EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 71P
For rotation about the C-3—C-4 bond of 2-methylhexane, do the following:
- a. Draw the Newman projection of the most stable conformer.
- b. Draw the Newman projection of the least stable conformer.
- c. About which other carbon-carbon bonds may rotation occur?
- d. How many of the carbon bonds in the compound have staggered conformers that are all equally stable?
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Students have asked these similar questions
For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.
b.Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d.Which isomer, cis or trans, is more stable and why?
Draw the most stable conformer of the following compounds, using Newman projections.
Choose the statement that is incorrect about
rings.
اختر احدى الاجابات
А.
Planar cyclobutane is its most stable
conformation.
В.
Planar cyclopentane would have small
angle strain but severe torsional strain.
C.
The chair conformation of cyclohexane has
no angle or torsional strain.
D.
Cyclopropane has the greatest angle
strain.
Е.
The chair conformation has less torsional
strain and fewer nonbonded interactions
than the twist boat conformation.
Chapter 3 Solutions
EBK ORGANIC CHEMISTRY
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 9PCh. 3.2 - Draw the structure for each of the following: a....Ch. 3.2 - Give each substituent on the nine-carbon chain a...Ch. 3.2 - Prob. 14P
Ch. 3.3 - What is each compounds systematic name?Ch. 3.3 - Prob. 16PCh. 3.3 - Prob. 17PCh. 3.3 - Prob. 18PCh. 3.3 - Prob. 19PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 21PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Prob. 25PCh. 3.6 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Draw condensed and skeletal structures for each of...Ch. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 32PCh. 3.9 - Prob. 33PCh. 3.9 - Prob. 34PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.10 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - Prob. 38PCh. 3.10 - Prob. 39PCh. 3.11 - a. Draw all the staggered and eclipsed conformers...Ch. 3.11 - Prob. 41PCh. 3.11 - Using Newman projections, draw the most stable...Ch. 3.12 - The bond angles in a regular polygon with n sides...Ch. 3.12 - Prob. 44PCh. 3.13 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.14 - Using the data in Table 3.9, calculate the...Ch. 3.14 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.15 - Prob. 48PCh. 3.15 - Which has a higher percentage of the...Ch. 3.15 - a. Draw the more stable chair conformer of...Ch. 3.15 - For each of the following disubstituted...Ch. 3.15 - a. Draw Newman projections of the two conformers...Ch. 3.15 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 56PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 66PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 69PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 72PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - What is each compound s systematic name?Ch. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 88PCh. 3 - Using the data obtained in Problem 85, calculate...Ch. 3 - Draw the conformers for the following...
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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
- yarrow_forwardConsider rotation around the carbon–carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).a. Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.b. Graph energy versus dihedral angle for rotation around this bondarrow_forwardWhich of the following represents the more stable chair conformer of the compound below? Question 1 Answer a. b. C. H₂C d. CH₂ Bo H₂C CH3 хоarrow_forward
- • Draw the chair conformations of the following compounds and determine which geometric isomer is more stable. Also show using Newman projection that one conformation is more stable than the other. a. cis-1-isopropyl-2-methylcyclohexane b. 1-methycyclohexanearrow_forwardPART II. BOND ROTATION IN BUTANE (STRUCTURES AND ENERGIES) Dihedral angle—eclipsed conformation 1. Relative energy—eclipsed 2. C1–C2–C3 bond angle—eclipsed 3. C1–C4 H–H distance—eclipsed 4. C2–C3 bond distance—eclipsed 5. C1–C2 bond distance—eclipsed 6. Dihedral angle—second eclipsed conformation 7. Relative energy—second eclipsed 8. C1–C2–C3 bond angle—second eclipsed 9. C2–C3 bond distance—second eclipsed 10.arrow_forward1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman projection and the chair drawing. Calculate the energies of each. What ratio of the two conformers will be present at equilibrium? 2. Draw a structure of a chiral alcohol.arrow_forward
- Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?arrow_forward4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forwardKindly draw the diagram neatlyarrow_forward
- For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d. Which isomer, cis or trans, is more stable and why? [1] [2] [3]arrow_forwardConsider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forward2. Use Newman Projections to represent the conformers of 1,2-dichloropropane and 2-bromo- 3-methybutane. (Draw the Newman Projections of these conformers and add respective photos in the space provided below) a. Conformers of 1,2-dichloropropane b. Confomers of 2-bromo-3-methylbutanearrow_forward
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