Chem 1120 Quiz 3

Instructions: This quiz is open-book. You may use any book, magazine, or other printed or web-based materials you feel are helpful. You may discuss this quiz with other members of this immediate class and section. You may not discuss, receive help on, or work on this quiz with tutors, friends, family members, or any one outside of class without my explicit permission. Violation of this stipulation is academic misconduct and is grounds for dismissal from class. You must work the quiz in its entirety by yourself before meeting in groups to compile a group quiz. I will award extra credit (5 pts) to those who work in groups of 2-5 and who submit a group quiz. You must show all your work for full credit, or to receive partial credit if you make a mistake.

(4 pts) Show the complete pathway for the reaction of aniline with chlorine in the presence of ferric chloride (iron (III) chloride). Identify the Lewis acids and bases, draw the structures of all organic products, and correctly name them.
(9 pts) Identify and provide structures and IUPAC names for all of the 17 isomeric alcohols with the molecular formula C₆H₁₄O. Neatly draw, label, and number your work or you will not receive credit.
(4 pts) The addition of sodium dichromate to an unknown organic liquid resulted in the formation of 2-hydroxy-3-keto-2-methylbutanoic acid (note: a keto group is a carbonyl group). Give the structure and name of the original compound.
(4 pts) A student mixed 2-methyl-1-butanol with sulfuric acid and heated the mixture to 200°C. After the first reaction was completed the student collected and mixed the product(s) with hydrochloric acid in a second reaction. What was the result? Show the structures and names of the reactants and products of both reactions.
(4 pts) In which reaction is more oxygen consumed, the combustion of 0.65 moles of 2-methoxy-2-butanol or the combustion of 0.55 moles of 3-methyl-1,2-cyclopentanediol? Show balanced equations for each reaction and the calculations used to support your answer.