1. (15 points) Write finish names because that each that the following, consisting of stereochemistry if that is especially shown.

You are watching: 2-methyl-2-butanol dehydration

a)

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(2E,5Z)-6-chloro-3-methyl-2,5-octadien-4-ol

b)

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trans-4-vinylcyclohexanol

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trans-4-ethenylcyclohexanol

c)

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5,5-dimethyl-6-hepten-1,4-diol

2. (15 points) finish each of the adhering to reactions by adding the missing part: one of two people the beginning compound, the essential reagents and conditions, or the final significant product. Show stereochemistry if the is specific.

a)

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b)

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c)

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d)

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e)

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3. (15 points) present a sequence of reactions that could be supplied to prepare the target compounds, starting from the initial compound.

a) 3-ethyl-2-pentene, starting from 3-ethylpentane


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b)

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c)

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4. (15 points) The exact same two assets arise, in the same ratio, from acid-catalyzed hydration of one of two people 1,2-dimethylcyclohexene or 1,6-dimethylcyclohexene. Recognize the two assets by writing exact structures for each. Predict which product will certainly be the major product by introduce to the mechanism.


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Both alkenes provide the very same tertiary carbocation top top protonation.

Addition the the nucleophile is preferred from the side opposite the adjacent methyl group.


5. (10 points) compose a complete mechanism for the dehydration the 3-methyl-2-butanol using hot aqueous sulfuric acid. Present all steps and use electron-pushing arrows. Show the pathways to all likely products.


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6. (15 points) The anti-Markovnikov enhancement of HBr come alkenes works as a chain reaction since both propagation actions are energetically favorable. Write out the 2 propagation procedures for the as whole reaction displayed below. Use the shortcut dissociation energies shown below to calculation ΔH for each step and also for the all at once reaction.

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7. (15 points) The counter of 2-butanol to 2-iodobutane by HI can conceivably go by one SN1 or an SN2 mechanism. Write a complete mechanism because that each case, reflecting all steps and using electron-pushing arrows. Additionally write clean potential power diagrams for each case, labeling each action with the corresponding structure.