Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3.14, Problem 47P
The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C-1—C-2 bond?
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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.
Select the more stable conformation overall.
D
A.
The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C-1¬C-2 bond?
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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- Arrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forwardFollowing are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardViewed through the C-3 — C-4 bond, which is the most stable conformation of 3-bromo-2-methylpentane?arrow_forward
- Draw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forwardWhat is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?arrow_forwardGiven the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C, H H D How is Compound D related to the chair conformation? H3C. O It is a constitutional isomer. -CH3 O It is not an isomer. O It is a conformation isomer (conformer). O It is a stereoisomer.arrow_forward
- Consider a Newman Projection for 2,2,3-trimethylbutane. Which of the following is true? The least stable conformation of the molecule has 22 kJ/mol of straih energy. The least stable conformation has 28 kJ/mol of torsional strain energy. The most stable conformation of the molecule has two gauche butane interactions with 7.6 kJ/mol of strain energy. The most stable conformation of the molecule has no torsional strain interactions. O O O Oarrow_forward2-fluoro-2-methylcyclohexane O 1-fluoro-1-methylcyclopentane 2-fluoro-2-methylcyclopentane O 1-fluoro-1-methylcyclohexane This is the General Formula for alkenes, where n is the number of C. CnH2n CnH2n-2 CnH2n+2 CnH2n-4 The number of degrees of unsaturation of this compound. 3arrow_forwardGiven the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C, H How is Compound C related to the chair conformation? CH3 H3C. It is a constitutional isomer. It is a conformation isomer (conformer). It is a stereoisomer. ČH3 It is not an isomer.arrow_forward
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