Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 3, Problem 86P
Using the data obtained in Problem 85, calculate the amount of steric in each of the chair conformers 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?
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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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- calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?arrow_forwardacyclic conformersarrow_forwardDraw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997) Provide a reason for your choice by identifying all of the interactions that led to your decision. H₂C OH C₂ HO CH3 Which of the following is the most stable staggered conformer? Me Me *** Conformer B Me- Me Conformer A Me Conformer C Me Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.arrow_forward
- Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.arrow_forwardWhich of the following is the most stable conformation of the following compound? T IVarrow_forwardAs we learned, monosubstituted cyclohexanes exist as anequilibrium mixture of two conformations having either an axial orequatorial substituent. When R = CH2CH3, Keq for this process is 23.When R = C(CH3)3, Keq for this process is 4000. Question: a.) Which R shows the higher percentage of axial conformation at equilibrium?arrow_forward
- Which of the following is the most stable conformation of trans-1-isopropyl-3-methylcyclohexane? IVarrow_forward6) Draw the energetically favored (more stable) chair conformer of the following cyclohexane. H3C OH 110arrow_forwardProvide the most stable (lowest energy) chair conformation of methylcyclohexanearrow_forward
- What is the most stable conformation of the given trisubsituted cyclohexane?arrow_forwardWrite the structures of two chair conformations of 1-tert-butyl-1-methylcyclohexane. Which conformation is more stable?arrow_forward13 Draw the molecule trans-1-ethyl-3- isopropylcyclohexane conformation. Which is the overall most-stable conformer? Justify your answer. in its chair and its flipped chairarrow_forward
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