Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3.15, Problem 3.27P
- a. Draw both chair conformations of cis-1 4-dimethylcyclohexane and determine which conformer is more stable.
- b. Repeat for the trans isomer.
- c. Predict which isomer (cis or trans) is more stable.
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Take a look at the butane conformers below.
Identify:
(a)Which is an anti conformation in Newman?
(b)Which is a Gauche conformation?
(c)Which is the more stable Sawhorse conformer?
(d)Which has the same potential energy/strain with ALS?
Draw both cis chair conformations of 2-methylcyclohexanol and circle the more stable one.
Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
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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
- 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.arrow_forwardFollowing 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?arrow_forwardConsider 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?arrow_forward
- Indicate the relationship between each pair. Choose from: configurational stereoisomers,conformers, constitutional isomers, or different formulas (Each term is used at least twice.)arrow_forwardFill 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.arrow_forwardDraw the two chair conformations of trans-1-chloro-2-methylcyclohexane. Which is more stable?arrow_forward
- Draw both trans chair conformations of 2-methylcyclohexanol and circle the more stable one.arrow_forwardAre my chair conformations correct? What about the energies of each conformation according to the table?arrow_forwarda) i) Draw the Newman projections for the conformations of ethane (staggered and eclipsed) 2. Which is higher in energy? Which is more stable? 3. Next to each conformer, draw the equivalent ‘sideways’ view, using wedged bondsarrow_forward
- Which chair conformation is more stable? Is it the right because bromine has a larger mass than a methyl group? Or is it the left because the methyl group has three hydrogens stemming from the carbon and is therefore ‘bulkier?’arrow_forwardWhich stereoisomer has the lower overall energy? Draw the chair for the lowest energy conformation.arrow_forwardDraw both a chair confirmation of the substitutes cyclohexane drawn below. Be certain to actually do a ring flip. Also be certain to very clearly distinguish axial from equatorial positions. Then circle the more stable conformation.arrow_forward
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