7. For the following molecules, circle all that are chiral. OH Br 5 i H₂N COOH Dun ||

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
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Chapter12: Chirality
Section: Chapter Questions
Problem 19E
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7. For the following molecules, circle all that are chiral.
OH
Br
5
h
H₂N
COOH
8. Identify each pair of molecules below as ENANTIOMERS or DIASTEREOMERS or THE SAME MOLECULE. For this
question, those are the only three options. Please write your answer within the dotted lines for each set.
CH3
CH3
Bru
H
CH₂CH3
H
Br
(3S,4R,5S)-5-iodo-3,4-dimethyldecane
(3R,4S,5R)-5-iodo-3,4-dimethyldecane
Br.
Br
CH₂CH3
Br
Br
Bri
F
9. The specific rotation of D-3-methylshamrockomycin is +32.40°. Determine the ee of a
mixture of D- and L-3-methylshamrockomycin if the specific rotation of the mixture is +9.72.
Please write your answer in the box to the right:
H
F
Which enantiomer is favored? Shade the circle (O) that corresponds to your answer.
O(S)-3-methylshamrockomycin O(R)-3-methylshamrockomycin
HO
Br
H
Br
10. Identify the isomeric relationship between each pair of molecules below. The options are:
ENANTIOMERS
CONSTITUTIONAL ISOMERS
DIASTEREOMERS
SAME MOLECULE
Please write your answer within the dotted lines for each set!
CH3
CH₂CH3
CI
CI
JMC
H
CH₂CH3 Br CH3
Br
CI How
HO
Br
f
CI
CI
Win
Br
H
H
O not enough info to answer
NOT ISOMERS
(3S,4R,5S)-trimethylnonane
(3R,4S,5S)-trimethylnonane
(3S,4R,5S)-trimethylnonane
(3S,4R,6S)-trimethylnonane
(3S,4R,5S)-trimethyloctane
(3S,4R,5S)-trimethylnonane
11. For the radical halogenation of (R)-3-methylhexane that we studied in Chapter 4,
are the major products chiral?
YES or
NO
will the resulting product solution be optically active? YES or
NO
Hint: it may help to draw out and consider the geometry & stereochemistry of the carbon-based radical intermediate
Transcribed Image Text:7. For the following molecules, circle all that are chiral. OH Br 5 h H₂N COOH 8. Identify each pair of molecules below as ENANTIOMERS or DIASTEREOMERS or THE SAME MOLECULE. For this question, those are the only three options. Please write your answer within the dotted lines for each set. CH3 CH3 Bru H CH₂CH3 H Br (3S,4R,5S)-5-iodo-3,4-dimethyldecane (3R,4S,5R)-5-iodo-3,4-dimethyldecane Br. Br CH₂CH3 Br Br Bri F 9. The specific rotation of D-3-methylshamrockomycin is +32.40°. Determine the ee of a mixture of D- and L-3-methylshamrockomycin if the specific rotation of the mixture is +9.72. Please write your answer in the box to the right: H F Which enantiomer is favored? Shade the circle (O) that corresponds to your answer. O(S)-3-methylshamrockomycin O(R)-3-methylshamrockomycin HO Br H Br 10. Identify the isomeric relationship between each pair of molecules below. The options are: ENANTIOMERS CONSTITUTIONAL ISOMERS DIASTEREOMERS SAME MOLECULE Please write your answer within the dotted lines for each set! CH3 CH₂CH3 CI CI JMC H CH₂CH3 Br CH3 Br CI How HO Br f CI CI Win Br H H O not enough info to answer NOT ISOMERS (3S,4R,5S)-trimethylnonane (3R,4S,5S)-trimethylnonane (3S,4R,5S)-trimethylnonane (3S,4R,6S)-trimethylnonane (3S,4R,5S)-trimethyloctane (3S,4R,5S)-trimethylnonane 11. For the radical halogenation of (R)-3-methylhexane that we studied in Chapter 4, are the major products chiral? YES or NO will the resulting product solution be optically active? YES or NO Hint: it may help to draw out and consider the geometry & stereochemistry of the carbon-based radical intermediate
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