Textbook: Loudon 5th Ed. (2009)

Chapter 5: Addition Reactions of Alkenes

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 1336
 

Determine a synthesis to prepare 2-chloro-4-methylpentane from 1-iodo-4-methylpentane.

 

          from         

Problem # 346

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

Problem # 334

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

Use curved arrows to show the two carbocations that can from from 1-methylcyclohexene.

 

Problem # 335

Carbocations aren't very stable and so don't last very long after they are formed.

Use curved arrows to show:

a) how a carbocation reacts with a halide ions to form an alkyl halide.

b) how a carbocation reacts with water to form an alcohol.

c) how a carbocation reacts with a base to form an alkene.

Problem # 336
 

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

Problem # 342

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

 

Problem # 343

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

Problem # 344

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

Problem # 345

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

 

Problem # 520
 

Let's work through an alkene addition reaction. Draw the structures for each of the species in the three boxes below (3º carbocation, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.

 

Problem # 529

Indicate the major organic product of the reaction below. Include stereochemistry.

Problem # 530

 

Let's work through anti and syn additions to alkenes.
Show the product for each reaction below, and indicate whether the product will be a racemic mixture of enantiomers, or a meso compound (which is achiral).

Problem # 324
 

Using curved hooks, draw a mechanism for the free radical bromination  reaction shown below.

Problem # 1280
 

The structure of 2-methylbutane is shown below.

a) Draw the structures of all possible monochloro products resulting from the free-radical chlorination of 2-methylbutane.

b) Based on statistics alone, what do you expect the major product to be? Is this the same structure as the expected major product? Explain.

c) How would the relative yield of the products differ if bromine was used instead of chlorine?

Problem # 521
 

Let's work through a halogenation reaction. Draw the structures for each of the species in the four boxes below (3º carbocation, halonium ion, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.