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, Problem 46P
(a)
Interpretation Introduction
Interpretation : The structure of (R)-3-bromo3-methylhexane needs to be drawn.
Concept Introduction : The R and S configuration is decided by the direction of rotation of the molecule about a plane.
(b)
Interpretation Introduction
Interpretation : The structure of 3, 5-dimethylheptane molecule needs to be drawn.
Concept Introduction : The configuration shows in chiral atom. When four different groups attached to the single atom that atom is called chiral atom.
(c)
Interpretation Introduction
Interpretation : The structure of 2-bromo,3-methylpentane needs to be determined.
Concept Introduction : If the 4th priority group is below the plane and rotates clockwise then that molecule has R configuration in it.
(d)
Interpretation Introduction
Interpretation : The structure of 1,1,2-trimethylcyclopropane needs to be drawn.
Concept Introduction : The configuration of molecule decided by the direction of the rotation of the chiral atom about the plane axis.
(e)
Interpretation Introduction
Interpretation : The structure of 1-choloro, 1-trifloromethyl-2-methylcyclobutane and 1,2-dichloro,3-ethylcycclohexane needs to be drawn.
Concept Introduction : The configuration of the molecule follows the Cahn-Ingold-Prelog priority rules. Clockwise rotation represents the R configuration and anticlockwise shows the S configuration.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Draw a three-dimensional structure for each compound, and star all asymmetric carbon
atoms. Draw the mirror image for each structure, and state whether you have drawn a
pair of enantiomers or just the same molecule twice. Build molecular models of any of
these examples that seem difficult to you.
(a)
ОН
(b)
(c)
NH,
ОН
СH—CH—СООН
|
pentan-2-ol
pentan-3-ol
alanine
(d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane
(h)
(i)
H
CH;
"H
H.
H
CH,
H
Q1: Draw the structure of each of the following molecules:
(a) (R)-1-chloro-1-fluorobutane
(c) (2R,35)-3-Bromo-2-chloro-1-pentanol
(4
(b) (S)-2-chloropentane;
(d) (R)-2,2,3-trichlorobutane.
utures Fxamples are
(−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.
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
- 12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forward(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.arrow_forwardDraw a line structure for (4E,7S)-7-benzyl-5-fluoronon-4-en-2-one with threedimensional information where appropriate. Place the ketone group on the right-hand side of your drawing.arrow_forward
- For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning. (a) (CH3)3C-C(CH3)3 or (CH3),CH-CH2CH,-CH(CH3)2 (b) CH3(CH2),CH3 or CH3(CH2)5CH2OH (c) CH3CH20CH,CH3 or CH3CH,CH,CH2OHarrow_forward(a) Draw a three-dimensional line structure of (5R,6Z)-6,7-dichloro-5-hydroxynon-6-enal. Place the aldehyde group on the right-hand side of your drawing.(b) Give the Cahn-Ingold-Prelog priority order of the four groups (-OH, -H, -(CH2)3CHO, -C4H5Cl2) at the C5 stereocentre (Highest 1 > 2 > 3 > 4 Lowest).arrow_forward(a) (R)-1,1,2-trimethylcyclohexane, label each structure you have drawn as chiral or achiral.arrow_forward
- Draw the structure of the following three isomeric esters with chemical formula C-H1,0,. Ester #1: (E)-ethyl 2-pentenoate Ester #2: ethyl 3-methyl-3-butenoate Ester #3: (Z)-methyl 3-hexenoate • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. opy aste ChemDoodle Previous Next Email Instructor Save and Exitarrow_forward6. Which of the following substances have meso forms? Draw them. (a) 2,3-Dibromobutane (b) 2,3-Dibromopentane (c) 2,4-Dibromopentane 7. What kinds of isomers are the following pairs? (a) (S)-5-Chlorohex-2-ene and chlorocyclohexane (b) (2R,3R)-Dibromopentane and (2S,3R)-dibromopentanearrow_forwardDraw the structure of each molecule. (a) (S)-1-chloro-2,2-dimethyl-1-phenylcyclopentane; (b) (1R,2S)-1-methyl-1,2-dinitrocyclopropane; (c) (R)-4-ethoxycyclohexene; (d) (3S,4S)-3-chloro-4-fluoro-2-methylhepta-1,6-dienearrow_forward
- 1. Determine whether the molecule is chiral or achiral OH CH2OH CH3 OH HO2CC. CO2H Full-screen Snip OH A. В. 2. Oseltamivir phosphate (sold under the trade name Tamiflu) is a prescription antiviral drug that is used in the treatment of both Influenza virus type A and Influenza virus type B. Identify all the stereocenters by labelling with an asterisk (*). H NH3+ HPO4- Oseltamivir phosphate (Tamiflu)arrow_forward2) Draw Newman projections of all staggered conformations of (S)-butan-2-ol. Clearly mark the highest energy conformation. 3) Draw both chair conformations of (1S,3R)-1-chloro-3-isopropylcyclohexane. Clearly mark the most stable conformation, and also the conformation which enables E2 elimination.arrow_forwarda) Considering compounds 2a through 21, identify: ONE PAIR of geometric isomers; TWO PAIRS of enantiomers and THREE PAIRS of identical molecules. b) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers. Draw the relevant structures in the space provided in the Answer Booklet. c) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify your ordering. 2 НО. AH H H anulta HOwno barwolset of ef 28nuor OH 2bc 2c ning) bi 10291 H WH 2 st brbot di OH Lacenoqoid OH to nabio ni one nt at dit st 2e OH "H OH bre 2a 2d 2g 2j H HO 2h 2k HO ...H di al nt o 2f 2i 21arrow_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 Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles 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 Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary 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