needed for this question. a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below. b. Specify substituent positions (axial or equatorial) in the more stable chair. c. Estimate the percent of the more stable chair at equilibrium at 25°C. (To determine the percent of the more stable chair at equilibrium, first calculate Keor and then use this value to find the percentage.) H3C OH (in isopropanol) Answers: a. The energy difference is b. In the more stable chair: kJ/mol. o The methyl group is in the o The hydroxyl group is in the 8 position. 8 position. c. At 25°C the equilibrium percent of the more stable chair conformation is approximately

needed for this question. a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below. b. Specify substituent positions (axial or equatorial) in the more stable chair. c. Estimate the percent of the more stable chair at equilibrium at 25°C. (To determine the percent of the more stable chair at equilibrium, first calculate Keor and then use this value to find the percentage.) H3C OH (in isopropanol) Answers: a. The energy difference is b. In the more stable chair: kJ/mol. o The methyl group is in the o The hydroxyl group is in the 8 position. 8 position. c. At 25°C the equilibrium percent of the more stable chair conformation is approximately

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 10CTQ: Consider the Newman projection below. a. Draw a full Lewis structure of this molecule with...

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Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.
Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.
Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.
Consider the Newman projection below. a. Draw a full Lewis structure of this molecule with R1=Me,R2=Et , and R3=iPr . b. Given the sizes of these R groups (R3R2R1) , does the Newman projection above show thelowest potential energy conformation of this bond? If not, draw a Newman projectionshowing the lowest P.E. conformation (sighting down this same bond). c. To draw a Newman projection in the lowest P.E. conformation, the following rule of thumbusually applies: Place the largest group on the front carbon anti to the largest group on theback carbon. Is your answer to the previous question consistent with this rule of thumb?
Draw the Newmann projections of this molecule along the circled bond of this molecule, from the point of view of the eye. You should include and label the syn-periplanar, gauche, anticlinal and anti-periplanar conformations, and whether the conformation is staggered or eclipsed. List these four conformations from most stable to least stable?
For every structure below, draw the most stable chair conformation. Where two or more conformations are equally stable, draw both.
Starting from the Newman projection below, rotate the back carbon to provide the structure in a gauge staggered conformation.
Consider the substituted cyclohexane shown in the ball-and-stick model. (See attached) Draw the second possible conformation in the chair form, and classifyit as more stable or less stable than the conformation shown in thethree-dimensional model ?
Calculate strain energy for the conformed pictured below, using strain energy increments from the table.
I still don't know in which direction (axial or equatorial) the hydrogens are in both chair conformations of MCHM. Can you please draw the two conformations including the hydrogens?
Observe the Newman projection of the next molecule along the bond shown in red with the front carbon the one bonded to "Cl". a) Draw one of the Newman projections of the molecule with a staggered conformation. b) Draw one of the Newman projections of the molecule with an eclipsed conformation.