1) What is the major product of the following reaction?
HBr
Br
H
+
Br
Br
2) What is the major product of the following reaction?
HBr
peroxide
H
Br
Br
Br
Br
3) What is the major product of the following reaction?
1. Hg(OAc)2, H2O
2. NaBH4 , HO–
H
O
+
+
HgOAc
H
HgOAc
HgOAc
HOH
OH
OH
NaBH4
HgOAc
4) What is the major product of the following reaction?
Br2
CCl4
Br
Br
Br
Br
Br
Br
5) What is the major product of the following reaction?
HBr
H
H
Br
Br
Br
6) What is the major product of the following reaction?
HBr
peroxide
Br
Br
H
Br
Br
7) What is the major product of the following reaction?
Cl2
CCl4
Cl
Cl
Cl
Cl
Cl
Cl
8) What alkene should be used to synthesize the following alkyl
bromide?
Br
H
+
Br
Br
9) What alkene should be used to synthesize the following alkyl
bromide?
H
Br
Br
Br
10) What alkene, when allowed to react with HBr, would produce
the following alkyl bromide? (There is more than one correct
answer.)
H
Br
Br
Br
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?
Br
H
Br
Br
Br
H
Br
Br
Br
1) Give the kinetic product of the following reaction.
HCl
Cl
H
Cl
Cl
2) Give the thermodynamic product of the following reaction.
HCl
Cl
H
Cl
Cl
3) Give the major product of the following reaction.
HCl
Cl
H
Cl
Cl
4) Give the products of the following reaction.
Br2
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
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
H
Br
Br
Br
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.
HBr
H
Br
Br
Br
7) Draw the major product of the following Diels-Alder reaction,
including its stereochemistry where appropriate.
heat
+
O
O
O
8) Draw the major product of the following Diels-Alder reaction,
including its stereochemistry where appropriate.
heat
+
N
N
N
9) Draw the major product of the following Diels-Alder reaction,
including its stereochemistry where appropriate.
O
heat
+
O
H
H
O
O
O
O
10) Draw the major product of the following Diels-Alder
reaction, including its stereochemistry where appropriate.
N
heat
+
N
N
N
N
N
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.
O
O
+
heat
O
O
O
O
H
O
O
O
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.
O
Ph
O
Ph
O
Ph
13) Draw the diene and the dienophile required to prepare the
following compound by a Diels-Alder reaction
CO2CH3
CO2CH3
CO2CH3
14) Draw the diene and the dienophile required to prepare the
following compound by a Diels-Alder reaction
O
H
H
O
O
O
O
O
H
H
15) Draw the diene and the dienophile required to prepare the
following compound by a Diels-Alder reaction.
O
O
O