Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 6, Problem 1E
Interpretation Introduction
Interpretation:The Newman projection of butane in its least favorable conformation is to be determined.
Concept introduction:
Newman Projection is useful for the alkaline stereochemistry. The confirmation of this projection is helpful to visualize the bond of the structure from front to back or rear.
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Students have asked these similar questions
Compare the following conformers of butan-2-ol. Match each conformer to their
corresponding relative energy. Recall, the more stable the conformer the lower the
energy.
1.
ОН
CH3
CH3
H
2nd Highest Energy
2.
HỌH
CH3
2nd Lowest Energy
H3C
OH
Highest Energy
3.
H3C.
CH3
Lowest Energy
OH
H.
CH3
4.
>
4. For the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse
structures corresponding to the lowest and highest energy conformations for rotation around the
C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3
CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference
between the lowest and highest conformations, and be sure to clearly show each energy
contribution that you are including in your calculation.
Lowest Energy Conformation
3-D sawhorse
Newman
ECLIPSING
Interactions
Energy Difference:
AB
Energy
kcal/mol
H/H 1.0
H/Me 1.4
H/Et 1.5
H/Pr 1.6
H/1-Bu 3.0
Me / Me 2.6
Me/Et 2.7
Me/i-Pr 3.0
GAUCHE A
Interactions
Energy
kcal/mol
Me / Me 0.9
Me / Et 0.95
Me/i-Pr 1.1
Me/t-Bu 2.7
Et/Et 1.1
Et/i-Pr 1.6
Et/t-Bu 3.0
i-Pr/i-Pr 2.0
Highest Energy Conformation
3-D sawhorse
Newman
1
Then draw the most stable and least stable Newman projection conformation from the C4-C5 bond in the molecule above
Chapter 6 Solutions
Organic Chemistry: A Guided Inquiry
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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- 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.arrow_forwardFor the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. 2,3-dimethylpentane ECLIPSING Interactions AB Energy kcal/mol H/H 1.0 H / Me 1.4 H/Et 1.5 H/i-Pr 1.6 H/t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Me/i-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et / -Pr Et/t-Bu i-Pr/i-Pr B Energy kcal/mol 0.9 0.95 1.1 2.7 1.1 1.6 3.0 2.0arrow_forwardFor the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions AB H/H H/Me H / Et H/i-Pr Energy kcal/mol 1.0 1.4 1.5 1.6 H/ t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Mei-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et/i-Pr Et / t-Bu i-Pr/i-Pr 3-D sawhorse Energy kcal/mol Newman 0.9 0.95 1.1 2.7 1.1 1.6 Highest Energy Conformation 3.0 2.0arrow_forward
- translate the bond-line notation structure to the Newman projection by filling int the missing groups (A, B, C, D or E) on the lines in the Newman projection so they match the conformation given in the original structure. Circle if the conformation is a staggered or eclipsed.arrow_forwardClick on all of the following Newman projections that represent the least stable conformation of 2,2,3-trimethylbutane . CH3 HCH3 H3CCH3 CH3 CH3 CH3 CH3 H3C, CH3 H. H. H3C* ČH3 CH3 H3C ČH3 CH3 CH3 CH3 H3C ČH3 CH,arrow_forward4. Draw the most stable chair conformation of the following disubstituted cyclohexane. Draw carefully positioned intersecting arcs to denote all sources of steric strain for this conformation. CH3 CH3arrow_forward
- 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 andunderline the lowest energy conformation.arrow_forwardDraw the most stable conformation of the disubstituted cyclohexane below.arrow_forwardFill on each conformation of (R)-2-chlorobutanearrow_forward
- 2. Circle the compound that would have the lowest energy at its most stable conformation and box the compound that would have the highest energy at its most stable conformation. 호호호호arrow_forward(5) Draw the most stable chair conformation of the cyclohexane shown below. CH3 CI H3C Br OH CH3arrow_forward5. If two groups in a disubstituted cyclohexane are not the same, then the more stable conformation is the one in which the largest group is equatorial. Draw the most stable chair conformation for each of the following compounds. Use the given templates. Note that the carbon numbers are given and each template has the carbon numbers placed differently. (a) a. cis-1-tert-butyl-4-methylcyclohexane b. trans-1-tert-butyl-4-methylcyclohexane c. trans-1-isopropyl-3-methylcyclohexane 4 5 6 3 2 (b) 3 4 5 2 1 6 (c) 3 2 1 4 6 5arrow_forward
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