Question 1

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Accepted Answer

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Question 2

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

Accepted Answer

The likelihood of rearrangement in an SN1 reaction is dependent on the stability of the carbocation intermediate. In this case, the 2-chloro-3,3-dimethylpentane can undergo rearrangement to form a more stable carbocation intermediate, which would increase the speed of the reaction. The other options do not have highly unstable carbocation intermediates and are less likely to undergo rearrangement.

Question 3

Why does CH₂=CHCHBrCH₃ undergo solvolysis much more rapidly than 2-bromobutane?

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Question 4

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

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Question 5

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

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Question 6

What is Zaitsev's rule?

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Question 7

Provide the structure of the major organic product which results in the following reaction.

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Question 8

A sample of 1-chloro-1-phenylethane with an [α]²⁵_D of -94.8^∘ is reacted with NH₃ in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [α]²⁵_D of -8.6^∘. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0^∘ and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3^∘, which of the following statements best describes this reaction?

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Question 9

Provide $\underline{\text{ two }}$  circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

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Question 10

Predict the structure of the expected product for the following reaction.

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Question 11

Which of the cations below would be subject to a structural rearrangement?

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Question 12

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

Accepted Answer

In solvolysis reactions, the carbocation intermediate formed can undergo rearrangement to form a more stable carbocation. The more substituted the carbocation is, the more stable it is, and therefore the more likely it is to undergo rearrangement. Option C (2-chloro-2-methylpentane) has a primary carbocation intermediate which is the least stable, therefore this compound is least likely to undergo rearrangement. The other options have secondary or tertiary carbocation intermediates and are more likely to undergo rearrangement.

Question 13

When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

Accepted Answer

Ionization at a single stereocenter of a chiral compound results in a planar carbocation, which is achiral due to its symmetry.

Question 14

S_N1 reactions usually proceed with:

Accepted Answer

S_N1 reactions usually exhibit a slight preference for inversion over retention at the center undergoing substitution. This is due to the mechanism of the reaction, which involves the attack of the nucleophile on the opposite side of the leaving group, leading to inversion of configuration. However, some degree of retention may also occur due to competing mechanisms or other factors. Therefore, the best choice is B, which reflects this overall trend but also acknowledges the possibility of some retention.

Question 15

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

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Question 16

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

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Question 17

Provide the structure of the major organic products which result in the reaction below.

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Question 18

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

Accepted Answer

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Question 19

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Accepted Answer

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Question 20

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)? 
I. Rate = k[base]
II. Rate = k[base][RX]
III. Rate = k[RX]
IV. The reactions occur in two or more distinct steps.
V. Rearrangements are sometimes seen.

Accepted Answer

E1 reactions of alkyl halides involve a rate-determining step that only depends on the concentration of the alkyl halide ([RX]), hence the rate = k[RX]. They occur in multiple steps, often starting with the formation of a carbocation intermediate, which can lead to rearrangements.

Quiz 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

Why does CH₂=CHCHBrCH₃ undergo solvolysis much more rapidly than 2-bromobutane?

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

What is Zaitsev's rule?

Provide the structure of the major organic product which results in the following reaction.

Provide $\underline{\text{ two }}$ circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

Predict the structure of the expected product for the following reaction.

Which of the cations below would be subject to a structural rearrangement?

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

S_N1 reactions usually proceed with:

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

Provide the structure of the major organic products which result in the reaction below.

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX) ? I. Rate = k[base] II. Rate = k[base][RX] III. Rate = k[RX] IV. The reactions occur in two or more distinct steps. V. Rearrangements are sometimes seen.

Quiz 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Which of the following alkyl halides is most likely to undergo rearrangement in an SN1 reaction?

Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane?

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

What is Zaitsev's rule?

Provide the structure of the major organic product which results in the following reaction.

Provide two ‾\underline{\text{ two }} two ​ circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

Predict the structure of the expected product for the following reaction.

Which of the cations below would be subject to a structural rearrangement?

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

SN1 reactions usually proceed with:

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

Provide the structure of the major organic products which result in the reaction below.

Dehydration of 1-butanol with concentrated sulfuric acid at 140∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX) ? I. Rate = k[base] II. Rate = k[base][RX] III. Rate = k[RX] IV. The reactions occur in two or more distinct steps. V. Rearrangements are sometimes seen.

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

Why does CH₂=CHCHBrCH₃ undergo solvolysis much more rapidly than 2-bromobutane?

Provide $\underline{\text{ two }}$ circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

S_N1 reactions usually proceed with:

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?