Textbook: Loudon 5th Ed. (2009)

Chapter 9: The Chemistry of Alkyl Halides

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 534

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

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 # 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 # 348

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 # 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 # 535
 

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

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 # 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 # 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.