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Each of the following carbocations has the potential to rearrange to a more stable one. Write the structure of the rearranged carbocation, and use curved arrows to show how it is formed. 

 

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Each of the following carbocations has the potential to rearrange to a more stable one. Write the structure of the rearranged carbocation, and use curved arrows to show how it is formed.

 

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In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?

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You have available 2,2-dimethylcyclopentanol (A) and 2-bromo-1,1-dimethylcyclopentane (B) and wish to prepare 3,3-dimethylcyclopentene (C). Which would you choose as the more suitable reactant, A or B, and with what would you treat it? 

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Menthyl chloride and neomenthyl chloride have the structures shown. One of these stereoisomers undergoes elimination on treatment with sodium ethoxide in ethanol much more readily than the other. Which reacts faster, menthyl chloride or neomenthyl  chloride? Why?

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The rate of the reaction

(CH3)3 CCl + NaSCH2CH3 → (CH3)2C=CH2 + CH3CH2SH + NaCl

is first-order in (CH3)3CCl and first-order in NaSCH2CH3 . Give the symbol (E1 or E2) for the most reasonable mechanism, and use curved arrows to show the flow  of electrons.  

 

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter. 

 

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter. 

 

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Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter.
 

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Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.
 

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Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.
 

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Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.
 

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Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.
 

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Choose the compound of molecular formula C 7H13Br that gives each alkene shown as the exclusive product of E2 elimination.

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Choose the compound of molecular formula C 7H13Br that gives each alkene shown as the exclusive product of E2 elimination.
 

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Choose the compound of molecular formula C 7H13Br that gives each alkene shown as the exclusive product of E2 elimination.
 

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Choose the compound of molecular formula C7H13Br that gives each alkene shown as the exclusive product of E2 elimination.
 

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Choose the compound of molecular formula C 7H13Br that gives each alkene shown as the exclusive product of E2 elimination.
 

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Choose the compound of molecular formula C 7H13Br that gives each alkene shown as the exclusive product of E2 elimination.
 

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