Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 11.12, Problem 19P
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2,3-Di-tert-butyl-1,3-butadiene is extremely unreactive in Diels–Alder reactions. Explain.
Which constitutional isomer represents the product of this Diels-Alder reaction?
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Chapter 11 Solutions
Organic Chemistry - Standalone book
Ch. 11.1 - Prob. 1PCh. 11.1 - Prob. 2PCh. 11.2 - The two compounds shown differ by a factor of 60...Ch. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.2 - Prob. 6PCh. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Evaluate 2,3,3-trimethyl-1-butene as a candidate...Ch. 11.4 - After heating a solution of allyl tert-butyl...
Ch. 11.5 - Prob. 11PCh. 11.6 - Prob. 12PCh. 11.8 - Prob. 13PCh. 11.9 - What dienes containing isolated double bonds are...Ch. 11.10 - Prob. 15PCh. 11.10 - Prob. 16PCh. 11.11 - Prob. 17PCh. 11.12 - Dicarbonyl compounds such as quinones are reactive...Ch. 11.12 - 2,3-Di-tert-butyl-1,3-butadiene is extremely...Ch. 11.12 - Methyl acrylate (H2C=CHCO2CH3) reacts with...Ch. 11.13 - Prob. 21PCh. 11.14 - What diene and dienophile could you use to prepare...Ch. 11.14 - Write equations in the synthetic direction for the...Ch. 11.16 - Prob. 24PCh. 11.16 - Prob. 25PCh. 11 - Write structural formulas for each of the...Ch. 11 - Give an acceptable IUPAC name for each of the...Ch. 11 - A certain species of grasshopper secretes an...Ch. 11 - Which of the following are chiral?...Ch. 11 - Describe the molecular geometry expected for...Ch. 11 - Prob. 31PCh. 11 - What compound of molecular formula C6H10 gives...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - Prob. 35PCh. 11 - Prob. 36PCh. 11 - Identify the more reactive dienophile in each of...Ch. 11 - Prob. 38PCh. 11 - Prob. 39PCh. 11 - Prob. 40PCh. 11 - Prob. 41PCh. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Show how to prepare each of the following...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Compound A was converted to compound B by the...Ch. 11 - Suggest reasonable explanations for each of the...Ch. 11 - Prob. 53PCh. 11 - Prob. 54PCh. 11 - Prob. 55DSPCh. 11 - Prob. 56DSPCh. 11 - Prob. 57DSPCh. 11 - Prob. 58DSPCh. 11 - Prob. 59DSP
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- Complete the Diels-Alder reactions by drawing structures for the products in each question.arrow_forwardBASED ON THIS EXPERIMENT: The purpose of this experiment is to perform a Diels-Alder reaction between E,E-2,4-hexadien-1-ol and maleic anhydride in a "neat" or solventless condition. The Diels-Alder reaction is a [4+2] cycloaddition that forms a six-membered ring, typically a derivative of cyclohexene. The diene, E,E-2,4-hexadien-1-ol, and the dienophile, maleic anhydride, will be mixed and ground together, resulting in a eutectic mixture. The reaction is unique as it occurs without a solvent, contributing to a "greener" experiment. After the reaction, the product will be analyzed through mass measurements, and the mechanism involves a subsequent nucleophilic acyl substitution. QUESTION: how many carbon atoms does a dienophile contribute to the Diels-Alderadduct? How many carbon atoms does a diene contribute? draw andlabel which reagent is the diene, and which is the dienophile.arrow_forwardRank the following dienes in order of their reactivity in standard Diels-Alder reactions (1= most reactive, 4= least reactive). Be sure to briefly explain your choices.arrow_forward
- Explain the stereochemistry of the product of the Diels-Alder reaction shown below:arrow_forwardRank the following dienes from most reactive to least reactive in a Diels–Alder reaction:arrow_forwardOf the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.arrow_forward
- Predict products of each Diels-Alder reaction (including stereochemistry)arrow_forwardWhat is the purpose of A Pericyclic Diels-Alder Reaction ?arrow_forwardWrite the equation and the corresponding mechanisms for the Diels-Alder reactions ofcyclopentadiene with EACH of the following compounds:(a) Vinyl acetate(b) Acrylic acid(c) Dimethyl acetylenedicarboxylatearrow_forward
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