Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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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.
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b
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.
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
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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- 1. 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_forward1) RCO H 2) [H₂SOJ. ? Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. H₂C. OH th CH, CH₂ OH H₂C OH aff CH₂ CH₂ Edit Drawingarrow_forwardjarrow_forward
- 5) Identify the least stable conformation of 3-bromo-2-methylpentane, viewed through the C3 - C4 bond (ie. C3 in front and C4 in the back). CH3 CH3 CH3 Br CH2CH3 Br. H. Br. H. CH3 CH 3 H. CH(CH3)2 H. CH2CH3 I II III CH(CH3)2 Br H Br. CH3 H. H CH(CH3)2 IV Varrow_forwardPut them in right categoryarrow_forwardLabel a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. HI ||| H Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 2: Identify the Newman projections for each rotation (continued). As the back carbon rotates, the Newman projections alternate from staggered to eclipsed and back again. Fill in the remaining conformations for each conformation labeled with the angle of internal rotation from the starting Newman projection. Starting structure - 0° 120° 180° CH3 H₂C H H Answer Bank CH3 -CH3 CH3 H CH3 □ O CH3 O 240° 300° CH3 CH3 DFØ CH3 H CH3 CH3 H CH3arrow_forward
- 2. For the two compounds below, draw the two possible conformations. Circle the conformation(s) that would be the most stable. Remember, though A values were developed for cyclohexanes, they are a good guide for other types of rings as well! OH ço OEt ll pharrow_forwardpt. 4: Molecular Models: Stereoisomers me: 4. Using the model of 2-bromobutane representing the R enantiomer from 4., switch any two groups on the chiral carbon. Compare this to your S enantiomer from 4. a. Are they the same or different? b. Are they the same or enantiomers? C. Now switch any pair of groups around the chiral carbon of the "switched" model again! Compare the "double-switched" model with the other unmodified S molecule from 4. Are they enantiomers or are they identical? С. Shown below is the Fisher projection of (R)-2-bromo-(S)-3-chlorobutane. ne mirror image of this stereoisomer and assign the RIS configurations of iral carbons for both isomers. е ll erarrow_forward+ 1. Draw line structures of all of the C3H17* carbocations that have the carbon skeleton shown below. 2. Circle the most stable carbocation of those that you have drawn.arrow_forward
- What is the relationship (resonance structures, constitutional isomers, conformational isomers, enantiomers, meso compounds, diastereomers, or none of these) between the pair of structures below? 4. а. b. C. CI 5. Circle the most stable conformer of (S)-3,3-dimethyl-2-hexanol. H CH3 CH3 H CH3 (CH2)2CH3 H3C(H2C)2CH3 H3C(H2C)2 CH3 H3C H3C(H2C)2 H3C CH2CH3 CH3 H3C OH H OH H HO, HO CH3 H H,C CH3 ČH2CH3 CH3 6. Circle the compound(s) that is/are optically active (a chiral molecule). (CH2)3CH3 H. HO ČH3 :11 1.arrow_forward1. Convert the following rings into their chair forms (original & flip) CH3 b) OH Brarrow_forwardWhich carbocation below is/are the most stable one? Circle it (them)arrow_forward
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