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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Calculate the destabilization present in each eclipsed conformation. (See attachment)
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.
Write the energy diagram corresponding to each conformer by writing the conformers (and Newman projection formulas) formed by the rotation of the bond between the carbon 3 and 4 (C3 and C4) of the 2-methylpentane. Indicate the most stable and unstable conformers.
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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- 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.arrow_forwardIn 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 Click and drag to start 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 information X X Click and drag to start drawing a structure. Carrow_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_forward
- Draw the two chair conformations for each of the following compounds and indicate which conformer is more stable.arrow_forwardPlease don't provide handwriting solutionarrow_forwardConsider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc. a.Which conformer is the most stable? the least stable? b.Which rotamer is the anticonformer? the gaucheconformer? c.Draw the anticonformer in saw horse projection.arrow_forward
- Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper toward the viewer. A hatched wedge points back from the plane of the paper away from the viewer.)arrow_forwardLook 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_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
- • 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_forwardWhich of the following statements regarding cycloalkanes (Cyclopropane through Cyclopentane) are FALSE.arrow_forwardOut of CH3—NH2 and (CH3)3N, which one has higher boiling point?arrow_forward
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