Show how you would synthesize the following alcohol from appropriate alkene.

(b)

Show how you would synthesize the following alcohol from appropriate alkene.

(d)

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(a) octan-3-ol from hexanal, CH₃(CH₂)₄CHO

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(d) 2-cyclohexylethanol from bromocyclohexane

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(e) benzyl alcohol (Ph–CH₂–OH) from bromobenzene (Ph–Br)

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(g) cyclopentylphenylmethanol from benzaldehyde (Ph–CHO)

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(b)

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(c)

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(d)

Show how you would synthesize the following:

a. 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent

Show how you would synthesize the following:

c. cyclohexylmethanol from an alkyl halide using an S_N2 reaction

Show how you would synthesize the following:

e. cis-pent-2-en-1-thiol from a suitable alkenyl halide

Show how you would synthesize the following:

f. 2,5-dimethylhexane from a four-carbon alkyl halide

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(d)

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(e) (CH₃)₃C–O^– + CH₃CH₂OH ⇌

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(f) (CH₃)₃C–O^– + H₂O ⇌

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(g) KOH + CH₃CH₂OH ⇌

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(a) octan-1-ol

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(b) 1-cyclohexylpropan-1-ol

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(c) 1-phenylbutan-1-ol

(d)

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(e)

(f)

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(a)

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

Geminal diols, or 1,1-diols, are usually unstable, spontaneously losing water to give carbonyl compounds. Therefore, geminal diols are regarded as hydrated forms of ketones and aldehydes. Propose a mechanism for the acid-catalyzed loss of water from propane-2,2-diol to give acetone.

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(a)

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(b)

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(c)

Compound A (C₇H₁₁Br) is treated with magnesium in ether to give B (C₇H₁₁MgBr), which reacts violently with D₂O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH₃COCH₃) followed by hydrolysis gives D (C₁₀H₁₈O). Heating D with concentrated H₂SO₄ gives E (C₁₀H₁₆), which decolorizes two equivalents of Br₂ to give F (C₁₀H₁₆Br₄). E undergoes hydrogenation with excess H₂ and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Determine the structures of compounds A through G, including stereochemistry where appropriate.