Textbook: Loudon 5th Ed. (2009)

Chapter 10: The Chemistry of Alcohols And Thiols

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 519
 

Let's work through an elimination reaction. Draw the structures for each of the species in the three boxes below (protonated thiol, carbocation, and alkene). Also draw curved arrows to show electron movement. 

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 # 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 # 333

Let's go over how a carbocation can form from an alcohol.

Write in the curved arrows to show the formation of the protonated alcohol, and water acting as a leaving group to form a carbocation.

Problem # 348

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

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 # 677

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

Problem # 341
 

 Predict the product(s) of the reaction below, and used curved arrows to show a mechanism.

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.