9, 12, 15-21, 23-24

Ch 13 HW .

9)

ai
at

(2)
hehehehehehaHOH
OH OH
C 1 b C b 1 b C

CH3 CheHe He is
a a

CH3CHzCCHzCH3

c Ch
.)
15
A comp 2
Impound
: .

O
17 10
42
.

H-0-CHzCHzCH3
.
.

81 .

B : C 3
Impound .

H
( 1
impound
C :
.

2 0 ,9

ChyC-o-cichs
.

16 )
.
Each have index of deficiency of 1 ,
in the form of a double bond as evidenced by rxn W/DE.
0 .
9
17)
9
CH3 1 9
It
deficiency
=

,
.

0 .
.

CD
., CH3 CH-CH - no rings
1 . no double bonds
OH
group
as
-

CG
. . i 35
Ch
0 9 .
I *
.

1 6 1 7
CH3 CIt
.

CH
.
, -
- -

CE .

0 9 2 0
.
S ..
CH3 1%
:

ol
1 6, 1 7
.

. .

S
-CH C CH3
CHy-CHy
= -

C H.
C F.: dis .

i
.
08 . 13
.
so
20 4-3.
HyC CHz-CH 13

as
.

CHyCHzCHCH20 H .t
2

0- 9
. .

- 9 . 1 41
.
4
.
1 55
.

36 . 29
.

CI .
.

(HyCHeCHeCH2CHzOH
3) Carbon 2/w-OH) isachiral center
atom That makes -
two methyl
are complex
.

groups diasteritopic so signals ,

2 75 13
c) Carbon atom 2 is a chiral center .
-> makes adjacent -

Che protons
18 )
.
.

H CH3 diasterotopic =
complex signals
.
va
-
HX I
24
. .o

10) ( =
c!

19) H .
. deficiency of 0
H
"
1 3
.
21. ) H deficiency of
.
1
-
no rings CH3
-
H(c
"
bonds

/
no it
c Chy'
7=
-
-
=

H
1 38
H
.

OH
1 HS I 148 9

[Hy(Hn(CHz2 He
2 1

thydrogenation
. . .

CH3" OH

K2
CHy-CH-H
dehydration of compound
(Comp )
.

CH3)y
(compound N)
- C
= y
HI CH2CHe