11.12: 13.12 Additional Exercises

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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.

Thiols (Mercaptans)

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.