Textbook: Vollhardt 6th Ed. (2010)

Chapter 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 348

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

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 # 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 # 319

For a molecule to undergo an E2 reaction, the leaving group and the beta-proton must be in an anti-coplanar conformation (one atom straight up, the other straight down). Based on this, which compound undergoes E2 reaction with KOtBu faster? Why?

 

Problem # 341
 

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

Problem # 531

 

E2 elimination reactions require anti-coplanar geometry. (note: some textbooks call this anti-periplanar).
Let's work through an E2 reaction, and rotate the molecule eblow into an anti-coplanar geometry to predict the product of this E2 reaction.

 

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.