Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4, Problem 36P
Interpretation Introduction
Interpretation:
The absolute configuration of
Concept introduction:
The absolute configuration (R/S) at a chiral carbon is determined on the basis of Cahn-Ingold-Prelog (CIP) rules.
If atom/group priorities excluding the lowest priority group follow a clockwise path, the absolute configuration is R. If the path followed is counterclockwise, the absolute configuration is S.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
1. Following are stereorepresentations for the four stereoisomers of
3-chloro-2-butanol.
CH3
CH3
CH3
CH3
H
HÔ► H
HO► H
НО
CI
H.
CI
Hi
Cl
Cl
CH3
CH3
CH3
CH3
(1)
(2)
(3)
(4)
(a) Assign an R or S configuration of each chiral center. Name each
(b) Which compounds are enantiomers?
(c) Which compounds are diastereomers?
(d) Which are meso compounds?
Identify the relationship between the following pair of structures by
describing them as represting enantiomers, diastereomers, constitutional
isomers or two molecules of the same compounds
(a)
(c)
H
H₂C
H
F
Br
Oll
F
CH3
Br
H
and
Br. CH3
H
and
Fumus
(d)
H
H
X-X=-=
CH3
H CH3
(b)
Br
HO
CHO
and
-OH
H
C(O)CH3
and
HO
H-
CHO
-H
-OH
C(O)CH3
b
Threonine is a naturally occurring amino acid used in the production of
proteins in the body. Draw the enantiomer of the molecule shown below. Use
a dash or wedge bond to indicate stereochemistry of substituents on
asymmetric centers, where applicable.
ck
ol
esc
B
1
Q
option
A
2
OH
N
*.
@
NO
2
NH₂
579 124.520
Drawing
W
S
X
H
command
#
3
E
'OH
80
F3
D
$5
4
3
C
a
R
F
de 20
5
V
FS
T
dtv
G
Atoms, Bonds and Rings
HO
6
♫
e
Fo
ONA
Y
B
OH
&
7
H
F7
U
Charges
N
-
8
J
FB
100
1
(
9
M
-00
l
K
H₂N
O
)
-
O
F10
<
L
NH₂
P
Undo
Remove
command
:
D
Chapter 4 Solutions
Organic Chemistry - Standalone book
Ch. 4.2 - Examine the following for chirality centers:Ch. 4.2 - Prob. 2PCh. 4.3 - Prob. 3PCh. 4.3 - Prob. 4PCh. 4.4 - Prob. 5PCh. 4.4 - Prob. 6PCh. 4.5 - Does the molecular model shown represent...Ch. 4.6 - Assign absolute configurations as R or S to each...Ch. 4.6 - Draw three-dimensional representations ofCh. 4.7 - Prob. 10P
Ch. 4.7 - Using the Fischer projection of (R)-2-butanol...Ch. 4.8 - Prob. 12PCh. 4.9 - Prob. 13PCh. 4.9 - Prob. 14PCh. 4.10 - Prob. 15PCh. 4.10 - Draw Fischer projections of the four...Ch. 4.10 - Prob. 17PCh. 4.11 - A meso stereoisomer is possible for one of the...Ch. 4.11 - One of the stereoisomers of...Ch. 4.12 - Prob. 20PCh. 4.12 - Prob. 21PCh. 4.13 - Prob. 22PCh. 4.13 - Prob. 23PCh. 4.13 - Prob. 24PCh. 4.14 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Including stereoisomers, write structural formulas...Ch. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - (-)-Menthol is the most stable stereoisomer of...Ch. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - (a) An aqueous solution containing 10 g of...Ch. 4 - Prob. 44DSPCh. 4 - Prob. 45DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Prob. 48DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Sensipar is a pharmaceutical used for the treatment of hyperparathyroidism in patients with chronic kidney disease. Draw the enantiomer of the molecule shown below. