Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Question
Chapter 5, Problem 42P
Interpretation Introduction
Interpretation : The R configuration of the enantiomers needs to be determined.
Concept Introduction : The name of R and S configuration is decided by the fourth priority group. When fourth priority group is below the chiral atom and going clockwise then its R otherwise S. When fourth priority group is above the chiral atom and goes anticlockwise then its R otherwise S.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Identify the stereogenic carbon in (S)- and (R)-limonene, rank the substituents around it and rationalize the assignment of their stereochemical configurations. Hint: When ranking carbons that have multiple bonds, consider the bolded carbon of C=C being connected to 2 carbons and the bolded carbon of C≡C being connected to 3 carbons.
8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below.
(a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle.
(b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle.
(a)
НО.
Carbon a
HO
O OH
Carbon a:
OR
OS
Carbon b
H
N
Carbon b:
R
OS
of
H
Carbon c:
OR
OS
OH OH
Carbon c
F
Carbon d:
R
OS
OH
Carbon d
(b) The two
structures are:
O the same
compound
O stereoisomers
Determine whether each of the following names describes a single stereoisomer unambiguously. For each one that does,rewrite the name using the R and S designations for the chiral centers if appropriate. (a) cis-1,2-difluorocyclohexane;(b) trans-1,2-difluorocyclohexane; (c) trans-1,4-difluorocyclohexane; (d) cis-1-chloro-2-fluorocyclohexane;
(e) trans-1,4-dimethylcycloheptane
Chapter 5 Solutions
Organic Chemistry: Structure and Function
Ch. 5.1 - Prob. 5.3ECh. 5.1 - Prob. 5.4ECh. 5.1 - Prob. 5.5ECh. 5.2 - Prob. 5.6ECh. 5.2 - Prob. 5.8TIYCh. 5.3 - Prob. 5.9ECh. 5.3 - Prob. 5.11TIYCh. 5.3 - Prob. 5.12ECh. 5.4 - Prob. 5.13ECh. 5.4 - Prob. 5.14E
Ch. 5.4 - Prob. 5.16TIYCh. 5.4 - Prob. 5.17ECh. 5.5 - Prob. 5.18ECh. 5.5 - Prob. 5.19ECh. 5.5 - Prob. 5.20ECh. 5.6 - Prob. 5.21ECh. 5.6 - Prob. 5.22ECh. 5.6 - Prob. 5.23ECh. 5.7 - Prob. 5.24ECh. 5.7 - Prob. 5.26TIYCh. 5.7 - Prob. 5.27ECh. 5 - Prob. 5.1ECh. 5 - Prob. 5.2ECh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - Prob. 50PCh. 5 - Prob. 51PCh. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Prob. 58PCh. 5 - Prob. 59PCh. 5 - Prob. 60PCh. 5 - Prob. 61PCh. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Prob. 64PCh. 5 - Prob. 65PCh. 5 - Prob. 66PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 - Prob. 70PCh. 5 - Prob. 71P
Knowledge Booster
Similar questions
- 2. Label any stereocenters in the following molecule as (R) or (S): ОН H. .CH3 `CH3 ОНarrow_forward3 Which is the stereochemical relationship between this pair of molecules?arrow_forward1. Draw all of the stereoisomers of 2,4-dichloropentane. Indicate the relationship between these stereoisomers, such as enantiomers, diastereomers, or meso compounds.arrow_forward
- 2. Assign the stereochemical configuration of the selected carbon-carbon double bonds (E, Z or N (not a stereocenter)) that are indicated by the arrows. a) HN H,, H3CO HO H Harrow_forwardDraw all of the possible stereoisomers of the compound shown. Group them as enantiomeric pairs, or indicate any meso compounds. Label all stereocenters with the absolute stereochemistry (R or S).arrow_forward8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)arrow_forward
- [Review Topics) References] M Identify the absolute configuration of the chirality centers in each of the following compounds as R or S. Note: if multiple chirality centers are present, indicate the stereochemical designations as: RR, SS, RS, or SR (Other terms used for chirality center include chiral center, stereocenter, and stereogenic center.) M MD M CH3 req N. req NH2 req HO2C НО-С 9 more group attempts remaining Retry Entire Group Submit Answer Nes Previous Save and Exit 7:01 PM ) E 10/30/2019arrow_forwardThe molecule (I) and (II) are || CH3 **H I Identical Enantiomers Diastereomers Constitutional Isomers Next H3C X IIarrow_forward5. How many stereocenters does this compound have? How many stereoisomers are possible for this compoundarrow_forward
- How many possible stereoisomers can there be for this molecule? Но lanosterolarrow_forward9. Which compound reacts with both NaBH and H/Pt to produce the same product? A) 1 4 2 B) II III CHO ||| D) None of these 10. Reduction of a carbonyl to produce a stereogenic center A) occurs with the formation of both diastereomers. B) occurs with the formation of both enantiomers. (C) occurs stereospecifically yielding a single isomeric product. D) none of these. MgBr 11. Which reagent would you use to produce (S)-1-phenylethanol from phenyl methyl ketone (acetophenone)? 12. A) S-CBS reagent B) R-CBS reagent C) NaBH +S-CBS reagent 4 D) NaBH + R-CBS reagent 4 An aldehyde can be produced by the reaction of the compound shown with which reagent? A) B) || D IV OCH3 I) H₁/Pt III) LiAlH4 II) NaBH4 IV) DIBAL-H 13. LiAlH reacts with which of the following? 4 A) | H .0 CI 0 EtO. 0 B) C) III D) All of these I II IIIarrow_forwardThere are several rings in this structure. As highlighted in the middle diagram, the two explicit H are both attached to a six-membered ring. As highlighted in the right-hand diagram, the two explicit H are both attached to a five- membered ring. What are the stereochemical relationships of these two H to each other with respect to these two rings (cis or trans)? Ph Ph H Ph Ph Ph Ph H Ph Ph Ph Ph H Ph Pharrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY