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Chapter 6: An Overview of Organic Reactions

Q20E

Page 181

Draw an energy diagram for a one-step reaction with Keq<1. Label the parts of the diagram corresponding to reactants, products, transition state, Δ³Òo, andΔ³Ò# . IsΔ³Òo positive or negative?

Q21E

Page 181

Draw an energy diagram for a two-step reaction withKeq > 1. Label the overall Δ³Òo, transition states, and intermediate. IsΔ³Òo positive or negative?

Q22E

Page 181

Draw an energy diagram for a two-step exergonic reaction whose second step is faster than its first step.

Q23E

Page 181

Draw an energy diagram for a reaction with Keq=1 . What is the value of Δ³Òo in this reaction?

Q24E

Page 181

The addition of water to ethylene to yield ethanol has the following thermodynamic parameters:

(a) Is the reaction exothermic or endothermic?

(b) Is the reaction favorable (spontaneous) or unfavorable (nonspontaneous) at room temperature (298 K)?

Q25E

Page 181

When isopropylidenecyclohexane is treated with strong acid at room

temperature, isomerization occurs by the mechanism shown below to yield 1-isopropylcyclohexene:

At equilibrium, the product mixture contains about 30% isopropylidene- cyclohexane and about 70% 1-isopropylcyclohexene.

(a)What is an approximate value of Keq for the reaction?

(b)Since the reaction occurs slowly at room temperature, what is its approximate∆G‡?

(c)Draw an energy diagram for the reaction.

Q27E

Page 181

Draw the electron-pushing mechanism for each radical reaction below. Identify each step as initiation, propagation, or termination.

(a)

b)

c)

Q28E

Page 181

Draw the complete mechanism for each polar reaction below.

(a)

(b)

(c)

Q38E

Page 149

Despite the limitations of radical chlorination of alkanes, the reaction is still useful for synthesizing certain halogenated compounds. For which of the following compounds does radical chlorination give a single monochloro product?

Q39E

Page 149

Draw all of the different monochlorinated products one would obtain by the radical chlorination of these compounds. (Do not consider the stereochemistry of the products in your answer.)

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