Textbook: Carey and Giuliano 8th Ed. (2010)

Chapter 15: Alcohols, Diols, Thiols

Practice Problems and Mendel Sets

Individual Problems

Problem # 701

The acid-catalyzed condensation of alcohols to form ethers is reversable; ethers can be hydrolyzed back to alcohols. How can the direction of this equilibrium be controlled to preferentially form ethers?

Problem # 678

Draw the structure of the major organic product from each reaction sequence.

Problem # 347

For the reaction below, draw the structures of the carbocation intermediate and the final product.

Problem # 677

Show a mechanism for the acid-catalyzed cyclization (condensation) of 1,4-butanediol.

Problem # 674

Show a mechanism for the reduction of butyrolactone using LiAlH4.

Problem # 673

Show how each compound can be prepared from an alkene containing 3 carbons (or less).

Each answer will involve the reaction of a Grignard with either a carbonyl or epoxide.

Note: epoxides are prepared from alkenes using a peroxy acid (epoxidation) such as mCPBA.

Problem # 679

Compound A (C5H12O) is oxidized using aqueous chromium (Jones reagent) to compound B (C5H10O2), which is then treated with methanol under acidic conditions to yield compound C (C6H12O2) and water.

The 1H NMR of compound C is shown below. Determine the structures of compounds A, B, and C.

Mendel Sets

MS 917 - Alcohol and Carbonyl Redox Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 15

Keywords: alcohols, hydride reduction, oxidation

Description: Goes over how alcohols can be oxidized to form aldehydes/ketones and carboxylic acids, which can be transformed further using Grignard reagents, hydride reagents such as NaBH4, and by performing Fischer esterification. Includes several synthesis problems involving carbonyls and epoxides. Also includes an NMR based problem.

Total Problems: 5