Custom eBook for Organic Chemistry
2nd Edition
ISBN: 9798214171104
Author: Straumanis
Publisher: Cengage Custom
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Textbook Question
Chapter 6, Problem 3E
Using your model of butane
a. Label each Newman projection of butane on the graph with the words staggered, eclipsed, gauche, and anti, as appropriate. (Note that some structures will have more than one label.)
b. Draw a wedge and dash bond representation of butane in its lowest P.E. conformation.
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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.
. Consider the hash/wedge structure below.
a. Draw the Newman projection of the bond indicated, keeping the conformation
the same.
НО
b. Draw the Newman projection for the most stable conformation
CI
c. In the Newman projection for part b, label all gauche interactions.
Use flat representation of rings, not chair in the drawing. Determine the most and least stable.
Consider the most stable chair for each of these isomers, and then draw the most stable and least stable isomer based on a comparison of the best chair for each one.
Chapter 6 Solutions
Custom eBook for Organic Chemistry
Ch. 6 - Prob. 1CTQCh. 6 - Prob. 2CTQCh. 6 - Prob. 4CTQCh. 6 - Prob. 5CTQCh. 6 - Complete this graph of relative potential energy...Ch. 6 - Prob. 7CTQCh. 6 - Prob. 8CTQCh. 6 - Prob. 9CTQCh. 6 - Consider the Newman projection below. a. Draw a...Ch. 6 - Draw a Newman projection showing the lowest P.E....
Ch. 6 - Prob. 12CTQCh. 6 - Prob. 13CTQCh. 6 - In skeletal representations the hydrogens are not...Ch. 6 - Prob. 15CTQCh. 6 - Prob. 16CTQCh. 6 - Prob. 17CTQCh. 6 - Prob. 19CTQCh. 6 - Prob. 20CTQCh. 6 - Prob. 21CTQCh. 6 - Prob. 22CTQCh. 6 - Prob. 23CTQCh. 6 - Draw a constitutional isomer of pentane,...Ch. 6 - How many H’s are lost from the molecular formula...Ch. 6 - How many ifs are lost from the molecular formula...Ch. 6 - Prob. 27CTQCh. 6 - What is the degree of unsaturation for the example...Ch. 6 - Without counting hydrogens, determine which one of...Ch. 6 - Determine the degree of unsaturation (and draw a...Ch. 6 - a model of each molecule shown above: Is the...Ch. 6 - Prob. 32CTQCh. 6 - Prob. 33CTQCh. 6 - Label each double bond E, Z, or neither. (It may...Ch. 6 - Prob. 35CTQCh. 6 - Prob. 36CTQCh. 6 - Indicate the relationship between each pair....Ch. 6 - Prob. 38CTQCh. 6 - Prob. 1ECh. 6 - Prob. 2ECh. 6 - Using your model of butane (CH3CH2CH2CH3) ,...Ch. 6 - Consider the molecule 1-bromo-2-methylbutane. C3...Ch. 6 - Prob. 5ECh. 6 - Prob. 8ECh. 6 - Prob. 9ECh. 6 - Prob. 10ECh. 6 - Prob. 11ECh. 6 - Prob. 12ECh. 6 - Prob. 13ECh. 6 - Prob. 15ECh. 6 - Prob. 16ECh. 6 - Prob. 17ECh. 6 - Prob. 18ECh. 6 - Prob. 19ECh. 6 - Prob. 20ECh. 6 - Prob. 21ECh. 6 - Double bonds do not rotate freely under normal...Ch. 6 - up an example (not appearing in this ChemActivity)...Ch. 6 - Prob. 24ECh. 6 - Prob. 25E
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- 4. For the following structures, draw both possible chair conformations, using a ring flip to go from one to the other, and circle the one that is most stable/lowest energy. (Hint: Use Table 4.8 in Klein.) Show all groups, including hydrogen atoms, attached to the cyclohexane ring. А. Me Me Et В. Et t-Bu Etarrow_forwardQ2. a) Draw the Newman projection of the most stable staggered conformation of 2-methylpentane, looking down the 3,4 bond. H3C c-CH2-CH2CH3 H3C´H b) The structure of cis-1-tert-butyl-3-methylcyclohexane is shown below. Draw both chair forms of this molecule, and circle the one you think is less stable. Me 't-Buarrow_forwardH3C H. NHCH3 NHCH3 H Harrow_forward
- A. Using your molecular modeling kit, construct trans-1,4-dimethylcyclohexane. In the space below, draw one of the chair conformations. Label the methyl groups as either axial (a) or equatorial (e). Number the carbons of the cyclohexane ring, perform a chair flip and draw the new chair conformation.arrow_forward3. Draw Newman projection for the highest and lowest energy conformers of your assigned molecule. Provide a rationale to support your answer. In other words, why is the highest energy conformer so high in energy? Why is the lowest energy conformer low in energy? Molecule (2R,3S)-2-Bromo-3- Floro butanearrow_forwardPossible Newman projection for following?arrow_forward
- C. Using your molecular modeling kit, construct cis-1,4-dimethylcyclohexane. In the space below, draw one of the chair conformations. Label the methyl groups as either axial (a) or equatorial (e). Number the carbons of the cyclohexane ring, perform a chair flip and draw the new chair conformation.arrow_forward1. Draw the most and least stable Newman projections for the following molecules (focus on C2 and C3). a. 2-chloro-2-fluoropentane b. 2,2-dimethylbutane c. 2-chloro-2-methylpentane d. 1,2-dibromoethanearrow_forwardDraw the most and least stable Newman projections for the following molecules ( focus on C2 and C3). a. 2-chloro-2- fluoropentane b. 2,2-dimethylbutane C. 2-chloro-2-methylpentane d. 1,2-dibromoethanearrow_forward
- 3. For pentane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.arrow_forward5. Chairs and E2 b. a. Draw the line-bond structure of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Draw both chair flips of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Showing all calculations, determine which is the more stable conformation. C. Which chair flip is able to undergo E2 elimination? Justify your answer. d. Show the product of such an E2 elimination using NaOEt as base.arrow_forwardSight 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.arrow_forward
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