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

You are watching: When 2-methyl-2-butanol undergoes dehydration in acid, one product is

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) complete each that the adhering to reactions by including the lacking part: one of two people the beginning compound, the necessary reagents and conditions, or the final major product. Present 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) show a sequence of reactions that could be supplied to prepare the target compounds, beginning from the original 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 very same two assets arise, in the same ratio, native acid-catalyzed hydration of one of two people 1,2-dimethylcyclohexene or 1,6-dimethylcyclohexene. Identify the two assets by writing precise structures because that each. Predict which product will be the significant product by referring to the mechanism.


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Both alkenes provide the very same tertiary carbocation upon protonation.

Addition that the nucleophile is desired from the next opposite the surrounding methyl group.


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


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6. (15 points) The anti-Markovnikov addition of HBr come alkenes works as a chain reaction because both propagation procedures are energetically favorable. Compose out the two propagation steps for the in its entirety reaction displayed below. Usage the shortcut dissociation energies shown listed below to calculate ΔH for each step and also for the as whole reaction.

See more: What Are Fungus Like Protists Called, Which Protists Act Like Fungi


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7. (15 points) The conversion of 2-butanol come 2-iodobutane by HI can conceivably go by one SN1 or an SN2 mechanism. Compose a complete mechanism because that each case, mirroring all steps and using electron-pushing arrows. Likewise write clear potential power diagrams because that each case, labeling each action with the matching structure.