ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.54P
Draw the two possible chair conformations for
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What chair structure corresponds to the highest energy conformation of trans-1,4-dichlorocyclohexane (shown on left)?
CI
CI
CI
CI
CI CI
CI
.CI
CI A
C
D
CI
B
O O O O
Which staggered conformation(s) has (have) the lowest energy? Which has (have) the highest energy?
Consider the isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert-butylcyclohexanol and two are
cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four
conformations is the most stable.
FIX a box
OH
HO
OH
A
Select the more stable conformation of
cis-2-tert-butylcyclohexanol.
B
OD
C
B
C
D
☐A
C
OH
Select the more stable conformation of
cis-3-tert-butylcyclohexanol.
Chapter 4 Solutions
ORGANIC CHEMISTRY
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- Draw the structure for the most stable chair conformation of trans-1-tert-butyl-3-chlorocyclohexane. Use the cyclohexane conformation drawing tool and guide points to draw each structure. C1 M C™ X Ĉarrow_forwarddraw a stable conformation of this compoundarrow_forwardFollowing 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. H,C CH3 H H H CH3arrow_forward
- Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H₂C H (H3C) 3C H H CH3 →arrow_forwardBelow are isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert- butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four conformations is the most stable. A OH Ex HO B D OH OHarrow_forwardConstruct the chair structures with the molecular models for trans-1-ethyl-3-methylcyclohexane. Find the energy of each conformer, the equilibrium constant Keq, and the percentage of each conformer at 25oC. Indicate which conformer is more stable.arrow_forward
- In the lowest energy chair conformation of cis-1,3-dimethylcyclohexane, how many axial positions are occupied by hydrogen atoms? * O 2arrow_forwardFor trans‑1‑ethyl‑4‑isopropylcyclohexane, which structures represent the possible boat conformations?arrow_forward11. Which one of these forms of 1,2,4-trimethylcyclohexane can have a chair conformation in which the methyl groups are all equatorial? III ++ |||| A B с D Earrow_forward
- Perspective drawings of Chair and Boat Conformers fo Cyclohexane (C6H12). Note it is impossible to place all the carbons in the same plane without straining the bonds. Take two opposite carbons and pull both of them up to make one conformation adn then pull one of them down to make the other conformation. Can you inercovert one conformer int othe other without breaking any bonds? Explain why these represent conformers and not isomers.arrow_forwardCyclohexane structures can have two chair conformations. Draw the alternate conformation of the structure shown below. Rotations of the structure are not allowed. H3C CF3arrow_forwardFollowing is the Structural formal of Chloropropane H H H 2. H Draw Newman projections for all staggered and eclipsed conformation formed by rotation about C1 - C2 bond from 0° to 360°. b) Which Staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest energy?arrow_forward
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