the following halogen-containing compounds as a haloalkane, haloalkene, or haloarene.

(e)

Identify the following halogen-containing compounds as a haloalkane, haloalkene, or haloarene.

(f)

Suppose you intend to synthesize the secondary alkyl halide from each reaction shown.

(a) What is the atom economy of each reaction?

(c) Which reaction would you consider greener? Why?

From the IUPAC name, draw the corresponding structure.

(a) (R)-6-iodo-3-isopropylnon-1-ene

From the IUPAC name, draw the corresponding structure.

(b) (1R,2S)-1-chloro-2-methylcyclobutane

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(a)

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(b)

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(d)

Predict the product of the following haloalkane syntheses.

(a)

Predict the product of the following haloalkane syntheses.

(c) HBr↗HOOH

Predict the product of the following haloalkane syntheses.

(e)

Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.