Physical Properties of Alcohols
13-1 Identify which compound is more acidic. Explain your reasoning for each choice.
13-2 Identify which is the most acidic proton in the following compounds. Explain your reasoning for each choice.
13-3 Draw all possible resonance forms of the conjugate base of phenol.
13-4 List the following compounds in order from most to least acidic.
13-5 Predict which compound of each pair is more soluble in water and explain your reasoning.
butan-1-ol or pentan-1-ol
phenol or cyclohexanol
octan-1,3-diol or octan-1-ol
1-chlorohexane or hexan-1-ol
13-6 Predict which compound has the higher boiling point and explain your reasoning.
water or ethanol
butan-1-ol or octan-1-ol
hexan-2-ol or hexan-2-one
Synthesis of Alcohols
13-7 Show a possible way to synthesize the following alcohols.
13-8 Give the product of each reaction.
13-9 Give the product of each reaction.
13-10 Give the product of each reaction.
13-11 Give the product of each reaction.
Organometallic Reagents for Alcohol Synthesis
13-12 Draw the products of the following reactions.
13-13 Draw the products of the following reactions.
13-14 What is the final product of the following reaction.
13-15 Draw the mechanism for question 13-14.
13-16 Identify the product of the following reaction and explain why that is the correct answer.
Addition of Organometallic Reagents to Carbonyl Compounds
13-17 Give the product(s) of the following reactions. Include stereochemistry when necessary.
13-18 Show a possible carbonyl compound that was used to make the following alcohols through a Grignard reaction.
13-19 For the following compounds, identify the Grignard reagent used and the initial methyl ester compound.
13-20 Give the products of the following reactions.
Reduction of the Carbonyl Group
13-21 Identify whether the initial compound is undergoing oxidation or reduction.
13-22 Give the product of each reaction.
13-23 Give the product of each reaction (same starting molecule), making sure to specify where each proton ends up in the final product.
13-24 Give the mechanism for the following hydride reduction reaction.
13-25 Draw the structures for A and B.
13-26 Name the following compounds following IUPAC nomenclature.
13-27 Identify the product of the following reaction. Include stereochemistry if appropriate.
13-28 Identify the product of the following reaction.