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11.12: 13.12 Additional Exercises

  • Page ID
    183001
  • 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.

     

    1. butan-1-ol or pentan-1-ol

    2. phenol or cyclohexanol

    3. octan-1,3-diol or octan-1-ol

    4. 1-chlorohexane or hexan-1-ol

     

    13-6 Predict which compound has the higher boiling point and explain your reasoning.

     

    1. water or ethanol

    2. butan-1-ol or octan-1-ol 

    3. 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.