Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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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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Make a model of cyclohexane and draw its shape. Comment on its bond angles and how easily the model fitted together. Draw the boat and chair conformations of cyclohexane. Which arrangement do you think is the most stable?
Calculate the destabilization present in each eclipsed conformation. (See attachment)
In the drawing areas below, draw the two conformations of bromocyclohexane that are typically the most stable. Be sure your
drawings make it possible to distinguish between the conformations.
After you've drawn the conformations, answer the question below the drawing areas.
G
chair flip
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drawing a structure.
Of the two conformations you drew above, which is
the more stable?
O left
O right
◇ they are equally stable
cannot decide without more
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X
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drawing a structure.
C
Chapter 3 Solutions
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. 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_forwardDraw the two chair conformations for each of the following compounds and indicate which conformer is more stable.arrow_forwardWhich of the following statements are correct? * Conformation exist in a dynamic equilibrium state. Conformers differ largely in energies. Conformers cannot be separated. Amount of more stable conformers is more than that of less stable conformers at equilibrium.arrow_forward
- Please 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_forwardWhat 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_forward
- Look at a cyclohexane model:a. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon 4. What is the resulting conformation? b. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon What is now the resulting conformation?arrow_forwardThe octane rating for gasoline is a measurement of how readily a fuelcombusts compared to 2,2,4-trimethylpentane, an isomer of octane.a. Draw 2,2,4-trimethylpentane and verify that it is an isomer ofoctane.b. Draw four other isomers of octane.c. Select one of the isomers and draw it such that it looksdifferent on the page but is still the exact same compound.d. Name this isomer.e. Define isomer using a complete sentence.arrow_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_forward
- What 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_forwardDraw all constitutional isomers of C6H14. Draw all isomers of cycloalkanes with molecular formula C5H10. Include cis/trans isomers.arrow_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_forward
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