(i) Using bond dissociation energies, calculate ∆H° for the following reactions. [BDE for O―H = 110 kcal /mol.]

(b)

(a) Rank the following carbocations from least stable to most stable. (b) Which would you expect to form first? (c) Which would you expect to react most quickly with a bromide ion (Br^⁻) ? [Carbocations, like radicals, are electron deficient.]

Given that A is more stable than B, draw a reaction coordinate diagram that rationalizes the fact that A forms more quickly than B in the following reaction.

Rationalize the fact that reaction A results in an unequal mixture of products, but reaction B yields an equal mixture of two products.

Predict the product that results from the following 'pushed electrons.'

(a)

Predict the product that results from the following 'pushed electrons.'

(c)

Predict the product that results from the following 'pushed electrons.'

(f)

Predict the product that results from the following 'pushed electrons.'

(i)

Given the structure, calculate the index of hydrogen deficiency (degrees of unsaturation) of the following molecules.

(a)

What is the index of hydrogen deficiency for each of the following molecular formulas?

(a) C₆H₁₂O₆

What is the index of hydrogen deficiency for each of the following molecular formulas?

(b) C₁₂H₁₁NO₃

What is the index of hydrogen deficiency for each of the following molecular formulas?

(c) C₈H₁₄Cl₂

What is the index of hydrogen deficiency for each of the following molecular formulas?

(d) C₉H₁₂N₂O₂

What is the index of hydrogen deficiency for each of the following molecular formulas?

(e) C₆H₁₂O₂

Draw the molecular orbital picture of trans-but-2-ene.

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(d)

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(b)

Provide the IUPAC names for the following alkenes.

(a)

Given the following IUPAC names, draw the corresponding structures.

(a) (R)-3-isopropyl-6-methylnon-1-ene

Given the following IUPAC names, draw the corresponding structures.

(c) (S)-3-fluoropent-1-ene

Name the following alkenes, being sure to specify whether they are cis or trans.

(a)

Name the following alkenes, being sure to specify whether they are cis or trans.

(c)

Which of the following alkenes are E and which are Z?

(a)

Which of the following alkenes are E and which are Z?

(b)

Which of the following alkenes are E and which are Z?

(c)

Given the name, draw the structure of the following alkenes.

(a) (E)-4-ethyl-5-methyloct-3-ene

Given the name, draw the structure of the following alkenes.

(b) ((Z)-1-cyclohexyl-2-methylhept-2-ene

Given the name, draw the structure of the following alkenes.

(c) (Z)-3-isopropylhept-3-ene

Name the following alkenes.

(b)

How many stereoisomers are possible (a) for 4-methylnona-2,7-diene? (b) For 6-chloronona-2,4,7-triene?