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

Chapter 8: Nucleophilic Substitution

Practice Problems and Mendel Sets

Individual Problems

Problem # 534

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

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 # 541
 

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

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?

Mendel Sets

MS 908 - SN1-SN2-E1-E2 Review Submitted by Matt on August 6, 2011.

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

Keywords: leaving groups, nucleophilicity, SN1/SN2/E1/E2

Description: Goes through substitution and elimination competition reactions:

  • Nucleophile strength trends
  • Leaving group trends
  • Steric effects
  • How to tell the difference between SN1, SN2, E1, and E2 reaction conditions

Total Problems: 10