Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3.11, Problem 40P
a. Draw all the staggered and eclipsed conformers that result from rotation about the C-2—C-3 bond of pentane.
b. Draw a potential-energy diagram for rotation about the C-2–C-3 bond of pentane through 360°, starting with the least stable conformer.
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Consider the tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each six-membered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.
(a) Using Newman projections, draw all staggered and eclipsed conformations that result from rotation around the bond highlighted in red in each molecule; (b) draw a graph of energy versus dihedral angle for rotation around this bond.
Consider the attached tricyclic structure B.
(a) Label each substituent on the rings as axial or equatorial.
(b) Draw B using chair conformations for each sixmembered ring.
(c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.
Chapter 3 Solutions
Organic Chemistry (8th Edition)
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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- using newman projections draw the least and most stable conformations with respect to the bond indicated 1-hexyne (C3 is front carbon and C4 is back carbon)arrow_forwardSight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forwardDraw the planar (Haworth) structure for cis-1-ethyl-2- methylcyclohexane. (b) Draw the two ring - flipped chair conformations. (c) Circle the more stable chair conformation (circle both if they are equal in energy). Draw the Haworth structure and the two ring-flipped conformations of 1, 2, 4- trimethylcyclohexane (Compound D) on the frames below, b) Circle the more stable chair conformation (circle both if they are equal in energy). Haworth Structurearrow_forward
- Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2¬C3 bondarrow_forwardstarting from the wedge and dash structure below, rotate the back carbon to provide the newman projection in the least stable conformationarrow_forwardAmong the figure, (a) what is the most stable conformation of n-pentane? (b) gauche conformation of butane and (c) least stable conformation of butanearrow_forward
- Label each ring in Figure 7.2 cis or trans.arrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forwardOn the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25). (a) Convert the stereorepresentation on the left to a planar hexagon representation. (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?arrow_forward
- Draw a cyclohexane chair with 2 substituents that requires a chair flip.arrow_forward(a) (R)-1,1,2-trimethylcyclohexane, draw a three-dimensional representation.arrow_forwardConstruct a qualitative potential energy diagram for rotation about C-C bond of 1,2-dibromoethan. Which conformation would you expect to be more stable? label the anti and gauche conformation of 1,2-dibromoethanearrow_forward
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