Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 4, Problem 4.29P

Draw a chair conformation of cyclohexane with one CH 3 CH 2 group and

one CH 3 group that fits each description.

a. a 1, 1-disubstituted cyclohexane with an axial CH 3 CH 2 group

b. a cis-1, 2-disubstituted cyclohexane with an axial CH 3 group

c. a trans-1, 3-disubstituted cyclohexane with an equatorial CH 3 group

d. a trans-1, 4-disubstituted cyclohexane with an equatorial CH 3 CH 2 group.

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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?
4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3C

Chapter 4 Solutions

Organic Chemistry

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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