Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 6, Problem 9CTQ
(a)
Interpretation Introduction
Interpretation:
The most stable conformation of butane rotating around
Concept Introduction:
The three-dimensional arrangement of atoms and molecules in space is known as stereochemistry.
(b)
Interpretation Introduction
Interpretation:
The explanation for most stable conformation names should be given.
Concept Introduction:
The three-dimensional arrangement of atoms and molecules in space is known as stereochemistry.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
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
2. Convert the line structure of 2,3-dimethylpentane into a Newman projection as viewed along the
C2-C3 bond (C2 in front, C3 in back). Draw the most stable conformation. Two templates are given
with one hydrogen atom drawn in place. Note that only one template leads to the correct answer,
therefore use only one of the given templates.
t
Н.
H.
b. Draw a Newman projection of the given compound H viewed from C-2 to C-3 orientated according to the first template. Then use the
Newman projection to demonstrate the most stable conformation around the C2-C3 bond according to the second template.
(Hint:
Order of decreasing group size 'Pr > CH2CH3 > CH3 > OH > Br > H]
NH2
Me
Ме
H
'Pr
Given conformation
Most stable conformation
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 3. Chair conformation time! Consider the following molecule: Ph. iPr NH₂ a. Circle the largest substituent. b. Now take this largest substituent and place it equatorial on one of the cyclohexane rings drawn below. It does not matter which ring you pick first. c. Now move clockwise (or counterclockwise if you're rebellious) around the chair conformation you chose, drawing in the rest of the substituents (including hydrogens). i. Remember, wedges and dashes only indicate up or down here, not axial or equatorial. You can be axial up, equatorial up, axial down, or equatorial down. d. Now look at the chair conformation you left blank. Draw the largest substituent axial on this ring. e. Repeat c, moving along the rest of the chair conformation to draw in the rest of the substituents, including hydrogens. f. Label the most stable conformation: it should be the conformation with the most and/or largest substituents equatorial. #4arrow_forwardOrder the following in increasing priority A. -C, -CH, -OL B. -CH3, -CH2OH, -CH2CH3 C. -C≡CH, -CH゠CH2, -CH゠Oarrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a. Label the substituents on C1, C2, and C4 as axial or equatorial.b. Are the substituents on C1 and C2 cis or trans to each other?c. Are the substituents on C2 and C4 cis or trans to each other?d. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward
- Consider the substituted cyclohexane shown in the ball-and-stick model.a.Label the substituents on C1, C2, and C4 as axial or equatorial. b. Are the substituents on C1 and C2 cis or trans to each other? c.Are the substituents on C2 and C4 cis or trans to each other? d.Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forwarda. Draw the structure of this molecule as a hexagon with dash(es) and/or wedge(s). ha -OH b. Draw the other chair conformation. c. Draw the enantiomer of the molecule in its most stable conformation. он H d. Ignoring differences in conformation, how is this molecule related to the one above? Are they the Same molecule, Enantiomers, or Diastereomers? OH H₂ HH₂ POM (CH₂)2arrow_forwardIn the equilibrium shown, trans-1,2-dimethylcyclohexane conformer A has which steric interactions? B a. One gauche, two 1,3-diaxial ob.One gauche; zero 1,3-diaxial Oc. Zero gauche, four 1,3-diaxial od. One gauche, four 1,3-diaxial Oe. Zero gauche, two 1,3-diaxialarrow_forward
- a. Draw clear structures of all the possible distinct 2,3-dibromobutane isomers that can be formed. b. identifying the absolute stereochemistry of each stereocenters. c. Indicate the relationships between each of the structures you have drawn (enantiomers, diastereomers, etc.). d. Choose the (2R,3R)-dibromobutane and draw the most stable and the least stable Newman projection looking at C2-C3 sigma bond.arrow_forward1. Draw a Newman projection of the most stable conformational isomer of 2,4-dimethylhexane as viewed along the C3-C4 bond (C3 in front, C4 in back). Two templates are given with one hydrogen atom drawn in place. Note that only one template leads to the correct answer, therefore use only one of the given templates. H H.arrow_forwarda. Draw trans-1-ethyl-2-methylcyclohexane in its lowest energy conformation. Choose a chair from the Templates toolbar at the bottom. Make sure it’s the appropriate chair, including any heteroatoms. Replace the appropriate hydrogens with the appropriate −CH3−CH3 or other groups. b. Draw the structure that corresponds with the name: isobutylcyclopentane.arrow_forward
- Consider the cyclohexane framework in a chair conformation, where carbon 1 has two substituents, X and Y. a. Label each position as axial or equatorial. b. On the same figure, label all positions that are gauche to the Y group on carbon 1. A bin may hold more than one label. axial equatorial X 1 equatorial equatorial 2 axial axial axial gauche 3 axial gauche 5 equatorial equatorial 4 axial equatorial Answer Bank equatorial gauche axialarrow_forward| 16. Which conformation of cyclohexane experiences the most transannular strain? a. chair b. planar c. boat d. twist boat e. All of these are stable. basdarrow_forwardbn 6. a.) Classify the following carbocations (1°, 2°, or 3°). b.) Encircle the carbocation/s that can rearrange to a more stable structure. smib-t.-S) CH3 CH3 CH3 CH2 CH2 CHz-C+ CH3arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning