Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 67AP
Interpretation Introduction
Interpretation:
Cyclitols are cyclic polyols.
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On a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- 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.arrow_forwardWrite the structures of two chair conformations of 1-tert-butyl-1-methylcyclohexane. Which conformation is more stable?arrow_forwardDoes methylcyclopentane have a stereogenic center?arrow_forward
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- 4. Isomers and Stereocenters ( (a) Assign each set of molecules as constitutional isomers, conformational isomers, enantiomers, diastereomers, or identical. Please write the full name for the type. Molecules Type (b) H₂Ca HgC.. CH3 OCH₂ CH3 af OCH, SP H₂C**** H₂C H₂C NGOCH, H.C_OCKS OCH₂ CH₂ H₁C HC H*** CI H H CI Br H3C CH₂ Br (d) E) (0) For each of the following molecules, write the number of stereocenters and circle the center of any stereocenters. (i) (ii) H₂C (онт (eg 5) (b) -CH3 Isegna CH3 on mots eno H₂C CH3arrow_forwardDraw the stereoisomers of 2-methylcyclohexanol.arrow_forwardBased on the structures of lycopene and β-carotene, which are two chemicals found in another common vegetable, the tomato, answer the following questions: 1. Are they stereoisomers, constitutional isomers or not even isomers? 2. Do you expect them to be relatively polar or nonpolar substances? Why? 3. How many double bonds are in lycopene? How many in β -carotene? 4. As lycopene is transformed into β -carotene, how many pi electrons from the double bonds are transformed into single bonds? How many new single bonds are being formed in β -carotene? 5. The first step of a possible mechanism for the ring closure in the transformation is outlined below (only part of the structure is shown for simplicity). Draw the product that results from this arrow pushing mechanism. Be sure to include any formal charges that arise from the carbon atoms.arrow_forward
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