Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
7th Edition
ISBN: 9780134240152
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3.10, Problem 37P
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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Draw the staggered and eclipsed conformations that result from rotation around the C–C bond in CH3–CH2Br.
PART 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.
Interconversion of the staggered and eclipsed conformations of alkanes
requires rotation around a -C bond such as the one depicted below (see arrow).
Using your knowledge of bonding, explain why these rotations do not significantly
affect the energy (strength) of these bonds. You may find it helpful to describe the
type of bond being rotated.
Chapter 3 Solutions
Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th 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. 11PCh. 3.2 - Prob. 12PCh. 3.3 - Prob. 13PCh. 3.3 - Prob. 14P
Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 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. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - 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. 53PCh. 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. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 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 - Prob. 80PCh. 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. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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- How To Draw the Two Conformations for a Substituted Cyclohexane ?arrow_forwardPlease don't provide handwriting solutionarrow_forwardUsing Newman projections and an energy diagram, draw all of the conformers of 1,1,2- tribromoethane and indicate the energy changes that arise from rotation about the C-C bond. You do not need the actual energy values, but you should label relative energies (energy minima and maxima).arrow_forward
- What is the preferred IUPAC name of the alkene shown in Figure below? CH3 CH3 CH3 `CH-CH3 A. 1-ethyl-2,4,5-trimethylcyclohexene B. 2-ethyl-1,4,5-trimethylcyclohexene C. 2-ethyl-1,4,5-trimethylcyclohex-1-ene D. 4-ethyl-1,2,5-trimethylcyclohexenearrow_forwardWhich of the following statements regarding cycloalkanes is wrong? a. The least strained form of any unsubstituted cycloalkane is the boat conformation of cyclohexane b. The planar form of any cycloalkane with a ring larger than cyclopropane will not be the most stable conformation c. Cyclopentane is nonplanar to avoid the torsional strain between adjacent C-H bonds. d. A di-substituted cycloalkane can have cis-trans isomers.arrow_forwardWhat is angle strain in cycloalkanes? Angle strain is the difference between an ideal bond angle for sp3 hybridized carbon atoms and the actual bond angle in the ring. Angle strain is the difference between and ideal bond angle for sp hybridized carbon atoms and the actual bond angle in the ring. Angle strain is the angle between C-C bonds in the cycloalkane ring. Angle strain is the angle between carbon bonds on the outer side of a cycloalkane ring. Angle strain is the difference between the C-C bond angles found in a flat ring structure and in an actual ring structurearrow_forward
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