Chapter 11, Problem 58P

Problems: 1. Suggest a synthesis of amine (20), needed to study 135 whether cyclisation would occur during bromination of the double bond. NH2 (20)

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Show the full mechanism of how the molecule ((1E, 3E, 5E)-1-methoxyhepta-1,3,5-triene) is built using substitution and elimination reactions. You can start with an alkane of any carbon length with any number of leaving groups attached or with a alkoxide of any carbon length (conjugate base of an alcohol). Show each step and and explanation for each reaction. Also include why the reagents and solvents were picked and what other products can be expected.

Problems 1. Acids (11) and (12) were both made by Grignard addition to CO2 rather than by cyanide displacement (p T 80). Why? (11) -CO2H MeO- (12) CO,H

2. Aldehyde (8) was needed for a butenolide synthesis. How would (8) be made? CHO

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6. Consider the following exothermic reaction below. 2Cu2+(aq) +41 (aq)2Cul(s) + 12(aq) a. If Cul is added, there will be a shift left/shift right/no shift (circle one). b. If Cu2+ is added, there will be a shift left/shift right/no shift (circle one). c. If a solution of AgNO3 is added, there will be a shift left/shift right/no shift (circle one). d. If the solvent hexane (C6H14) is added, there will be a shift left/shift right/no shift (circle one). Hint: one of the reaction species is more soluble in hexane than in water. e. If the reaction is cooled, there will be a shift left/shift right/no shift (circle one). f. Which of the changes above will change the equilibrium constant, K?

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