Page 589 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

570 5.2. Predict the structure, including stereochemistry, of the product(s) expected for
the following reactions. If more than one product is shown, indicate which is
CHAPTER 5
major and which is minor.
Polar Addition
and Elimination a.
Reactions
CH OH
2
Br 2
Ph C CH 2 CH CH 2 C H O Br
2
12 15
CH OH
2
b.
DCl
C 6 H 8 DCl

c.

O
NaOEt
erythro-ArCCHCHAr C H Cl O
3
15 9
EtOH
Cl Cl
d.

H 2 O
(CH 3 ) 2 C
CH 3 C 10 H 18
heat
+
(CH 3 ) 3 N
e.
CH CH 3
3
CH Cl 2
C C 3 C 11 H 17 Cl
CH
3 CCl 4
CH 3
CH 3
f.
CH 3 KOC(C H )
2 5 3
Cl

g.

1) Hg(OAc) 2
CH 3 OH
CH 3 CH=CH 2 C H ClHgO
10 13
2) NaCl