Textbook: McMurry 8th Ed. (2011)

Chapter 8: Alkenes: Reactions and Synthesis

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 1336
 

Determine a synthesis to prepare 2-chloro-4-methylpentane from 1-iodo-4-methylpentane.

 

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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 # 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 # 336
 

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

Problem # 342

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

 

Problem # 343

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

Problem # 344

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

Problem # 345

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

 

Problem # 520
 

Let's work through an alkene addition reaction. Draw the structures for each of the species in the three boxes below (3º carbocation, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.

 

Problem # 521
 

Let's work through a halogenation reaction. Draw the structures for each of the species in the four boxes below (3º carbocation, halonium ion, protonated thiol, and thiol). Also draw curved arrows to show electron movement. Note: thiol = RSH, like an alcohol, but with sulfur instead of oxygen.

Problem # 529

Indicate the major organic product of the reaction below. Include stereochemistry.

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 # 530

 

Let's work through anti and syn additions to alkenes.
Show the product for each reaction below, and indicate whether the product will be a racemic mixture of enantiomers, or a meso compound (which is achiral).

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.