1. (15 points) Write complete names for each the the following, consisting of stereochemistry if the is especially shown.

You are watching: Dehydration of 3-methyl-2-pentanol

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 adding the absent part: one of two people the beginning compound, the crucial reagents and also 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) display a sequence of reactions that could be offered to prepare the target compounds, starting from the initial compound.

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


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b)

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c)

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4. (15 points) The very same two commodities arise, in the very same ratio, indigenous acid-catalyzed hydration of one of two people 1,2-dimethylcyclohexene or 1,6-dimethylcyclohexene. Determine the two assets by writing precise structures because that each. Predict i beg your pardon product will be the major product by referring to the mechanism.


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Both alkenes provide the very same tertiary carbocation ~ above protonation.

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


5. (10 points) write a finish mechanism because that the dehydration the 3-methyl-2-butanol using warm aqueous sulfuric acid. Show all steps and also use electron-pushing arrows. Show the pathways to all likely products.


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6. (15 points) The anti-Markovnikov addition of HBr to alkenes functions as a chain reaction since both propagation actions are energetically favorable. Create out the 2 propagation procedures for the in its entirety reaction shown below. Use the shortcut dissociation energies shown below to calculation ΔH because that each step and also for the all at once reaction.

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7. (15 points) The counter of 2-butanol come 2-iodobutane by HI might conceivably walk by an SN1 or one SN2 mechanism. Write a finish mechanism because that each case, mirroring all steps and also using electron-pushing arrows. Also write clear potential energy diagrams for each case, labeling each action with the matching structure.