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

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

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

3 3) What is the major product of the following reaction? 1. Hg(OAc) 2, H 2 O 2. NaBH 4, HO +HgOAc+HgOAcHOHOHHHgOAcOHHgOAcNaBH4OH

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

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

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

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

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

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

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

11 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? HBrBrBrBrBrHBrBr

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

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

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

15 4) Give the products of the following reaction. Br2 BrBrBrBrBrBrBrBrBrBr

16 BrBrBrBrBrBr

17 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. HBr HBrBrBr

18 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 HBr available to react with the substrate. HBrBrBr

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

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

21 9) Draw the major product of the following Diels-Alder reaction, including its stereochemistry where appropriate. O+Oheat OOHHOO

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

23 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. +OOOheat OOOOOOH

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25 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.

26 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.

27 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.

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

30 13) Draw the diene and the dienophile required to prepare the following compound by a Diels-Alder reaction CO2CH3 CO2CH3CO2CH3

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

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