1) What is the major product of the following reaction? HBr

2) What is the major product of the following reaction?

3) What is the major product of the following reaction? 1. Hg(OAc) 2, H 2 O 2. NaBH 4, HO –

4) What is the major product of the following reaction? Br 2 CCl 4

5) What is the major product of the following reaction? HBr

6) What is the major product of the following reaction? HBr peroxide

7) What is the major product of the following reaction? Cl 2 CCl 4

8) What alkene should be used to synthesize the following alkyl bromide?

9) What alkene should be used to synthesize the following alkyl bromide?

10) What alkene, when allowed to react with HBr, would produce the following alkyl bromide? (There is more than one correct answer.)

11) What five-carbon alkene will give the same, single product whether it reacts with HBr in the presence or the absence of a peroxide?

1) Give the kinetic product of the following reaction. HCl

2) Give the thermodynamic product of the following reaction. HCl

3) Give the major product of the following reaction. HCl

4) Give the products of the following reaction.

5) Draw the major product of the following reaction, including its stereochemistry. (Use squiggly bonds to indicate a reaction that is not stereoselective.) Assume only one equivalent of the reagent is available to react with the substrate.

6) Draw the major product of the following reaction, including its stereochemistry. (Use squiggly bonds to indicate a reaction that is not stereoselective.) Assume only one equivalent of the reagent is available to react with the substrate.

7) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate.

8) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate.

9) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate.

10) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate.

11) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate. (The Diels-Alder reaction of anthracene with maleic anhydride is a common organic lab experiment.

If your dienophile is disubstituted (substituted twice), there is the possibility for stereochemistry in the product. In the Diels-Alder reaction, you end up with the stereochemistry that you started with. In other words, if the substituents started cis (on the same side) on the dienophile, they end up cis in the product. If they started trans (opposite sides) on the dienophile, they end up trans in the product.

When the diene is in a ring, the product of the Diels-Alder reaction is a bicyclo ring system (which can be somewhat intimidating to draw at first). A bicyclo ring system is a compound in which two rings share more than two carbons. There are two main bicyclo ring systems that you typically have to deal with, and these are the ones that come from the diene being in a five-membered ring system and the diene being in a six-membered ring system.

When you make bicyclic products (that is, when the diene is in a ring), and you have a dienophile that is substituted, there are two possible products that you can form from the Diels-Alder reaction--the endo product, in which the substituent points down from the top of the bicyclic molecule, and the exo product, where the substituent points towards the top of the bicyclic molecule. In general, you form the endo product preferentially over the exo product in the Diels-Alder reaction.

12) Draw the diene and the dienophile required to prepare the following compound by a Diels-Alder reaction.

13) Draw the diene and the dienophile required to prepare the following compound by a Diels-Alder reaction

14) Draw the diene and the dienophile required to prepare the following compound by a Diels-Alder reaction

15) Draw the diene and the dienophile required to prepare the following compound by a Diels-Alder reaction.