On a separate sheet of paper, draw the two alternative chair conformations for the product formed by the addition of bromine to 4-tert- butylcyclohexene. The Gibbs free-energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ/mol for tert-butyl, and 2.3 kJ/mol for bromine.. Calculate the ratio of the two observed products at 46.0 °C using the following equation: AG-RT In Ke The gas constant, R, is 8.314 3/K-mol. (Enter your answer to two significant figures.) Ratio: to 1 Major Submit Answer Minor Try Another Version 5 item attempts remaining

On a separate sheet of paper, draw the two alternative chair conformations for the product formed by the addition of bromine to 4-tert- butylcyclohexene. The Gibbs free-energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ/mol for tert-butyl, and 2.3 kJ/mol for bromine.. Calculate the ratio of the two observed products at 46.0 °C using the following equation: AG-RT In Ke The gas constant, R, is 8.314 3/K-mol. (Enter your answer to two significant figures.) Ratio: to 1 Major Submit Answer Minor Try Another Version 5 item attempts remaining

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 61AP: Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of...

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On a separate sheet of paper, draw the two alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free-energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kl/mol for tert-butyl, and 2.3 k/mol for bromine. Calculate the ratio of the two observed products at 48.0 "C using the following equation: AG --RT In Ka The gas constant, R, is 8.314 J/K-mol. (Enter your answer to two significant figures.) Ratio: to 1 Major Minor
On a separate sheet of paper, draw the two alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free-energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ/mol for tert-butyl, and 2.3 kJ/mol for bromine. Calculate the ratio of the two observed products at 46.0 °C using the following equation: AG-RT In Keq The gas constant, R, is 8.314 J/K.mol. (Enter your answer to two significant figures.) Ratio: Major to 1 Minor
On a separate sheet of paper, draw the two alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free-energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ/mol for tert-butyl, and 2.3 kJ/mol for bromine. Calculate the ratio of the two observed products at 32.0 °C using the following equation: AG° = -RT In Keg The gas constant, R, is 8.314 J/K mol. (Enter your answer to two significant figures.) Ratio: to 1 Major Minor
Draw the alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ (4.9 kcal)/mol for tert-butyl and 2.0–2.6 kJ (0.48–0.62 kcal)/mol for bromine. Estimate the relative percentages of the alternative chair conformations you drew in the first part of this problem
Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energy
Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.
An alkene having the molecular formula C₂H₁4 is treated sequentially with ozone (03) and zinc/acetic acid to give the product/s shown. Draw a structural formula for the alkene. NO O You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. . 99.85 ...ll Sn [F ChemDoodleⓇ 136
Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle
2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: a. NO NID ALOH 1) NaCN 2) H+ 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?
Compound A, C₂H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: O CH3 O || CH3CCH₂CCH₂CCH3 CH3 Compound A Propose a structure for A. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.
DHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?
2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.