6

6.1

6.3

6.4

6.5

6.6

6.7

6.8

6.9

6.10

6.2

p.179

mirror images

sp3-

p.179

p.179

6.1 CH3X CH2XY

CHXYZ
CHXYZ

6.1

6.1 CH3X , CH2XY CHXYZ

CH3X
CH2XY

CHXYZ

p.180

p.180

enantiomers

p.180

6.2 (a) H OH
CO2H CH3 (b) CO2H
CH3 H OH

p.181

6.2
chiral

chirality centersstereocenters

5-
5-bromodecane C5

p.181

p.181

nonchiral
achiral

p.181

p.182

 6.3 (a)
(b)

p.182

6.2

6.1

p.182

6.2

3-

OH
H,
OH, CH3 CH2CH3

3- CH2
CH3

p.182

C3 H , CH3 , CH2 CH3 CH2 CH2 CH3

p.183

6.3

6.3
2-

Jean Baptiste Biot

CH3 CH2 C=O

C2
C2 CH3 H
C=O CH2 2-

p.183

optically active
polarimeter

6.5

p.184

 6.5

levorotatory
dextrortatory
(2)
(1)
(2)- (1)-
6

p.184

p.185

specific rotation[a ]D 589.6

nm1nm 10 9 m l
l dm1 dm 10 cm c 1g/cm3

[a]D
6

p.185

6.4

6.4
1.20 g cocaine[a ]D16 7.50
mL 5.00cm

Biot 1848

p.185

p.185

Louis Pasteur

28C

6.6

p.186

 6.6

6.5

configuration

p.186

p.187

6.7

123
R R configuration
rectus 123
S S
configuration sinister

p.187

6.7
4
123
R 123
S

p.187

p.187

6.8 (a) (R)-()- (b) (S)-()-

p.188

 6.9 (a) ()- (b) ()-

S

6.5 R S

R S

180

p.189

6.5 ()

6.6

p.189

p.190

6.6

(1) Cl(2) CH2CH3(3) CH3(4)
H H

123

90

p.189

(b)
3
1 2
R

(R)-2-

6.5 ()

(a)
2 3 1
R

p.190

n 2n

2--3-C2 C3

22 4 6.10

p.191

 6.10

2--3-

diastereomers

6.2

p.191

p.191

6.7

p.192

2R,3R 2S,3S

p.193

2R,3S 2S,3R

2R,3S 2S,3R
180

C2C3
6.11
6.11

mesocompounds

p.193

p.193

 6.11 C2C3

6.3

(1)(2)

(1)(2)

p.194

6.7

p.194

6.7 ()

-1,2-

p.194

-1,2-
C1 C2 C1
C2
-1,2-

p.194

6.8

RCO2H

2R,3R 2S,3S

--

RNH2

5050
racemic mixtureracemate
d,l

p.195

p.195

 6.12

p.196

6.13 (R)-1-

6.8

p.196

6.8

10.6 RCO2HR
OH
RCO2R
()- CH3OH

p.197

6.9

p.197

6.14

constitutional isomers2.2

stereoisomers2.8

p.197

p.198

 6.14

p.198

p.198

6.10

1,8-limonene()
()

p.199

p.199

fluoxetine
Prozac
fluoxetine
S

6.15

p.199

p.200

10

 6.15
(a)

p.200

6.15 (b)

p.200

6.16

NAD
CH3CHO
CH2
6.16a

6.16b
OHCH3
Hb
Ha

p.200

p.201

V
Penicillium
2S,5R,6R

p.201

p.201

11

 ()

()

Ibuprofen
AdvilNuprin Motrin 5050 R S
S
R
S

p.202

p.202

12