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
Concept explainers
Question
Chapter 5.3, Problem 5.12E
Interpretation Introduction
Interpretation: The structure of enantiomer of given compounds needs to be drawn and their configuration needs to be determined.
Concept Introduction: Enantiomers are those compounds which have same molecular formula, but the arrangements of groups are different from each other.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
) Draw trans-1-chloro-3-ethylcyclohexane in the box below and assign the stereocenters
doesn't matter which enantiomer you draw). Then draw any diastereomer , any chiral
constitutional isomer (+1 XC draw any one achiral constitutional isomer)
C, = R or S
C, =Ror S
trans-1-chloro-3-ethylcyclohexane
Any diastereomer
CHIRAL constit. isome
ACHIRAL constit. isomer
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
For the following molecules, draw all possible stereoisomers using line-angle formulas with
wedge/dash notation. Label the stereocenters as R or S. Indicate which ones are enantiomers
and which ones are diastereomers. (Remember: there are 2 stereoisomers possible for a
molecule with n chiral centers)
(A)
(B)
(C)
(1 chiral center)
Br
OH
(2 chiral centers)
CI OH
CH3
(3 chiral centers)
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
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
- 2. The following molecule is one enantiomer of methylenedioxymethamphetamine (MDMA). 2a. Circle all of the stereocenters in MDMA 2b. Assign the absolute stereochemistry (R or S) for each stereocenter .CH3 HN H H *CH3arrow_forward3) a) Using Newman projections, draw the lowest and highest energy conformers of 2- methylbutane, with respect to rotation around the C2-C3 bond. b) What is the barrier to rotation (difference in energy between lowest and highest) around the C2-C3 bond of 2-methylbutane?arrow_forwardPredict the expected major product(s) of the following reaction sequence. ی ہیں میں قبر ہیں H 1. t-BuOK, t-BuOH 2. O3, CH2Cl2, -78 °C 3. MezS H OH OH + enantiomer Harrow_forward
- 1,2-bis(methylthio)cyclohexane has two asymmetric carbons, thus 4 possible stereoisomers. However, one stereoisomer is a meso compound, so there are only 3. a) Draw all possible stereoisomers. Change the given structures by adding dashes and wedges. Draw the correct stereoisomer of each configuration above the provided labels. i.e draw the (R, S) configuration above the label (R, S). b) Label the enantiomers, diastereomers, and meso compound by filling in the chart (If you redraw the molecules, keep in the same order with the amine groups on the right side of the molecule!) Change the squiggly lines to dashed or wedges in the given structures to make 3 stereoisomers NH₂ NH₂ cyclopentane-1,2-diamine Enantiomers are structures Diastereomers are structures The meso compound is structure NH₂ C 1 (R, S) NH₂ NH Structure(s) 2 (S, S) 2 "NH₂ NH 2 NH 2 3 (R, R)arrow_forwardIdentify 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.arrow_forwardg) Reaction 1g pts] For 2-chloro-3-fluorocyclohexane, draw all possible stereoisomers, and identify their stereochemical relationships using the labels we used in class (E = enantiomers; D=Diastereomers; I = identical.) Make sure to label each chiral carbon in each compound with the correct R/S designation.arrow_forward
- 8. 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_forwardI was wondering if theres an error in the answer booklet. Because we have a double bond so I thought it was E and 3S because of the stereocenter?arrow_forwardConsider this molecule, which contains one chirality center. What is the highest-priority substituent at this chirality center? () -CH,CH, -CH, -Br What is the lowest-priority substituent at this chirality center? -CH, -CH₂CH₂ Name the structure. (S)-2-bromobutane (R)-2-bromobutane 0 FOREX OH zoom in Br Qarrow_forward
- (a) (d) 5. Assign the R and S configurations for all stereogenic centers in the following compounds. BI H CH(CH₂)₂ KAMION WOH H₂C H CH₂ Br -H Br +H CH, (0) CH=CH₂ H+C₂0 -C=CCH₂ CH₂CH₂CH₂C1 CH₂CH₂CI H₂NH CH₂CH₂Cl CH₂CH₂CH₂OH H₂N CH₂CH₂OH CH₂arrow_forwardDetermine the absolute Configuration (2 ors) of the Stereogenic centre in (i) and (ii) HO # CH ₂ Br (ii) HO compounds CHO H 1 CH₂2₂ CH ₂arrow_forwardA sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S -adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
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