Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 14, Problem 45P
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Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a ve-membered ring.
Draw the most stable product formed in each of the reactions shown.
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Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.
Chapter 14 Solutions
Organic Chemistry (6th Edition)
Ch. 14.1 - Prob. 2PCh. 14.2 - Problem 16.3 Draw a second resonance structure for...Ch. 14.2 - Prob. 4PCh. 14.2 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 14.3 - Prob. 6PCh. 14.4 - Prob. 7PCh. 14.4 - Prob. 8PCh. 14.8 - Problem 16.12 Using hybridization, predict how the...Ch. 14.8 - Problem 16.13 Use resonance theory to explain why...Ch. 14.9 - Prob. 15P
Ch. 14.9 - Prob. 16PCh. 14.10 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 14.11 - Prob. 19PCh. 14.12 - Problem 16.19 Draw the product formed when each...Ch. 14 - Prob. 32PCh. 14 - 16.31 Which of the following systems are...Ch. 14 - 16.32 Draw all reasonable resonance structures for...Ch. 14 - Prob. 35PCh. 14 - 16.35 Explain why the cyclopentadienide anion A...Ch. 14 - Prob. 38PCh. 14 - 16.37 Draw the structure of each compound.
a. in...Ch. 14 - 16.41 Draw the products formed when each compound...Ch. 14 - Prob. 44PCh. 14 - 16.43 Treatment of alkenes A and B with gives the...Ch. 14 - 16.44 Draw a stepwise mechanism for the following...Ch. 14 - Prob. 47PCh. 14 - 16.57 A transannular Diels–Alder reaction is an...Ch. 14 - Draw a stepwise mechanism for the following...Ch. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - 16.65 The treatment of isoprene with one...
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- (a) Add curved arrows for each step to show how A is converted to the epoxy ketone C. (b) Classify the conversion of A to C as a substitution, elimination, or addition. (c) Draw one additional resonance structure for B.arrow_forward5) Draw the enols available to compounds A-D. Explain why A is 100% enolized but B, C, and D are 100% ketone. B Darrow_forwardAddition of water to an alkyne gives a keto‑enol tautomer product. Draw the ketone that is in equilibrium with the given enol.arrow_forward
- • Draw the curved arrow mechanism for the following reaction. o Show all electrons, spectator ions, formal charges, and intermediates. o Only account for the products shown. • Account for any stereochemistry and regiochemistry provided. Overall Reaction 1. 1 equiv CH₂MgBr, ether 2 water workup OH + enantiomerarrow_forward1. (a) Propose structure of the major product when A is reacted with dil. H2SO4. (b) Propose a mechanism for the reaction. Show all intermediate structures and all electron flow with arrows. OH dil. H2SO4arrow_forwardDraw a stepwise, detailed mechanism for the following reaction. + CH;NH2 N-CH3 CH,NH, Cr- (excess)arrow_forward
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