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Problem 3-48 For each of the following compounds, draw an isomer that has the same functional groups. (a) CH3 CH3CHCH2CH2Br -OCH3 (b) Problem 3-52 Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3.5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane Problem 3-42 Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond: (a) Draw a Newman projection of the most stable conformation. (b) Draw a Newman projection of the least stable conformation. Problem 3-44 Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2- dibromoethane. Problem 3-45 Which conformation of 1,2-dibromoethane (Problem 3-44) would you expect to have the largest dipole moment? The observed dipole moment of 1,2-dibromoethane is µ = 1.0 D. What does this tell you about the actual conformation of the molecule?

Problem 3-48 For each of the following compounds, draw an isomer that has the same functional groups. (a) CH3 CH3CHCH2CH2Br -OCH3 (b) Problem 3-52 Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3.5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane Problem 3-42 Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond: (a) Draw a Newman projection of the most stable conformation. (b) Draw a Newman projection of the least stable conformation. Problem 3-44 Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2- dibromoethane. Problem 3-45 Which conformation of 1,2-dibromoethane (Problem 3-44) would you expect to have the largest dipole moment? The observed dipole moment of 1,2-dibromoethane is µ = 1.0 D. What does this tell you about the actual conformation of the molecule?

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.SE: Something Extra
Problem 56AP: How many cis–trans stereoisomers of myo-inositol (Problem 4-55) are there? Draw the structure of...
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Problem 3-48 For each of the following compounds, draw an isomer that has the same functional groups. (a) CH3 CH3CHCH2CH2Br -OCH3 (b) Problem 3-52 Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3.5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane
Transcribed Image Text:Problem 3-48 For each of the following compounds, draw an isomer that has the same functional groups. (a) CH3 CH3CHCH2CH2Br -OCH3 (b) Problem 3-52 Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3.5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane
Problem 3-42 Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond: (a) Draw a Newman projection of the most stable conformation. (b) Draw a Newman projection of the least stable conformation. Problem 3-44 Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2- dibromoethane. Problem 3-45 Which conformation of 1,2-dibromoethane (Problem 3-44) would you expect to have the largest dipole moment? The observed dipole moment of 1,2-dibromoethane is µ = 1.0 D. What does this tell you about the actual conformation of the molecule?
Transcribed Image Text:Problem 3-42 Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond: (a) Draw a Newman projection of the most stable conformation. (b) Draw a Newman projection of the least stable conformation. Problem 3-44 Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2- dibromoethane. Problem 3-45 Which conformation of 1,2-dibromoethane (Problem 3-44) would you expect to have the largest dipole moment? The observed dipole moment of 1,2-dibromoethane is µ = 1.0 D. What does this tell you about the actual conformation of the molecule?
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