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1. Draw the structural formula and give the IUPAC name for the following compounds:
a) cis-CH3CH2CH = CHCH2CH3
b) trans-(CH3)2CHCH=CHCH(CH3)2
c) (R)-2-chlorobutane
d) (S)-3-chloro-1-pentene
e) (Z)-2-bromo-2-pentene
f) (3Z,6E)-1,3,6,-octatriene
g) (2R,3R)-2,3-hexanediol
2. Give the complete name of the compounds below including their stereochemistry:
OH
CH3 O
Cl CH3
i. CH3CH2CHCH2-C-OCH2CH3 ii.
CH(CH 3)2
CH(CH 3)2
H3C H
iii.
iv. (H 3C) 2HC
H CH3
HO
H
OH
CH3 O
Cl CH3
i. CH3CH2CHCH2-C-OCH2CH3 ii.
CH(CH 3)2
CH(CH 3)2
H3C H
iii.
iv. (H 3C)2HC
H CH3
HO
H
4. Consider the molecule, 3-chloropropanoic acid. Draw the 3 staggered and 3 eclipsed
conformers for the 360o rotation around the C2-C3 bond.
a) CH3- , CH3CH2-
b) (CH3)3C- , (CH3)2CH-
c) (CH3)2CH , CH2=CH-
d) - CH(OH)CH3 , -OH, - COOH, -CH2OH
e) - CH2NH2, -NO2, -CN, -NH2
1
6. Draw and determine the R and S configuration of pairs of enantiomers (if any) for
the following compounds:
a) 3-Bromohexane d) 3-Chloro-3-methylpentane
b) 1,2-Dibromo-2-methylbutane e) 1,3-Dichloropentane
c) 3-Methyl-3-pentanol f) 3-Methylhexanoic acid
H CH2OH Cl H
H CH3
a C
c
C C
H3C OH
HOH2C OH
Br
H3C
b
C
HOH2C H
CHO CH3
a b
H c
CN C
H COOH
H Cl Br
CH2Br
OH
d
C
H3C COOH
H
2
9. Label all chiral carbons (if any) in the following molecules:
O CH3
a. b. c. d. O
OH Cl
Cl
e. (CH3)2CHCHBrCH3 f. CH3CH2CH2CHOH(CH3)
g. H2NCH(CH3)COOH h. CH3CHBrCHBrCH3
i. CH3CH2CH2CH(CH3)2 j. CH2=CHCHBrCH3
10. Draw and determine the R and S configuration of pair of enantiomers (if any)
from the following compounds:
a) 3-Bromohexane b) 3-Chloro-3-methyl-pentane
c) 1,2-Dibromo-2-methylbutane d) 1,3-Dichloropentane
e) 3-Methyl-3-pentanol f) 3-Methylhaxanoic acid
HO H
Br Cl H
CH2OH H CH3 OH
a. H b. H3C c. d. HOH2C CH3
H3C OH HOH2C H HOH2C H
OH
12. Draw all the possible stereoisomers for the following compounds:
a) 2-Methyl-2,3-pentadiol b) 3,4-Diaminopentanal
c) 3,4-Dichlorohexane d) 4-Methyl-3-hexanol
For every stereoisomers, label all chiral carbons and determine their R or S
configurations. Indicate pairs of enantiomers, diastereomers and meso compounds.
a. Each one of the product was further chlorinated and the number of trichloro
products (C3H5Cl3) from each were determined by gas chromatography. A
gave only one trichloro, B gave two trichloro, C and D each gave three
trichloro products. What are the structures for A, B, C and D?
3
CH3 CH3
COOH NH2
a. H2N H HOOC H H2N COOH
H CH3 H3C COOH NH2 H
H H CH3 OH
b. HO CH2CH3 HO CH3 HO H H3C H
H OH HO H H OH H3CH2C H
H H Br Br
c. H3CH2C Br H CH2CH3 H CH2CH3
H3CH2C Br
Br H H3CH2C H Br H H CH2CH3
CH2CH3 Br CH2CH3 Br
Cl CH2CH3 Cl
H
d. H H CH3
H3CH2C H H H
Cl CH2CH3
Cl CH3 H3CH2C Cl
H CH3 Cl CH3
CH3
Cl H
15. Draw all the possible Fisher projecdtion of 2,3-pentandiol. Label pairs of
enantiomers, diastereomers and meso compounds (if applicable).