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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 21E

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Question

Q1: Draw the most stable and the least stable Newman projections about the C2-C3 bond for
each of the following isomers (A-C). Are the barriers to rotation identical for enantiomers A and
B? How about the diastereomers (A versus C or B versus C)?
enantiomers
H_ Br
(S) CH 3
H3C (S)
H Br
A
H Br
省
H3C (S) (R) CH₂
Br H
C
H Br
H3C (R)
B
(R)CH3
H Br
H Br
H3C (R)
(S) CH3
Br H
D
identical

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Q1: Draw the most stable and the least stable Newman projections about the C2-C3 bond for each of the following isomers (A-C). Are the barriers to rotation identical for enantiomers A and B? How about the diastereomers (A versus C or B versus C)? H Br H Br (S) CH3 (R) CH3 H3C (S) H3C H Br Br H A C enantiomers H Br H Br (R) CH3 H3C (R) (S) CH3 H3C H Br Br H B D identical
Q1: Draw the most stable and the least stable Newman projections about the C2-C3 bond for each of the following isomers (A-C). Are the barriers to rotation identical for enantiomers A and B? How about the diastereomers (A versus C or B versus C)? enantiomers H Br H Br (S) CH3 H3C (S) (R) CH3 H3C H Br A Br H C H Br H3C (R) B (R)CH3 H Br H Br H3C (R) (S) CH3 Br H D identical
Draw (15,25,3R)-1-bromo-3-chloro-2-fluorocyclohexane (shown below) in both its chair forms! Draw the Newman projection of the most stable conformation of (15,25,3R)-1-bromo- 3-chloro-2-fluorocyclohexane through carbons 1 and 2 and carbons 2 and 3. مه c
What are the relative energy levels of the three staggered conformations of 2,3-dimethylbutane when looking down the C2-C3 bond? Me Me H Me Me Me Me Me. Me Conformation: 191 1ක් පුදා H Me Me Me H H H A B C Me A is the highest energy conformation and C is the lowest (energy level of B is in between the two) O A and B are equal energy, and C is the highest energy conformation A and B are equal energy, and C is the lowest energy conformation C is the highest energy conformation and A is the lowest (energy level of B is in between the two) O B is the highest energy conformation and C is the lowest (energy level of A is in between the two)
5-54 Ribose, an essential part of ribonucleic acid (RNA), has the following structure: H H H OH CHO Ribose Но но н но н (a) How many chirality centers does ribose have? Identify them. (b) How many stereoisomers of ribose are there? (c) Draw the structure of the enantiomer of ribose. (d) Draw the structure of a diastereomer of ribose.
4
Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each asymmetric carbon in chloramphenicol? HỌ H c-c-CH,OH NHCCHCI, NO2 chloramphenicol
Draw the Newman projections of the most stable and least stable conformations of 2, 3, 3-trimethylpentane, viewed down the bond from C to C. Part 1 of 2 Draw the most stable conformation. Part 2 of 2 Draw the least stable conformation, by o pa 3 C Draw the Newman projections of the most stable and least stable confermations of 2,3,3-trimethy pentane, viewed down the bond from C, to C Part 1 of 2 Draw the most stable conformation ** Part 2 of 2 Draw the least stable conformation. ** & X X 3 Ć Č 2 DJ
2. From the molecules below, determine the relationship between each pair (a-b, a-c, a-d, etc.): identical, constitutional isomers, enantiomers, diastereomers. In this problem, conformational isomers are considered identical, PUCH H HOCH an e OF CH 學 HOCH。 HOCH CH H OH 10- h H d. E HO CH "OH CH₂CH PHON 美 FOH H -OH
Following is a staggered conformation for one of the enantiomers of 2-butanol Q. viewed along the bond between carbons 2 and 3, draw a Newman projection for this staggered conformation.
Complete the Newman projection below to draw the most stable conformation of 3-methylpentane, looking down the C2-C3 bond. Identify each substituent using "H" for hydrogen and "Me" for methyl. a= b= c= d=
2. Assign E or Z configuration to each of the following alkenes: (b) HO2C (a) HOCH2 CH3 C=C CI OCH3 H3C CH3 {d} CH3O2C CH=CH2 (c) NC C=C HO2C CH2CH3 CH3CH2 CH2OH

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