Identify the alkene and alcohol partners that could be used to make the following ethers.

(c)

Predict the products of the following reactions.

(a)

Predict the products of the following reactions.

(b)

Predict the products of the following reactions.

(c)

Show an arrow-pushing mechanism that rationalizes formation of the two products. Which C―O bond will break first? Why?

Predict the alcohol and haloalkane that will form upon reaction of the ether shown with one equivalent of HBr. [Hint: Think carefully about which side will become the halide.]

Methyl t-butyl ether (MTBE) is used preferentially over diethyl ether because it is less prone to form peroxides. Explain this observation in terms of the two structures.

Predict the product of the following reactions.

(a)

Predict the product of the following epoxide addition reactions.

(a)

Predict the product of the following epoxide addition reactions.

(b)

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(b)

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(c)

Reaction of the acetylide with the epoxide shown will not form the desired product. What side reaction occurs instead? Why?

Show how a protecting group might be used to make these reactions successful.

(a)

Show how a protecting group might be used to make these reactions successful.

(b)

Using IUPAC rules, name the following molecules.

(b)

Using IUPAC rules, name the following molecules.

(d)

Using IUPAC rules, name the following molecules.

(e)

Draw the correct structure from the following IUPAC names:

(a) (4R,2Z)-4-methylhex-2-en-1-ol

Draw the correct structure from the following IUPAC names:

(b) 4-methoxybut-1-yne

Draw the correct structure from the following IUPAC names:

(c) (1S,4R)-4-bromocyclohex-2-en-1-ol

Draw the correct structure from the following IUPAC names:

(d) (2R,3S)-methoxy-3-methylpentane

Draw the correct structure from the following IUPAC names:

(e) (R)-2,2-dimethyl-1-phenylpropane-1-thiol

Draw the correct structure from the following IUPAC names:

(f) (S)-4-isopropoxypent-2-yne.

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.'

(a)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH₃ 2. NaOH, H₂O₂. If there is no reaction, write 'no reaction.'

(a)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H₂O. If there is no reaction, write 'no reaction.'

(a)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO₄ 2. NaHSO₃. If there is no reaction, write 'no reaction.'

(a)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (vi) NaOH, H₂O . If there is no reaction, write 'no reaction.'

(a)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iii) H₂SO₄ , H₂O . If there is no reaction, write 'no reaction.'

(a)