Question 1

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

Accepted Answer

The answer of Provide the structure of the major organic...

Question 2

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.

Accepted Answer

The answer of When t-butyl chloride undergoes solvolysis in a...

Question 3

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

Accepted Answer

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Question 4

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

Accepted Answer

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Question 5

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

Accepted Answer

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Question 6

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.

Accepted Answer

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Question 7

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

Accepted Answer

The least likely to undergo rearrangement during solvolysis is the alkyl chloride with a tertiary carbon, so choice C (2-chloro-2-methylpentane) is the best choice. The other options have secondary or cyclohexyl carbons, which are more likely to undergo rearrangement during the reaction.

Question 8

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

Accepted Answer

The reaction is an SN2 reaction, which proceeds with inversion of configuration. The product mixture is therefore a mixture of diasteromeric ethers.

Question 9

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

Accepted Answer

Rearrangement in SN1 reactions occurs when there is a carbocation intermediate formed. In this case, the alkyl halide with the most stable carbocation intermediate will be the one most likely to undergo rearrangement. The most stable carbocation is the tertiary carbocation, followed by secondary, and then primary. Among the given options, 2-chloro-3,3-dimethylpentane has a tertiary carbon adjacent to the leaving group, making it the most likely to undergo rearrangement.

Question 10

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

Accepted Answer

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Question 11

Provide two circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

Accepted Answer

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Question 12

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

Accepted Answer

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Question 13

S_N1 reactions usually proceed with ________.

Accepted Answer

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Question 14

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?

Accepted Answer

The answer of A sample of 1-chloro-1-phenylethane with an [α]²⁵_D...

Question 15

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 16

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 17

When a S_N1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

Accepted Answer

In an S_N1 reaction, the formation of a carbocation intermediate leads to a racemic mixture due to the planar nature of the carbocation, allowing nucleophilic attack from either side.

Question 18

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.

Question 19

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

The dehydration of 1-butanol with concentrated sulfuric acid typically proceeds via an E1 mechanism, which involves the formation of a carbocation intermediate. The formation of trans-2-butene suggests a hydride shift occurred to form a more stable carbocation before elimination.

Question 20

What is Zaitsev's rule?

Accepted Answer

The answer of What is Zaitsev's rule?...

Quiz 6: Alkyl Halides; Nucleophilic Substitution

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

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.

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

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

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

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.

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

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

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

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

Provide two circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

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

S_N1 reactions usually proceed with ________.

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.

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

When a S_N1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

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.

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?

What is Zaitsev's rule?

Quiz 6: Alkyl Halides; Nucleophilic Substitution

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

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.

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

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

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

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.

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

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

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

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

Provide two circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

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

SN1 reactions usually proceed with ________.

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.

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

When a SN1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

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.

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?

What is Zaitsev's rule?

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

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

S_N1 reactions usually proceed with ________.

When a S_N1 reaction of R-2-iodobutane takes place in hot methanol, the product ________.

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?