Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.19P
Consider rotation around the carbon-carbon bond in
a. Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.
b. Graph energy versus dihedral angle for rotation around this bond
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Students have asked these similar questions
Consider rotation around the carbon–carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).
a.Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.
b.Graph energy versus dihedral angle for rotation around this bond.
Sight along the C2-Cl bond of 2-methylpropane (isobutane).
a. Draw a Newman projection of the most stable conformation.
b. Draw a Newman projection of the least stable conformation.
c. Make a graph of energy versus angle of rotation around the C2-Cl bond.
d. Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.
Model 2. Cyclohexane Chair Conformation
Another helpful way to drawn a non-planar example of cyclohexane is to draw its most stable (lowest energy) conformation
called a chair conformation.
III
8.
Build two models of cyclohexane.
The chair conformation is the most stable conformation of cyclohexane because all of the bond angles around
the carbon atoms are at 109.5ª and all carbon atoms are in the more stable staggered conformation.
Cyclohexane is the only cyclic structure that allows all the bond angles around each carbon to be 109.5", thus is
the only ring that adopts a true chair conformation. Form the chair conformation with both of your
cyclohexane models. Look down each carbon carbon bond and verify that all carbons are in a staggered
conformation.
9.
10. Because of this conformation, there are two types of positions a group can occupy when it is attached to a
cyclohexane chair, either axial (A) or equatorial (E).
11. Axial hydrogens alternate straight up and straight down as we…
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - (a) Classify the carbon atoms in each compound as...Ch. 4 - Problem 3.3 Classify a carbon atom by the number...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Give the IUPAC name for each compound. a. c. b. ...Ch. 4 - Give the IUPAC name for each compound. a....
Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.12PCh. 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. 4.17PCh. 4 - a.Draw the three staggered and three eclipsed...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 - Draw a second chair conformation for each...Ch. 4 - Prob. 4.23PCh. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.26PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.29PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.32PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.35PCh. 4 - 3.31 For each alkane: (a) classify each carbon...Ch. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Give the IUPAC name for each compound. a. h.k....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. 4.42PCh. 4 - Prob. 4.43PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - Considering rotation around the bond highlighted...Ch. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - Prob. 4.52PCh. 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. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Which of the following compounds are lipids?Ch. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.74PCh. 4 - Prob. 4.75PCh. 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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- 1. Considering compounds that have the same number of carbon atoms, explain why alkanes and cycloalkanes have different molecular formulas but alkenes and cycloalkanes have the same molecular formulas. 2. Draw the condensed or line-angle structure for an alkene with the formula C5H10. 3. Draw the condensed or line-angle structure for 4 more C5H10 isomers (2 additional alkenes and 2 cyclic isomers).arrow_forwardConsider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?arrow_forward9) There are 3 different cyclopropane molecules with the formula GHĄC12. a. Draw and build the 3 molecules. b. Below each drawing, name each molecule with correct nomenclature. Label a pair that are constitutional isomers. d. Label a pair that are stereoisomers (or configurational isomers). С.arrow_forward
- Look at a cyclohexane model:a. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon 4. What is the resulting conformation? b. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon What is now the resulting conformation?arrow_forward4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forwardReplace one of the H atoms in the ethane model with a Br atom, to form ethyl bromide CH3CH2Br, and draw a projection (lewis) and a perspective drawing. Does replacing different hydrogen atoms in CH3CH3 to produce Ch3CH2br give you different isomers? (i.e. Are all the hydrogen atoms equivalent?) How many isomers of CH3CH2Br can you construct? Make a model of one other conformer of CH3CH2Br. DId you need to break any bonds to form the second conformer from the first?arrow_forward
- a. For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. ( see image) b.Draw and name the seven constitutional isomers (all contain a ring of some size) for cycloalkane, C6H12.arrow_forwardAnalyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.arrow_forwarda. Which of the following compounds can exist as cis–trans isomers? b. For those compounds that can exist as cis and trans isomers, draw and label the isomers. 1. CH3CH=CHCH2CH2CH3 2. CH3CH2C-CH2CH3=CHCH3 3. CH3CH CHCH3 4. CH3CH2CH CH2arrow_forward
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