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Classify states 2–4 in the potential energy diagram.

A. 2, 3, and 4 are transition states

B. 2, 3, and 4 are reactive intermediates

C. 2 and 4 are transition states; 3 is a reactive intermediate

D. 2 and 4 are reactive intermediates; 3 is a transition state 

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Classify the elementary steps in the mechanism according to their molecularity.

A. Step 1 is unimolecular; step 2 is bimolecular.

B. Step 1 is bimolecular; step 2 is unimolecular.

C. Both steps are unimolecular.

D. Both steps are bimolecular. 

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Of two possible structures A and B for the conjugate acid of guanidine, the more stable is the one that is better stabilized by electron delocalization. Which one is it? 

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Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

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Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

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Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

 

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Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

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Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

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Write an equation for the Brønsted–Lowry acid–base reaction that occurs when each of the following bases reacts with water. Show all unshared electron pairs and formal charges, and use curved arrows to track electron movement. 

 

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By applying Hammond’s postulate to the potential energy diagram for this reaction, we can say that:

A. the structure of 2 is more carbocation-like than 4

B. the structure of 2 is less carbocation-like than 4

C. the structure of 2 resembles 1 more than it resembles 3

D. the structure of 4 resembles 5 more than it resembles 3 

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What best describes the species at the rate-determining transition state? 

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According to the potential energy diagram, the overall reaction is:

A. endothermic

B. exothermic

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Ethanol is: 

A. a catalyst

B. a reactive intermediate

C. a Brønsted acid

D. a Brønsted base 

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Although useful in agriculture as a soil fumigant, methyl bromide is an ozone-depleting chemical, and its production is being phased out. The industrial preparation of methyl bromide is from methanol, by reaction with hydrogen bromide. Write a mechanism for this reaction and classify it as SN1 or SN2. 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.

 (g) 1-Cyclopentylethanol or 1-ethylcyclopentanol 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.

(f) 1-Methylcyclopentanol or trans -2-methylcyclopentanol 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.

 (e) 1-Methylcyclopentanol or cyclohexanol 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.

 (d) 2-Methylbutane or 2-butanol

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. 

(c) 2-Methyl-2-butanol or 2-butanol 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. 

(b) 2-Methyl-1-butanol or 2-butanol 

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Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. 

(a) 1-Butanol or 2-butanol 

 

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Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction. 

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Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction. 

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Write a chemical equation for the reaction of 1-butanol with each of the following: 

(d) Phosphorus tribromide

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Write a chemical equation for the reaction of 1-butanol with each of the following: 

 (c) Sodium bromide, sulfuric acid, heat

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