Textbook: Solomons 10th Ed. (2009)

Chapter 6: Ionic Reactions

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 534

Using curved arrows, draw the mechanism for the SN2 reaction below.

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 # 348

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

Problem # 535
 

Rank the following anions in order of decreasing stability (1 = most stable)

Problem # 536

Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)

Problem # 537
 

Indicate the reagents necessary to carry out each transformation.

Problem # 538
 

Rank the following electrophiles in order of decreasing reactivity with NaN3 in DMF. (1 = most reactive)

Problem # 539

Rank the following compounds in order of decreasing nucleophilicity. (1 = most nucleophilic)

Problem # 540

 

Rank the following anions in order of decreasing stability (1 = most stable)

Problem # 331

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

Problem # 541
 

Rank the following compounds in order of decreasing reactivity with NaI in acetone. (1 = most reactive)

Problem # 332

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

Problem # 542

 

Rank the following compounds in order of decreasing reactivity with water (solvolysis). (1 = most reactive)

Problem # 560
 

For each reaction below, determine whether the primary reaction is SN1, SN2, E1, or E2, and then draw the product.

Note: Me = methyl (CH3)

Problem # 703

Show two ways to prepare the ether below from a combination of an alcohol and an alkyl halide via the Williamson ether synthesis.

Is one way better than the other? Why?

Problem # 337
 

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

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.