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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter12: Chirality

Section: Chapter Questions

Problem 27CTQ

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Related questions

Question

Identify the following pairs of structures as enantiomers, diastereomers, or
identical molecules. Name the chiral centers as R or S.
Et
Et
Br-
HO.
Но-
Br
HO
HO
-Br
-Br
Et
Et
OH
NH2
HO
H.
H-
CI
"Me
Me.
-OH
-NH2
ci
Pr
Pr
H-
Ph
Ph
“NH2
Ph.
Н.
-NH2
-Ph
Pr
Pr
BrH2C
НО
Me.
но
HO,
„Me
HO
Me
Me
“CH2Br
ČHĄBr
ČH;Br
OH
OH
Me
Me
H-
H.
-CH2CI
H-
OH
СООН
ČH2CI

CH3
CH3
HO
-H
H,N-
-H
H-
-F
H-
-F
H-
-NH2
H-
-ОН
ČH3
ČH3
H
H F
H,C
H3C
CH3
CH3
**
Et
Pr
Pr
Me.
Me
*Br
Br
Ét
Et
Br
Br-
Et
`H
-H
-H
Èt
Ét
El
El
Br
Bra
Br
Br
ČH3
ČH3
ČH3

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What is the relationship between these molecules? Enantiomers, Diastereomers, Identicas
Most naturally occurring amino acids have chiral centers (the asymmetric a carbon atoms)that are named (S) by the Cahn–Ingold–Prelog convention (Section 5-3). The commonnaturally occurring form of cysteine has a chiral center that is named (R), however.(a) What is the relationship between (R)-cysteine and (S)-alanine? Do they have the oppositethree-dimensional configuration (as the names might suggest) or the same configuration?(b) (S)-Alanine is an l-amino acid (Figure 24-2). Is (R)-cysteine a d-amino acid or anl-amino acid?
A student decided that the configuration of the asymmetric centers in a sugar such as d-glucose could be determined rapidly by simply assigning the R configuration to an asymmetric center with an OH group on the right and the S configuration to an asymmetric center with an OH group on the left. Is he correct?
Considerthe image below. a. Draw the mirror image of structure I and label it as structure II.b. Are I and II chiral?c. What kind of stereocenters do they represent?
Designate the chiral centers of the following molecules and show which one of them is achiral?
Draw the optical isomers of CH3-CHOH-CHOH-CH3. Indicate the absolute configuration of each chiralcenter. From the drawn isomers, determine which are enantiomers and which are diastereomers, and identify if there are meso compounds. Please draw first the optical isomers before detemining.
Which enantiomer is this molecule? R/R? S/S? R/S? S/R? Give your answer by indicating the configuration of the chiral carbons from left to right on the drawing.
How to determine chirality?
Draw the optical isomers of CH3-CHOH-CHOH-CHO. Indicate the absolute configuration of each chiral center. From the drawn isomers, determine which are enantiomers and which are diastereomers
Write all possible pairs of Enantiomers and Diastereomers from the following molecules.(use numbers(I;II;III;IV) writing pairs). Give explanation.
Identify any chiral centers within the 2 molecules and identify whether each molecule is chiral or archial. If it is chiral, explain whether you expect a single enantiomer or a mixture of enantiomers to be formed.
4. For each of the following structures:a. Identify Chiral Centersb. Identify the chiral carbon configuration as R or Sc. Identify internal symmetry centers if they existd. Identify whether the structure is chiral or achirale. Identify mesostructures from existing

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