Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 28.SE, Problem 17MP
The final step in the
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It 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...]
206 Pb
82
Express your answers as integers. Enter your answers separated by a comma.
▸ View Available Hint(s)
VAΣ
ΜΕ ΑΣΦ
Np, N₁ = 82,126
Submit
Previous Answers
?
protons, neutrons
Please draw the inverted chair forms of the products for the two equilibrium reactions
shown below. Circle the equilibrium reaction that would have a AG = 0, i.e., the relative energy of
the reactant (to the left of the equilibrium arrows) equals the relative energy of the product? [No
requirement to show or do calculations.]
CH3
CH3
HH
CH3
1
-CH3
Chapter 28 Solutions
Organic Chemistry
Ch. 28.1 - Draw the full structure of the DNA dinucleotide...Ch. 28.1 - Draw the full structure of the RNA dinucleotide...Ch. 28.2 - What sequence of bases on one strand of DNA is...Ch. 28.4 - Show how uracil can form strong hydrogen bonds to...Ch. 28.4 - What RNA base sequence is complementary to the...Ch. 28.4 - From what DNA base sequence was the following RNA...Ch. 28.5 - List codon sequences for the following amino...Ch. 28.5 - List anticodon sequences on the tRNAs carrying the...Ch. 28.5 - What amino acid sequence is coded by the following...Ch. 28.5 - What is the base sequence in the original DNA...
Ch. 28.7 - Prob. 11PCh. 28.7 - Prob. 12PCh. 28.SE - Identify the following bases, and tell whether...Ch. 28.SE - Identify the following nucleotide, and tell how it...Ch. 28.SE - Amine bases in nucleic acids can react with...Ch. 28.SE - The final step in DNA synthesis is deprotection by...Ch. 28.SE - The final step in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of a...Ch. 28.SE - One of the steps in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of uridine...Ch. 28.SE - Human brain natriuretic peptide (BNP) is a small...Ch. 28.SE - Human and horse insulin both have two polypeptide...Ch. 28.SE - The DNA of sea urchins contains about 32% A. What...Ch. 28.SE - The codon UAA stops protein synthesis. Why does...Ch. 28.SE - Which of the following base sequences would most...Ch. 28.SE - For what amino acids do the following...Ch. 28.SE - Prob. 27APCh. 28.SE - Prob. 28APCh. 28.SE - Draw the complete structure of the ribonucleotide...Ch. 28.SE - Draw the complete structure of the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - Prob. 35APCh. 28.SE - Show the steps involved in a laboratory synthesis...Ch. 28.SE - Draw the structure of cyclic adenosine...Ch. 28.SE - Prob. 38AP
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- 5. Please consider the Newman projection of tartaric acid drawn below as an eclipsed conformer (1). Please draw the most stable conformer and two intermediate energy conformers noting that staggered conformers are lower in energy than eclipsed forms even if the staggered conformers have gauche relationships between groups. [Draw the substituents H and OH on the front carbons and H, OH and CO₂H on the back carbons based on staggered forms. -CO₂H is larger than -OH.] OH COH ICOOH COOH COOH 1 2 COOH COOH 3 4 Staggered Staggered Staggered (most stable) Indicate the number of each conformer above (1, 2, 3 and 4) that corresponds to the relative energies below. Ref=0 Rotation 6. (60 points) a. Are compounds 1 and 2 below enantiomers, diastereomers or identical? OH OH HO HO LOH HO HO OH 2 OH OH b. 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. 3.arrow_forwardThe plutonium isotope with 144 neutrons Enter the chemical symbol of the isotope.arrow_forwardThe mass ratio of sodium to fluorine in sodium fluoride is 1.21:1. A sample of sodium fluoride produced 26.1 gg of sodium upon decomposition. How much fluorine was formed?arrow_forward
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