Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 16, Problem 16.43P
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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 16 Solutions
Organic Chemistry
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Problem 16.3 Draw a second resonance structure for...Ch. 16 - Prob. 16.4PCh. 16 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Problem 16.9 Determine the hybridization of the...Ch. 16 - Problem 16.10 Draw the structure consistent with...
Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75P
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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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