ORGANIC CHEMISTRYPKGDRL+MLCRL MDL
3rd Edition
ISBN: 9781119416746
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 4, Problem 50PP
Interpretation Introduction
Interpretation:
Chair conformations of menthol should be drawn and least energetic conformer is needed to be predicted between them.
Concept introduction:
Chair conformer: chair conformer is a stable conformer for cyclohexane compound. in this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.
Example:
After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.
Stereochemistry conversions in chair conformation are shown below.
Substituent position | cis | trans |
1,2 position | (a,e) or (e,a) | (a,a) or (e,e) |
1,3 position | (a,a) or (e,e) | (a,e) or (e,a) |
1,4 position | (a,e) or (e,a) | (a,a) or (e,e) |
To find: chair conformer of the menthol molecule.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Don't used hand raiting and don't used Ai solution
Don't used hand raiting and don't used Ai solution
Q3: Arrange each group of compounds from fastest SN2 reaction rate to slowest SN2
reaction rate.
CI
Cl
H3C-Cl
CI
a)
A
B
C
D
Br
Br
b)
A
B
C
Br
H3C-Br
D
Chapter 4 Solutions
ORGANIC CHEMISTRYPKGDRL+MLCRL MDL
Ch. 4.2 - Prob. 1LTSCh. 4.2 - Prob. 1PTSCh. 4.2 - Prob. 2PTSCh. 4.2 - Prob. 3ATSCh. 4.2 - Prob. 2LTSCh. 4.2 - Prob. 4PTSCh. 4.2 - Prob. 5ATSCh. 4.2 - Prob. 3LTSCh. 4.2 - Prob. 6PTSCh. 4.2 - Prob. 7ATS
Ch. 4.2 - Prob. 4LTSCh. 4.2 - Prob. 8PTSCh. 4.2 - Prob. 9PTSCh. 4.2 - Prob. 10ATSCh. 4.2 - Prob. 5LTSCh. 4.2 - Prob. 11PTSCh. 4.2 - Prob. 12PTSCh. 4.2 - Prob. 13ATSCh. 4.3 - Prob. 6LTSCh. 4.3 - Prob. 14PTSCh. 4.3 - Prob. 15ATSCh. 4.6 - Prob. 7LTSCh. 4.6 - Prob. 16PTSCh. 4.6 - Prob. 17ATSCh. 4.7 - Prob. 18CCCh. 4.8 - Prob. 8LTSCh. 4.8 - Prob. 19PTSCh. 4.8 - Prob. 20ATSCh. 4.11 - Prob. 9LTSCh. 4.11 - Prob. 21PTSCh. 4.11 - Prob. 22ATSCh. 4.11 - Prob. 10LTSCh. 4.11 - Prob. 23PTSCh. 4.11 - Prob. 24ATSCh. 4.12 - Prob. 11LTSCh. 4.12 - Prob. 25PTSCh. 4.12 - Prob. 26ATSCh. 4.12 - Prob. 27CCCh. 4.13 - Prob. 12LTSCh. 4.13 - Prob. 28PTSCh. 4.13 - Prob. 29ATSCh. 4.13 - Prob. 13LTSCh. 4.13 - Prob. 30PTSCh. 4.13 - Prob. 31ATSCh. 4.13 - Prob. 32ATSCh. 4.14 - Prob. 33CCCh. 4.14 - Prob. 34CCCh. 4.14 - Prob. 35CCCh. 4 - Prob. 36PPCh. 4 - Prob. 37PPCh. 4 - Prob. 38PPCh. 4 - Prob. 39PPCh. 4 - Prob. 40PPCh. 4 - Prob. 41PPCh. 4 - Prob. 42PPCh. 4 - Prob. 43PPCh. 4 - Prob. 44PPCh. 4 - Prob. 45PPCh. 4 - Prob. 46PPCh. 4 - Prob. 47PPCh. 4 - Prob. 48PPCh. 4 - Prob. 49PPCh. 4 - Prob. 50PPCh. 4 - Prob. 51PPCh. 4 - Prob. 52PPCh. 4 - Prob. 53PPCh. 4 - Prob. 54PPCh. 4 - Prob. 55PPCh. 4 - Prob. 56PPCh. 4 - Prob. 57PPCh. 4 - Prob. 58PPCh. 4 - Prob. 59PPCh. 4 - Prob. 60PPCh. 4 - Prob. 61IPCh. 4 - Prob. 62IPCh. 4 - Prob. 64IPCh. 4 - Prob. 65IPCh. 4 - Prob. 66IPCh. 4 - Prob. 67IPCh. 4 - Prob. 68IPCh. 4 - Prob. 69IPCh. 4 - Prob. 70IPCh. 4 -
All of the following are representations of...Ch. 4 - Prob. 72IPCh. 4 -
Which of the following is expected to have the...Ch. 4 - Prob. 74IPCh. 4 - Prob. 75CPCh. 4 -
The all-trans-1,2,3,4,5,6-hexaethylcyclohexane...Ch. 4 -
Compounds 1 and 2 were prepared, and the...
