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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 1CTQ

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4) Draw an alkene (minimum of 4 carbons) that is in the E conformation and a different alkene (also 4 carbon minimum)
that is in the Z conformation. Provide an explanation as to what makes it E or Z.

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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.
a) Draw the chair conformations of 1, 4 – ditertbutyl cyclohexane and all of its ring flips.b) Determine the most stable and least stable conformations. Explain your answer.
Complete the following for the compound shown below. a) Draw the line structure using the wedge/dash bond convention to show the correct stereochemistry. b) Draw both chair conformations, and indicate that they are in equilibrium using appropriate arrows. c) Label the most stable structure. d) Label the most structure that is the major conformer in solution. e) Explain your answers to c) and d) as we did in class, and Loudon did in the text.
a) Draw the chair conformations of 1, 4 – ditertbutyl cyclohexane. b) Determine the most stable and least stable conformations. Explain your answer.
Strain of one Strain of one 1,3-diaxial interaction 1,3-diaxial interaction Strain of one 1,3-diaxial interaction H X Ph (C6H5) CO,H CN F 0.12 Me 0.9 1.5 Cl 0.7 0.1 0.25 Et 0.95 Br 0.25 i-Pr 1.1 OH 0.5 t-Bu 2.7
On the more stable conformations (number one part A drawing), can you label each of the carbons as primary, secondary, tertiary, or quaternary.
Draw 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.
which is the eclipsed conformation
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For the following molecule, draw both chair conformations. Using the rules of cyclohexane substituent stability, circle which is the more stable of the two
1. Compound 1 is one isomer of 1,3-dicholoro-2,4,6-triisopropylcyclohexane. a) Draw both chair conformations of compound 1. State which is more stable. (An isopropyl group should be treated as 'larger' than a chloro group.) b) Draw the most stable achiral stereoisomer of this compound, in its most stable conformation. c) Draw the most stable chiral stereoisomer of this compound, in its most stable conformation. i-Pr i-Pr 1 i-Pr 'CI
a) i) Draw the Newman projections for the conformations of ethane (staggered and eclipsed) Which is higher in energy? Which is more stable? Next to each conformer, draw the equivalent ‘sideways’ view, using wedged bonds

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