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

You are watching: (s)-2-chloropentane and nash

a)

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(2E,4S,6Z)-4-chloro-2,6-octadien-1-ol

b)

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(1S,3S)-3-bromo-3-chloro-1-methylcyclohexanol

c)

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(3R,4S)-4-chloro-5-methyl-1-hexen-3-ol

2. (15 points) Arrange every of the complying with in order through respect come the building indicated. Compose “MOST” under the compound through the greatest value and “LEAST” under the compound with the lowest value ( or “EQUAL” if appropriate).

a) nucleophilicity


H2O / NaOH / NaSH

LEAST / center / MOST


b) nucleophilicity


NaI / NaBr / I2

MOST / middle / LEAST


c) optical rotation (absolute value)


(R)-2-chloropentane / (S)-2-chloropentane / racemic-2-chloropentane

EQUAL / same / LEAST


d) price of hydrolysis in neutral water


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LEAST / middle / MOST


e) rate of reaction through NaN3 in DMSO


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LEAST / center / MOST


3. (15 points) complete each that the complying with reactions by adding the absent part: either the beginning compound, the necessary reagents and conditions, or the final significant product. Display stereochemistry if the is specific.

a)

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b)

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c)

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d&e)

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4a. (10 points) finish the reaction presented below, initially ignoring stereochemistry.


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If the initial compound is the (R) stereoisomer, the product is meant to be:


(R) / (S) / racemic/ can’t tell/ other

If the original compound has actually an optical rotation the is (+), the product is supposed to be:


(+) / (-) / optically inactive/ can’t tell/ other

4b. (10 points) complete the reaction presented below, originally ignoring stereochemistry.


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If the original compound is the (R) stereoisomer, the product is expected to be:


(R) / (S) / racemic/ can’t tell/ other

If the original compound has an optical rotation that is (+), the product is meant to be:


(+) / (-) / optically inactive/ can’t tell/ other

5. (15 points) research the bag of structures below and also identify their relationship to one another, utilizing the letter codes below:


A - the the same structure B - constitution isomers C - conformational isomers D - diastereomers E - enantiomers F - no one of the above

a)

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D

b)

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D

c)

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B

d)

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E

e)

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E


6a. (12 points) compose a complete mechanism because that the solvolysis (substitution only) reaction presented below. Present all steps and electron pushing arrows. Carry out not consider any rearrangements.

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6b. (8 points) In order to assist relieve the ring strain, a cation rearrangement deserve to occur. Write a clean electron-pushing system that illustrates exactly how a bigger ring may be formed and show the final product that would result.