Concept explainers
For each compound drawn below:
a. Label each
b. Classify each conformation as cis or trans.
c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.
d. Draw the second possible chair condformation for each compound.
[1] [b] [c]
Want to see the full answer?
Check out a sample textbook solutionChapter 4 Solutions
Organic Chemistry (6th Edition)
Additional Science Textbook Solutions
Chemistry: A Molecular Approach (4th Edition)
Introductory Chemistry (5th Edition) (Standalone Book)
Organic Chemistry As a Second Language: Second Semester Topics
Thermodynamics, Statistical Thermodynamics, & Kinetics
Organic Chemistry
Organic Chemistry - Standalone book
- 1. Consider the structure below and draw its most stable and least stable conformations in Newman Projections while looking down the bond indicated. W a. The lowest energy (most stable) conformation is staggered b. The highest energy (least energy) conformation is eclipsedarrow_forward1) Use conformations A andB shown below to answer the following questions. Br. H Br H H H H H CI Conformation A Conformation B Newman projection conformation A a) In the space to the right above, draw a Newman projection looking down the carbon-carbon bond of conformation A. Part of the Newman projection has been drawn for you. b) Which conformation would be more stable (A or B)? c) Which conformation has greater steric strain? (A or B)? d) Circle all the terms that accurately describe conformation A. STAGGERED ECLIPSED GAUCHE ANTI e) Circle all the terms that accurately describe conformation B. STAGGERED ECLIPSED GAUCHE ΑΝΤΙarrow_forward4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: higher energy conformation: á most stable conformation: higher energy conformation: 3 Daarrow_forward
- 3. Consider the structure below and draw its most stable and least stable conformations in Newman Projections while looking down the bond indicated پر a. The lowest energy (most stable) conformation is Anti. b. The highest energy (least stable) conformation is eclipsed.arrow_forward4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: # higher energy conformation: most stable conformation: higher energy conformation: 00 Do poarrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a.Label the substituents on C1, C2, and C4 as axial or equatorial. b. Are the substituents on C1 and C2 cis or trans to each other? c.Are the substituents on C2 and C4 cis or trans to each other? d.Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward
- 3. Answer the following parts (a-c) based on the Newman projection shown H3CH a. Draw the exact conformation of the molecule that is represented by the Newman projection in a structural, wedge-dash formula. CH3 TOH b. Provide the IUPAC name for this compound. c. Fill in the blanks: The dihedral angle between the hydroxyl and the methyl groups in the box with the dotted line is degrees. The relationship between these same two This interaction causes groups can be labeled as strain and results in the destabilization of this conformer compared with other conformers for this molecule. 8:05 PM 75°F 9/21/2021arrow_forward3. For pentane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.arrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a. Label the substituents on C1, C2, and C4 as axial or equatorial.b. Are the substituents on C1 and C2 cis or trans to each other?c. Are the substituents on C2 and C4 cis or trans to each other?d. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward
- a. b. For the following two pairs of molecules, (1) Draw out the chair conformation for each molecule, flip the ring if it is possible. (2) Compare both molecules to circle out which one is more stable. (3) Identify their relationship as: constitutional isomer, conformational isomer, stereoisomer or identical. (4) Find all the chiral center on each molecule and label them. Br and ZX- and VS. H H H Br H H ∞arrow_forwardFor 1,2-dichloroethane: a.Draw Newman projections for all eclipsed conformations formed by rotation from 0° to 360° about the carbon-carbon single bond. b.Which eclipsed conformation(s) has (have) the lowest energy? Which has (have) the highest energy? c.Which, if any, of these eclipsed conformations are related by reflection?arrow_forward3. Draw the most stable chair conformation of (trans) 3-t-butylcyclohexanol. 4. State whether these two are: a) the same molecule b) different compounds that are not isomers c) constitutional isomers d) diastereomers e) enantiomers H CH3 CH₁ Br Br Br CH3 H Br H CH3arrow_forward
- 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