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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Chapter 25 Solutions
Organic Chemistry (8th Edition)
Ch. 25.1 - Prob. 1PCh. 25.3 - Which has a higher melting point, glyceryl...Ch. 25.3 - Draw the structure of an optically inactive fat...Ch. 25.3 - Draw the structure of an optically active fat...Ch. 25.5 - Do the identities of R1 and R2 in phosphatidic...Ch. 25.5 - Membranes contain proteins, Integral membrane...Ch. 25.5 - Prob. 8PCh. 25.5 - The membrane phospholipids in deer have a higher...Ch. 25.6 - Treating PGC2 with a strong base such as sodium...Ch. 25.7 - Mark off the isoprene units in menthol, -selinene,...
Ch. 25.7 - Prob. 13PCh. 25.7 - Prob. 14PCh. 25.8 - Propose mechanisms for the Claisen condensation...Ch. 25.8 - Prob. 16PCh. 25.8 - Propose a mechanism for the conversion of...Ch. 25.8 - Propose a mechanism for the biosynthesis of...Ch. 25.8 - Propose a mechanism for the conversion of the E...Ch. 25.8 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.8 - Prob. 22PCh. 25.8 - Prob. 23PCh. 25.9 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25.10 - Prob. 26PCh. 25.10 - Prob. 27PCh. 25.10 - The acid component of a cholesterol ester is a...Ch. 25.10 - Prob. 29PCh. 25.10 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - An optically active fat, when completely...Ch. 25 - Prob. 33PCh. 25 - a. How many different triacylglycerols are there...Ch. 25 - Cardiolipins are found in heart muscles. Draw the...Ch. 25 - Nutmeg contains a simple, fully saturated...Ch. 25 - Draw the product that is obtained from the...Ch. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - 5-Androstene-3.17-dione is isomerized to...Ch. 25 - Prob. 44PCh. 25 - Eudesmol is a sesquiterpene found in eucalyptus....Ch. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Diethylstilbestrol (DES) was given to pregnant...
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- looking at this reaction (first image), The second image shows the 13C NMR spectrum of the 2-acetnaphthone which is the starting material and an 13C NMR spectrum obtained for the reaction product: Based a comparison of the two 13C NMR spectra, is product A or product B the major product of the reaction? - Explain your reasoning.arrow_forwardBased on this HNMR of Acetylferrocene, explain why the hydrogens labeled are equivalent, why the splitting pattern appears the way it does on the HNMR, and why the chemical shift of each signal appears in that order?arrow_forwardHow can 1H NMR be used to prove that the addition of HBr to propene follows the rule that says that the electrophile adds to the sp2 carbon bonded to the most hydrogens?arrow_forward
- Assign the peaks in your IR spectra for the peaks above 1400 cm-1. (IR spectra of the product of Pinacol Rearrangement, Pinacolone).arrow_forwardAttached is the NMR of 1-indanone (top), 3,4 dimethoxybenzaldehyde (middle), and the product of the reaction (bottom). Based on the spectra, did the reaction work to obtain a pure, final condensation product? How do you know?arrow_forwardExplain why the cyclopentadienide anion A gives only one signal in its13C NMR spectrumarrow_forward
- Explain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downeld in the 13C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, while the α carbon absorbs at 122.5 ppm.arrow_forwardExplain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downfield in the 13C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, whereas the α carbon absorbs at 122.5 ppm.arrow_forwardExplain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downfield in the 13 C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, while the α carbon absorbs at 122.5 ppm.arrow_forward
- What product did you obtain from the competitive nitration of methyl benzoate? a. Which particular IR absorptions led you to this conclusion? b. How can the NMR signals in the aromatic region be used to confirm the identity of your product?arrow_forward6. Draw the product of the following reaction. How many signals in the 13C and 1H NMR would you expect?arrow_forwardWriting down all the relevant resonant structures and that of the resonance hybrid, propose a mechanism that explains the reason why methyl benzoate is nitrated in the meta position.arrow_forward
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