Venlafaxine, an antidepressant, was found to be metabolically unstable. The Medicinal Chemistry team then decided to deuterate the methyl hydrogens as shown below, a strategy which successfully delivered a more stable deuterated analogue (see the transformation below). Using your knowledge of reaction kinetics, explain why such a subtle change resulted in a significantly metabolically stable analogue. OH OH CH3 CD3 H₂CO D₂CO Venlafaxine (antidepressant) CH3 CD3 Nonadeuterovenlafaxine (antidepressant)

Venlafaxine, an antidepressant, was found to be metabolically unstable. The Medicinal Chemistry team then decided to deuterate the methyl hydrogens as shown below, a strategy which successfully delivered a more stable deuterated analogue (see the transformation below). Using your knowledge of reaction kinetics, explain why such a subtle change resulted in a significantly metabolically stable analogue. OH OH CH3 CD3 H₂CO D₂CO Venlafaxine (antidepressant) CH3 CD3 Nonadeuterovenlafaxine (antidepressant)

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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5. Using the NMR and IR data, along with the molecular formula, provide structures for compounds A and B, along with the reagents needed to perform the transformation. → Compound A C5H10 NMR: 1.70 ppm, 3H, s 1.82 ppm, 3H, s 2.05 ppm, 3H, d 5.20 ppm, 1H, q IR: 3050 cm¹¹, m 2900 cm¹¹, s 1650 cm¹¹, m Compound B C5H₁1Br NMR: 0.90 ppm, 3H, t 1.75 ppm, 2H, q 1.84 ppm, 6H, s IR: 2950 cm¹¹, s 2900 cm¹¹, s 1450 cm¹, s
What would be a proposed mechanism to get from cyclohexanol to cis-2-methoxycyclohexanol? I know how to get from cyclohexanol to trans-2-methoxycyclohexanol would be to go through acid-catalyzed dehydration via H2SO4, then epoxide ring formation via mCPBA and then alcohol-catalyzed opening, but don't know how to do for the cis version, if possible.
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A C5H8 alkyne is reacted with Lindlar's catalyst and hydrogen gas to yield product with the following H NMR resonances. Provide the structure for Product A and the alkyne 0.78 ppm triplet 3H 1.60 ppm doublet 3H 2.05 ppm doublet of quartets 2H 5.40 ppm doublet of quartets 1H 5.34 ppm doublet of triplets 1H