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.