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

Chapter 6: Addition Reactions of Alkenes

Practice Problems and Mendel Sets

Individual Problems

Problem # 1336
 

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

 

          from         

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 # 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.

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).

Mendel Sets

MS 903 - Carbocation and Alkene Review Drills Submitted by Matt on August 6, 2011.

Textbook and Chapters: Carey and Giuliano 8th Ed. (2010), Chapters 4, 5, 6

Keywords: alkene addition, carbocation

Description: Identify the intermediates (carbocation, radical, borane intermediate, etc.) and products for important reactions dealing with alkenes. Good review for an orgo1 midterm.

Total Problems: 7

MS 904 - Carbocation Drills Submitted by Matt on August 6, 2011.

Textbook and Chapters: Carey and Giuliano 8th Ed. (2010), Chapters 4, 5, 6

Keywords: carbocation, carbocation formation, carbocation rearrangement

Description: This mendel set guides you through everything you have to know about carbocations:

  • Ways carbocations form
  • Carbocation rearrangements
  • How carbocations react (elimination or nucleophilic attack)

Also includes some practice problems: addition to an alkene, dehydration (E1), and substitution (SN1).

Total Problems: 8

MS 907 - Alkene Addition and Elimination Mechanisms Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 6

Keywords: alkene addition, carbocation, dehydration, E1 mechanism

Description: This mendel set is a complement to Carbocation Drills. It is meant to prepare students on how to approach longer and more complicated mechanisms. Reaction mechanisms covered:

  • Acid-catalyzed elimination (dehydration, E1)
  • Acid-catalyzed addition to an alkene
  • Halohydrin formation (halonium ions, which result in anti-additions.)

Total Problems: 4