Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 25.9, Problem 25P

Draw the individual 1,2-hydride and 1,2-methyl shifts responsible for conversion of the protosterol cation to lanosterol. How many hydride shifts are involved? How many methyl shifts?

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Draw the two intermediates, including resonance structures, for the attack of nitronium ion on pyrrole. Which position is favored? Why?
2. (9 points total) Each of the following Grignard reagents undergo reaction with CO₂ (solid). Grignard reagents: Number of ¹H NMR signals in the reaction product: CI A MgBr MeO B MgBr OMe MgBr Me MgCl a. (8 points) How many ¹H NMR signals do you expect to see in the spectrum of each product? Assume that the products are pure and that the carboxylic acid peak is present. Please write directly in the boxes. b. (1 point) Which Grignard reagent (A, B, C, or D) will lead to the product with the fewest ¹3C NMR signals?
Draw the three intermediates, including resonance structures, for the attack of nitronium ion on pyridine. Which position(s) is favored? Why?

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Organic Chemistry (8th Edition)

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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY