In each case, circle the stronger nucleophile.

(b)

In each case, circle the stronger nucleophile.

(c)

In each case, circle the stronger nucleophile.

(d)

Identify the following reactions as oxidation or reduction (based on what happens to the organic molecule).

(a)

Identify the following reactions as oxidation or reduction (based on what happens to the organic molecule).

(b)

Identify the following reactions as oxidation or reduction (based on what happens to the organic molecule).

(c)

Based on the analysis you used in Assessment 17.3, which carbonyl would you expect to react most quickly with a nucleophile?

(a)

Based on the analysis you used in Assessment 17.3, which carbonyl would you expect to react most quickly with a nucleophile?

(c)

Give a structure that corresponds to the name provided.

d. E-4-oxopent-2-enal

Predict the product of the following aldehyde/ketone syntheses.

(a)

Predict the product of the following aldehyde/ketone syntheses.

(c)

Predict the product of the following aldehyde/ketone syntheses.

(d)

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(a)

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(b)

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(c)

Another way the preceding might be presented is to say that the minor resonance structure(s) reveal the reactivity of a molecule. Show how the minor resonance structure(s) can help us understand that the following reactions occur with the regioselectivity shown.

(a)

(b)

(c)

Identify the bonds broken and formed in the following addition reaction.

(a) Would you expect this reaction to be favored based on entropy?

(b) Based on enthalpy [qualitatively]?

(c) Overall?

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(a)

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

b)

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(d)

A student, when solving the following 'predict-the-product' question, made a common mistake by writing the answer shown here. Explain why this reaction would not work as written.

Suggest an acetylide ion and a carbonyl that might be used to make the following products.

(a) oct-4-yn-3-ol

Suggest an acetylide ion and a carbonyl that might be used to make the following products.

(b) 2,6-dimethylhept-3-yn-2-ol

Suggest an acetylide ion and a carbonyl that might be used to make the following products.

(c) 5-phenylhex-2-yn-1-ol

Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.

(a)

For each of the following carbonyl addition reactions, would you expect a racemic mixture or a mixture enriched in one stereoisomer? In each case, draw both possible stereoisomeric products.

(a)

Suggest the appropriate carbonyl and Wittig reagent to make the following alkenes.

a. (E)-7-methylnon-4-en-3-one

Identify the hemiacetal functional group in each of the following molecules. These molecules may not be stable enough to be the favorable product in an equilibrium reaction.

(c)

Provide a mechanism for the formation of the hemiacetals shown. [Only (c) is favored as written.]

(a)

Which of the following cyclic hemiacetals would you expect to have the highest K_eq for their formation? Explain your answer.

(a)