Chapter 8 Part 1 Review Sheet, Alkene Reactions

1) Predict the major product(s) for the following reactions.

itohi
H2SO4 加成
亲电
a)
合⼀
H 2O

1) BH3 叫

()
b) ~
2) NaOH / HOOH

的
规则

1) Hg(OAc)2 / H2O
羟汞化
⾯下
c)
2) NaBH4
,

⾅
Br2

简鱡
d)
CCl4
客 br

·
e)
Cl2

CH3OH
艌
1) OsO4

(斯
f)
顺域
2) Na2SO3

innrònvrtt
1) m-CPBA
g)
2) H3O+ / H2O

蛷
皉成
 䝃 ⼼ LH

h)
CHCl3

KOH
讞
H2

()
i)
Pd/C 注意是 顺式 加成 ,

⼈。
1) O3
j)
ii. 2) S(CH3)2 t.to

9
KMnO4 - tu
ˊ \
bubvlikooahoH.H.io
k)
H3O+
H

H2

纞
l)
Pd/C

iii. 向樵
H2SO4
m)
H 2O

S~ig.u.si
R

H2SO4
n)
CH3OH

o) H2SO4

tifosomlR.SI
HO
,
 i
2) Write a stepwise mechanism for the following reactions showing ALL intermediates. Use curved
arrows to symbolize the flow of electrons to show how each of the intermediates and product are
formed. Show all lone pairs and formal charges.

OH
Cl2
a) OH
H 2O Cl Cl
嶋

nj-Y-D://t.tl 14
1
11 C
1
-

D爣
1-
OCH3
向㘛 "
"
们

cl.int
H2SO4
b) ,

HOCH3

的 ⼀⼝ieg
器 以

⼀
留
- 谼
_
 t.

OH O
c) 1) Hg(OAc)2 / H2O

2) NaBH4

]
"
叫 f
⼋ ,

愈
强
龤⾕
i n
。

0
t 0Ac
1
1

d)
O
H3O+

H 2O
O
H
EQIYHghc.IN 。
1314

蠱步
nduts.li
⼗

能⼀⽇撬
→
㡩得
3) The following reactions are all INCORRECT. Explain using words and structures why it is
incorrect and write the correct answer.

OH Correct Product:
1) BH3
a)

()
^
2) NaOH / HOOH 0H

的 规则
。

Correct Product:
1) OsO4 OH
b)
2) Na2SO3 鳅
OH
-o
H

顺式

Br2 Br Correct Product:

tmr
c)
CCl4
Br

顺式
4) Predict the reagent(s), in order, to convert the given starting material ((1Z)-1methyl-1-cyclohexene)
to the products specified below. It may require multiple steps to do the conversion and you may use
any reagents necessary.
Br OH

a) b) c)

OH
d) e) f)
Br OH

OH
OH
g) h) i)
Br OH OH

O O
j) k) OH

Structure Reagent(s)
a H Br _

b 从0 个 301
① 的 04
c ②
lgoAdzlHWNa.it
d

e
Heat.Hz.pdlcBn.HN 。

BH3.DNaotyHO H -Br.NOYHOr.DQG.DZ/VazSgDmCPBAJHjM
f ①

i
。
j +
0了
Sccrhhhn
C
,

k
04 Hi
5) Fill in the boxes with the necessary reagents (1-3) or the major product (A-K).

NOTE: A-K are all different structures

代
C C5H10Cl2
"
2 NaNH2 / NH3
⼼
D C5H8

Cl2 / CCl4

消去
⻢⽒
hr
.

Br
1
⼼ 1) Hg(OAc)2 / H2O

A C5H10
2) NaBH4
B C5H12O 651
2 3
加成
消去

公 ⼼
E C5H12O F C5H10

HCl Br2 / H2O

⼈ ⼼ NaCN
⼤些

ICN.tk
DMF
G C5H11Cl 么 H C5H11OBr
br .

I C6H11ON

B + NaH NaH

O
H3O+

H 2O
J C5H10O K C5H12O2

^ 01 -
1 - ^0 0
-
>
^o^ .
 -

6) The compounds shown below are products of cleavage reactions. Determine the structure of the
starting material for these reactions.
Structure

a) A
C8H14 01) O3

2) S(CH3)2
O

O
2
H
O

H
in

b)
B
C7H12
1) O3t.fi
2) S(CH3)2
O O

H 分
O O O
C
in
KMnO4
OH OH
c) H3O+
O
H2 / Pd/C
HO OH
2-methyl-hexane

d) D
C 6H 8
KMnO4

H3O+
HO
O O

OH
向
7) We have learned the first step of hydroboration is a concerted reaction as shown below.

One step mechanism; concerted mechanism

H
H B
H B H H H
H H

Another proposed mechanism for hydroboration is two step mechanism, where there is an
intermediate. Why isn’t this the correct mechanism, how can you prove that this isn’t the correct
mechanism? Hint: Think about modifying the structure of alkene in this reaction in order to
determine which mechanism is correct.

Two step mechanism with intermediate

Q
H H
H B B
H H B H H H H H H
H