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

Chapter 4: Alcohols and Alkyl Halides

Practice Problems and Mendel Sets

Individual Problems

Problem # 1287
 

Rank each set of compounds in order of decreasing boiling point (1 = highest boiling point):

a) ethane, n-octane, n-pentane

b) n-butane, 1-butanol, 1-chlorobutane.

c) n-octane, 2-methylheptane, 2,5-dimethylhexane

 

(Note that the n- prefix before an alkane just means that it's one chain, without any branching.)

Problem # 331

Rank the carbocations below in order of decreasing stability. (1 = most stable)

Problem # 332

Each of the carbocations below will spontaneously rearrange. Draw the structure of the expected rearrangement product.

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 # 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 # 347

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

Problem # 518
 

The alcohol below is protonated and contains an oxygen with a positive charge. Using curved arrows, show the two "legal moves" that result in a neutral oxygen.

Problem # 346

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

Problem # 697

Rank the following compounds in order of decreasing boiling point.

Also, make a guess about their relative solubilities in water. Explain your reasoning.

Problem # 321
 

Using curved arrows, draw a mechanism for the SN1 reaction shown below.

 

Problem # 322
 

Using curved arrows, draw a mechanism for the SN1 reaction shown below.

Problem # 337
 

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

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?

Mendel Sets

MS 899 - Beginning Mechanism Practice Submitted by Matt on August 6, 2011.

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

Keywords: carbocation rearrangement, free radical halogenation, mechanism

Description: Practice mechanisms from the first half of Fall semester orgo. Dehydration (E1), substitution with carbocation rearrangement (SN1), and free-radical bromination.

Total Problems: 3

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