Knowledge Booster
Similar questions
- Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution, respectively. F CI Br | Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to have a reasonable yield of product. NH2 Br Br Br .OH Brarrow_forwardClassify each molecule as optically active or inactive. Determine the configuration at each H соон Chirality center OH 애 He OH H3C Ноос H H COOH A K B.arrow_forwardQ1: Rank the relative nucleophilicity of the following species in ethanol. CH3O¯, CH3OH, CH3COO, CH3COOH, CH3S Q2: Group these solvents into either protic solvents or aprotic solvents. Acetonitrile (CH3CN), H₂O, Acetic acid (CH3COOH), Acetone (CH3COCH3), CH3CH2OH, DMSO (CH3SOCH3), DMF (HCON(CH3)2), CH3OHarrow_forward
- Don't used hand raiting and don't used Ai solutionarrow_forward10. The main product of the following reaction is [1.1:4',1"-terphenyl]-2'-yl(1h-pyrazol-4- yl)methanone Ph N-H Pharrow_forwardDraw the Fischer projection for a D-aldo-pentose. (aldehyde pentose). How many total stereoisomers are there? Name the sugar you drew. Draw the Fischer projection for a L-keto-hexose. (ketone pentose). How many total stereoisomers are there? Draw the enantiomer.arrow_forward
- Draw a structure using wedges and dashes for the following compound: H- Et OH HO- H H- Me OHarrow_forwardWhich of the following molecules are NOT typical carbohydrates? For the molecules that are carbohydrates, label them as an aldose or ketose. HO Он ОН ОН Он ОН но ΤΗ HO ОН HO eve Он он ОН ОН ОН If polyethylene has an average molecular weight of 25,000 g/mol, how many repeat units are present?arrow_forwardDraw the a-anomer cyclized pyranose Haworth projection of the below hexose. Circle the anomeric carbons. Number the carbons on the Fischer and Haworth projections. Assign R and S for each chiral center. HO CHO -H HO -H H- -OH H -OH CH₂OH Draw the ẞ-anomer cyclized furanose Haworth projection for the below hexose. Circle the anomeric carbons. Number the carbons on the Fischer and Haworth projections. HO CHO -H H -OH HO -H H -OH CH₂OHarrow_forward
- Name the below disaccharide. Circle any hemiacetals. Identify the numbering of glycosidic linkage, and identify it as a or ẞ. OH HO HO OH HO HO HO OHarrow_forwardWhat are the monomers used to make the following polymers? F. а. b. с. d. Вецер хочому なarrow_forward1. Propose a reasonable mechanism for the following transformation. I'm looking for curved mechanistic arrows and appropriate formal charges on intermediates. OMe MeO OMe Me2N NMe2 OTBS OH xylenes OMe 'OTBSarrow_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