Problems 179
- Draw curved arrows to show the flow of electrons responsible for the conversion of reactants into products.
- Give the reagents that would be required to carry out the following syntheses:
- For each pair of bonds, which has the greater strength? Briefly explain why.
a. c.
b. d.
- Give the major product of each of the following reactions:
- Using any alkene and any other reagents, how would you prepare the following compounds?
a. c. e.
b. d. f.
- There are two alkenes that react with HBr to give 1-bromo-1-methylcyclohexane.
a. Identify the alkenes.
b. Will both alkenes give the same product when they react with HBr/peroxide?
c. With HCl?
d. With HCl/peroxide?
CH 3 CH 2 CHCHCH 2 CH 3
BrCl
CH 2 CHCH 3
OH
CH 3 CH 2 CH 2 CHCH 3
Cl
CH 3 CH 2 CHCHCH 2 CH 3
BrOH
CH 2 Br
HCl
a.
Br 2
b. CH 3 OH
H 2 O
c.
d. H
+
H 2 O
e. HBr
peroxide
f. HBr
Cl 2
g. H 2 O i.
H+
CH 3 OH
j. HCl
peroxide
h.
Cl 2
CH 2 Cl 2
CH 3 CH 2 CH 2 IBror BrBr
H
or CH 3 CHCH 3
H
CH 3 Cl or CH 3 Br CH 3 CH 3 or CH 3 CH 2 CH 3
CH 2 CH CH 2
CH 2 CH 2 CH 2 OH
CH 2 CHCH 3
CH 2 CHCH 3
CH 2 CHCH 2 Br
CH 2 CH 2 CH 2 Br
CH 2 CHCH 3
CH 2 CH 2 CH 3
CH 2 CHCH 2 Br
OH
OH
Br
Br
OCH 3
a.
b. CH 3 C C
+
+
c. CH 3 CH 2 +
CH 3
CH 3 CH 2 Br–
C OCH 3
O–
CH 3
CH 3 C CH 3
O
CH 3 O–
H CH 3 C C– + NH 3
Br CH 3 O– OCH 3 +
