2302169 Chem Med Studt
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ส่งการบ้านที่กล่องรับ หน้ าห้อง 1326/7 ชัน้ 13 อาคารมหามกุฏ ภายในวันที่................................................
1) Label each pair of the following compounds as constitutional isomers, stereoisomers, or not isomers of
each other (different compounds).
O
1.1
O
and
1.2
and
O
O
CH 3
and
1.3
1.4
CH 3
and
2) On the basis of Cahn-Ingold-Prelog system, label each chiral center as R or S.
SH
2.1
H
2.2
H
CH3
CH3 CH 2
CN
H
H3 C
2.5
2.3
CH 3
D
T
Cl
2.6 Br
CH2 I
CH2 CH 3
H3 C
H
HO
HOOC
2.7 H3 C
HO
H
O
2.10
2 .17
2.13
2.14
O
OH
OH
2.8
Cl
2.12...........
2 .15
2.9
Cl
2.11...........
2 .16
O
2.11
NH 2
H
CH 3
2.10...........
OH
2.12
NH
2.4
2.9 ..........
CH 3
O
CH3
SH
configuration (R or S)
O
O
CH(CH 3 )2
O
2 .18
2.13...........
O
2.14...........
O
O
2.15...........
2.16...........
O
2.17...........
2.18...........
Paclitaxel: a chemotherapy drug usually given to treat ovarian, breast and non-small cell lung cancer
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 1 S t e r e o c h e m i s t r y , A l c o h o l , E t h e r a n d E p o x i d e
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3) Threonine is a natural occurring amino acid that contains two stereogenic centers. Draw all possible
stereoisomers and assign the R, S configuration to each isomer.
H 2N
H
COOH
H
OH
CH3
Threonine
4) How is each compound related to the simple sugar D-erythrose? Is it an enantiomer, diastereomer or
identical compound?
OHC
H
HO
OH
H
CH 2OH
OHC
HO
H
CH 2OH
H
OH
HOH2 C
HO
H
4.2
4.1
D-erythrose
CHO
OH
H
OHC
HO
H
H
OH
CH 2OH
OHC
H
HO
4.3
5) How are the compounds in each pair related to each other? (identical compound, enantiomers,
diastereomers, constitutional isomers or different compound)
and
5.1
CH 3
5.2
5.3
and
CH 3
H3 C
H
HO
CHO
OH
H
OHC
H
HO
and
and
5.4
and
5.5
Cl
Cl
Cl
5.6
I
Cl
Br
H
and
H
Br
I
CH 3
H
OH
H
OH
CH 2OH
4.4
2302169 Chem Med Studt
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5.7
H3 C
H
Br
CH 3
Br
H
H3 C
H
Br
and
H
Br
CH 3
H
5.8 HO
OH
HO
and
OH
H
H
H
and
5.9
H
5.10
BrCH2
CH 3
CH2 OH
CH 3
and
5.11
and
HOH 2C
H
BrCH 2
H
CH 3
CH3 H
5.12
HO CH 3
H
CH 2 Br
and
H 3C
Br
CH 2OH
H
6) The [α] of pure quinine, an antimalarial drug, is -165. Calculate the enantiomeric excess (ee) and % each
enantiomer present in the solution with the following [α] values.
6.1) -50
N
HO
H 3CO
6.2) -83
N
quinine
6.3) -120
2302169 Chem Med Studt
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7) Give the IUPAC name for each alcohol.
7.1
(CH3 )2 CHCH2 CH2 CH 2OH
7.2
(CH3 )2 CHCH2 CH(CH 2CH3 )CH(OH)CH 2CH3
7.3
7.4
HO
OH
HO
OH
7.5
OH
7.6
OH
(H 3 C) 2HC
OH
8) Rank each group in order of:
8.1) increasing boiling point:……………………………………………………
CH 3CH 2CH2OH
a
(CH 3) 2CHOH
b
CH 3CH 2OCH 3
c
8.2) increasing water solubility:…………………………………………………
CH 3(CH 2)5OH
a
HO(CH2)6OH
b
CH 3(CH 2)4CH 3
c
9) Draw the organic product(s) formed when CH3CH2CH2OH is treated with each reagent.
9.1 H2SO4
9.2 NaH
9.3 HCl + ZnCl2
9.4 HBr
9.5 SOCl2, pyridine
9.6 PBr3
2302169 Chem Med Studt
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9.7 TsCl, pyridine
9.8 [1] TsCl, pyridine; [2] NaSH
10) Identify compounds 10.1-10.6 in the following reactions
10.1
NaH
TsCl, pyridine
CH 3 I
10.2
10.3
CH 3 O-
10.4
10.5
CH 3 O-
10.6
HO H
PBr3
10.7 How are compounds 10.2 and 10.4 related?
10.8 How are compounds 10.2 and 10.6 related?
11) Draw the products of each reaction.
O
11.1
11.2
H3 C
H 3C
CH 3CH2 OH
H
H
CH 3
H2 SO4
[1] CH 3CH2 ONa
O
[2] H2 O
O
HBr
11.3
O
11.4
[1] NaCN
[2] H2 O
2302169 Chem Med Studt
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12) Draw the products of each reaction, and indicate the stereochemistry when appropriate.
OTs
12.1
KOC(CH 3 )3
OH
12.2
H
HBr
CH 3
O
12.3 CH 3CH2
H
[1] NaCN
H
CH 2CH3
[2] H 2O
OTs
12.4 (H C) C
3 3
KCN
H
PBr3
OH
12.5
H3 C
OH
12.6
[2] CH3 CH 2O -
H D
12.7
O
[1] TsCl, pyridine
HBr
[1] NaOCH3
12.8
O
[2] H 2O
OH
12.9
CH 2 CH 3
CH3
12.10 H 3CH2 C C OCH 3
CH3
[1] NaH
[2] CH3 CH2 I
HI