Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305082144
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 55AP
myo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.
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Chapter 4 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- SH 0arrow_forward2. Please consider the two all 'cis' isomers of trimethylcyclohexane drawn below. Draw the two chair conformers of each stereoisomer below (1 and 2) and calculate their torsional interaction energies in order to identify the lower energy conformer for each stereoisomer. Based on your calculations, state which of the two stereoisomers 1 and 2 is less stable and which is more stable. [1,3-diaxial CH3 CH3 = 3.7kcal/mol; 1,3-diaxial CH3 H = 0.88kcal/mol; cis-1,2 (axial:equatorial) CH3 CH3 = 0.88kcal/mol; trans-1,2-diequatorial CH3 CH3 = 0.88kcal/mol) all-cis-1,2,3- 1 all-cis-1,2,4- 2arrow_forwardNonearrow_forward
- What is the mechanism by which the 1,4 product is created? Please draw it by hand with arrows and stuff.arrow_forwardWhat is the relationship between A and B? H3C A Br Cl H3C B Br relationship (check all that apply) O same molecule O enantiomer O diastereomer structural isomer O stereoisomer isomer O need more information to decide O same molecule ☐ enantiomer Br Br Br CH3 Br CI CH3 O diastereomer ☐ structural isomer ☐ stereoisomer isomer O need more information to decide O same molecule O enantiomer Odiastereomer structural isomer O stereoisomer ☐ isomer O need more information to decidearrow_forwardb. Please complete the zig-zag conformation of the compound (3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes. 4arrow_forward
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- Describe the principle of resonance and give a set of Lewis Structures to illustrate your explanation.arrow_forwardDon't used hand raitingarrow_forwardIt is not unexpected that the methoxyl substituent on a cyclohexane ring prefers to adopt the equatorial conformation. OMe H A G₂ = +0.6 kcal/mol OMe What is unexpected is that the closely related 2-methoxytetrahydropyran prefers the axial conformation: H H OMe OMe A Gp=-0.6 kcal/mol Methoxy: CH3O group Please be specific and clearly write the reason why this is observed. This effect that provides stabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way of example, the staggered conformer of ethane is more stable than eclipsed owing to bonding MO interacting with anti-bonding MO...]arrow_forward
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