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers, where applicable. ana ab Cock trol esc . Q option A T Z vel @ 2 Drawing 124,528 W S A X H command 3 E 80 F3 D $ 4 C F4 R F 5 V FD T Atoms, Bonds and Rings stv JO G 6 B Y 7 H ⁰0 A F7 U N Charges 8 J ( 9 M FO 1 T K O H F10 L Ⓒ CI Remove P Undo command i { Reset Ⓒ Done + [ ? option 1 1 }arrow_forwardIdentify the relationship between the following pair of structures by describing them as represting enantiomers, diastereomers, constitutional isomers or two molecules of the same compounds (a) (c) H CH3 Br. CH3 Br f-f and Filmas H H CH3 H F Oll H CHO Br X-X ²=-= -OH HO and and H Br H- F C(O)CH, H (b) CH3 (d) H- and HO CHO -H -OH C(O)CH3arrow_forwardConsider (1S,35)-1-(propan-2-yl)-3-methylcyclohexane. Its more stable form is the chair conformer where the substituent is at the axial position. O 3-methyl O 2-propyl O 1-isopropyl none of the other choices show mechanism and tell if addition or susbtitutionarrow_forward
- Which of the following names represent the least stable stereochemical structure for the molecule shown? Br CI O (IR, 2R)-2-bromo-1-chloro-1-cyclopentylhexane O (1S, 2R)-2-bromo-1-chloro-1-cyclopentylhexane O (IR, 2S)-2-bromo-1-chloro-1-cyclopentylhexane O None of thesearrow_forwardFor each pair of compounds, predict the one with a higher boiling point. Which compoundshave zero dipole moments?(a) cis-1,2-dichloroethene or cis-1,2-dibromoethene(b) cis- or trans-2,3-dichlorobut-2-ene(c) cyclohexene or 1,2-dichlorocyclohexenearrow_forwardThe structure of A is shown below. HO 3 -CH2CH=CH2 A (i) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (25, 3R, 5S) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 55) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.arrow_forward
- 3. Assign E or Z stereochemistry to the following alkenes: (a) НОСН2 CH3 (b) HO2C H C=C C=C H3C CI OCH3 (c) NC CH3 (d) CH3O2C CH=CH2 C=C C=C CH3CH2 CH2OH HO2C CH2CH3 4. Classify the following reactions as additions, eliminations, substitutions, or rearrangements: (а) CН3Br + KоН — СH3ОН + KBr (b) CH3CH2C1 + NaOH → (c) H2C=CH2 + H2 H2C=CH2 + NaCl CH3CH3 5. Which of the following are most likely to behave as electrophiles, and which as nucleophiles? Explain. (a) NH4+ (b) C=N- (c) Br+ (d) CH3NΗ, (е) Н—С—С-—нarrow_forwardDraw both cis- and trans-1,4-dimethylcyclohexane in their more stable chair conformations. 5-72 (a) How many stereoisomers are there of cis-1,4-dimethylcyclohexane, and how many of trans-1,4-dimethylcyclohexane? (b) Are any of the structures chiral? (c) What are the stereochemical relationships among the various stereoisomers of 1,4-dimethylcyclohexane?arrow_forwardConsider the reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. -SH C NaOH Draw only the organic product. Select /// Draw Rings More C H S Erase:arrow_forward
- Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forwardAssign priorities to the groups in each set. (a) -CH2OH and -CH2CH2OH (b) -CH2OH and -CH=CH, (c) -CH2OH and -C(CH3)3arrow_forwardFollowing are the alternative chair conformations for trans-2-methylcyclohexanamine: NH₂ Group C=N Br OH CH3 B Using the data for AG for monosubstituted cyclohexanes at room temperature (25°C) and the representative value for the gauche interaction of two equatorially positioned substituents in the 1,2-position: CH3 Submit Answer -NH₂ AG (kJ/mol) -0.8 -2.4 -3.9 axial → equatorial Group NH₂ CH3 1,2-gauche AG (kJ/mol) -5.9 a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign. b) Given your value in (a), calculate the percent of the chair, indicated as B, presented in an equilibrium mixture of the conformers at 25°C. *The actual value will depend on the substituents. The values of the gas constant and the temperature for 25°C are 8.314 JK 'mol and 298 K respectively. Try Another Version 2 item attempts remaining -7.3 3.8 kJ/mol % Previous Nextarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License