Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 30.8, Problem 8P
Propose a mechanism to account for the fact that heating 1-deuterioindene scrambles the isotope label to all three positions on the five-membered ring:
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Chapter 30 Solutions
Organic Chemistry
Ch. 30.1 - Prob. 1PCh. 30.3 - Prob. 2PCh. 30.3 - Prob. 3PCh. 30.4 - Prob. 4PCh. 30.6 - What stereochemistry would you expect for the...Ch. 30.6 - Prob. 6PCh. 30.7 - Prob. 7PCh. 30.8 - Propose a mechanism to account for the fact that...Ch. 30.8 - When a 2, 6-disubstituted allyl phenyl ether is...Ch. 30.9 - Prob. 10P
Ch. 30.SE - Predict the product obtained when the following...Ch. 30.SE - Prob. 12VCCh. 30.SE - The following rearrangement of N-allyl-N,...Ch. 30.SE - Plastic photochromic sunglasses are based on the...Ch. 30.SE - Prob. 15MPCh. 30.SE - Prob. 16MPCh. 30.SE - Prob. 17MPCh. 30.SE - Prob. 18APCh. 30.SE - Prob. 19APCh. 30.SE - Prob. 20APCh. 30.SE - Prob. 21APCh. 30.SE - Prob. 22APCh. 30.SE - Prob. 23APCh. 30.SE - Prob. 24APCh. 30.SE - Prob. 25APCh. 30.SE - Prob. 26APCh. 30.SE - Prob. 27APCh. 30.SE - Prob. 28APCh. 30.SE - Propose a pericyclic mechanism to account for the...Ch. 30.SE - Prob. 30APCh. 30.SE - Prob. 31APCh. 30.SE - Prob. 32APCh. 30.SE - Prob. 33APCh. 30.SE - Bicyclohexadiene, also known as Dewar benzene, is...Ch. 30.SE - Prob. 35APCh. 30.SE - Prob. 36APCh. 30.SE - The 1H NMR spectrum of bullvalene at 100 C...Ch. 30.SE - Prob. 38APCh. 30.SE - Prob. 39APCh. 30.SE - Prob. 40APCh. 30.SE - In light of your answer to Problem 30-40, explain...
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- How many alkenes yield 2,3−dimethylbutane on catalytic hydrogenation?arrow_forwardThe central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other. Draw the two enantiomers of penta-2,3-diene. A model may be helpful.arrow_forwardConsider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Deduce the mechanism of this reaction working step by step. Write all possible products showing the stereochemistry.arrow_forward
- What is the mechanism for the reaction NaNH2 and cyclopentadiene?arrow_forwardDraw the possible products resulting from addition of 1 equivalent of HCl to 1-phenyl-1,3-butadiene. Which would you expect to predomi- nate, and why?arrow_forwardWhen Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.Show why A predominates at -15 °C and B predominates at 60 °C.arrow_forward
- Given the final product and reagents for each step in the forward synthesis of this cyclohexane-containing internal alkyne, please propose the structures for the synthetic intermediates A-E below.arrow_forwardAlthough there are nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane, one stereoisomer reacts 7000 times more slowly than any of the others in an E2 elimination. Draw the structure of this isomer and explain why this is so.arrow_forwardWhen Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.(a) Propose structures for products A and B. (Hint: In many cases, an allylic carbocationis more stable than a bromonium ion.)arrow_forward
- Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.arrow_forwardBased on what you know about the relative stabilities of alkyl radicals and benzylicradicals, predict the product of addition of HBr to 1-phenylpropene in the presence ofa free-radical initiatorarrow_forwardwhen 5-iodo-1,3-cyclopentadiene was refluxed in neat methanol, even extended reaction times did not produce any product and the unomodified starting material was recovered, explain whyarrow_forward
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