(2S,3S,5Z)-2-chloro-3-ethyl-2-isobutyl-3-methylhept-5-en-1-ol

(2S,3S,5Z)-2-chloro-3-ethyl-3-methyl-2-(2-methylpropyl)hept-5-en-1-ol

2. (15 points) Write exact structures for the following:

a) a Newmale forecast for the gauche conformer of pentane

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b) the conjugate base of (R)-sec-butyl alcohol

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c) the epoxide of cis-2-hexene

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d) both propagation actions in the chlorination of methane

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e) the rate equation for E2 reaction of t-BuBr via KOH/EtOH

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3. (15 points) Arvariety the complying with in order with respect to the residential property shown. Write “MOST” under the compound via the highest value and “LEAST” under the compound through the lowest value.

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a) heat of combustion

pentane 2-methylpentane 2,2-dimethylbutane

LEAST / / MOST / / MIDDLE

b) number of tertiary carbons

1-chloro-1-methylcyclohexane / 1-chloro-2,2-dimethylcyclohexane / 1-chloro-2,4-dimethylcyclohexane

MIDDLE / / LEAST / / MOST

c) nucleophilicity

KOH KOtBu KSH

MIDDLE / / LEAST / / MOST

d) boiling point

CH3OH CH3Br CH3F

MOST / / MIDDLE / / LEAST

e) retask with Cl2

methylcyclohexane 1-methylcyclohexene 1,1-dimethylcyclohexane

MIDDLE / / MOST / / LEAST

4. (15 points) Complete each of the following reactions by including the absent part: either the original reactant, the important reagents and conditions, or the final significant product.

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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5. (15 points) Complete each of the complying with reactions by adding the absent part: either the original reactant, the important reagents and also conditions, or the last significant product.

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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6. (15 points) Complete each of the adhering to structures by including the lacking substituents on the right side so that the framework is equivalent to the finish structure on the left side.

a)

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b)

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c)

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7. (15 points) Use the table of bond dissociation energies to calculate (delta)H for each of the complying with reactions. Sexactly how the bond energies you usage for your calculations. Use kcal/mol.

a)

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b)

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c)

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8. (20 points) (R,R)-1-bromo-1,3-dimethylcyclopentane undergoes both SN1 solvolysis and also E1 elimicountry upon heating in ethanol.Solvolysis provides 2 diastereomeric assets and also elimicountry provides three constitutional isomers.Write a finish device that reflects all the steps leading to every one of these commodities, especially reflecting the stereochemisattempt at each action. Electron-pushing arrows are optional.

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9. (15 points) Show a sequence of reactions that might be used to synthedimension the adhering to compounds. You might usage acetylene and any alkane through 4 or fewer carbons as the only source of the carbons in your last product. No mechanisms necessary.

a)

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b)

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c)

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10. (15 points) In the presence of acid such as H2SO4, 3,4-dimethyl-1-pentene undergoes isomerization to 2,3-dimethyl-2-pentene. Write a finish device, mirroring all measures and utilizing electron-pushing arrows.

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11. (15 points) Predict the assets that would certainly outcome from complimentary radical monochloricountry of 1,1-dimethylcyclobutane. Predict the intended ratio of the various products, assuming the selectivity of Cl for C-H bonds is on the order 3° > 2° > 1° in the proportion 5 : 4 : 1 .On the structures of the assets, put * at eincredibly chirality facility.

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12. (20 points) Write Newmale projections for the 3 staggered conformations of (R)-2-bromobutane, looking dvery own the C2-C3 bond. Predict which of these conformations can cause E2 elimination through a solid base, including the particular products formed from each conformation. Which would you expect to be the significant E2 elimicountry product and also why?

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Trans is the major product. It is the even more steady product and also it comes from the even more secure condevelopment.