
Concept explainers
(a)
Interpretation:
It is to be determined whether the solvent would interfere with producing the intended target in the proposed synthetic step. For those that would, another solvent that can be used is to be suggested with an explanation.
Concept introduction:
Solvent plays an important role in the proposed synthetic step by not interfering with the reactant molecule or intermediates. For E2 elimination reactions, a strong base is used in the presence of a

Answer to Problem 13.33P
The solvent for the proposed synthetic step is appropriate. The proposed synthetic step is an example of an E2 reaction, which favors the Zaitsev product (most substituted alkene). If the solvent ethanol is deprotonated, the result is still an ethoxide ion which is the same base that is already shown.
Explanation of Solution
The given proposed synthetic step is:
The reactant molecule has a good leaving group,
The requirement of the solvent for E2 reactions is aprotic, as aprotic solvents do not solvate the anions (negatively charged ions) as strongly as they solvate cations (positively charged ions).
(b)
Interpretation:
It is to be determined whether the solvent would interfere with producing the intended target in the proposed synthetic step. For those that would, another solvent that can be used is to be suggested with an explanation.
Concept introduction:
Solvent plays an important role in the proposed synthetic step by not interfering with the reactant molecule or intermediates. For E2 elimination reactions, a strong base is used in the presence of a polar aprotic solvent to yield the most substituted alkene is the major product. The requirement of the solvent for E2 reactions is aprotic, as aprotic solvents do not solvate the anions (negatively charged ions) as strongly as they solvate cations (positively charged ions). If the base used in the reaction and the base produced by the deprotonation of solvent molecules is the same, then the reaction proceeds in the forward direction and the proposed synthetic step is valid and acceptable. If the base used in the reaction is different from the base produced by the deprotonation of solvent molecules, then they would compete and the proposed synthetic route then would not be the valid route.

Answer to Problem 13.33P
The solvent ethanol for the proposed synthetic step is not appropriate. The proposed synthetic step is an example of an E2 reaction, which favors the Zaitsev product (most substituted alkene). The alkoxide ion shown
Explanation of Solution
The given proposed synthetic step is:
The reactant molecule has a good leaving group,
The requirement of the solvent for E2 reactions is aprotic, as aprotic solvents do not solvate the anions (negatively charged ions) as strongly as they solvate cations (positively charged ions).
(c)
Interpretation:
It is to be determined whether the solvent would interfere with producing the intended target in the proposed synthetic step. For those that would, another solvent that can be used is to be suggested with an explanation.
Concept introduction:
Solvent plays an important role in the proposed synthetic step by not interfering with the reactant molecule or intermediates.
For a substitution reaction which follows

Answer to Problem 13.33P
The solvent ethanol for the proposed synthetic step is not appropriate. The proposed synthetic step is an example of a
Explanation of Solution
The given proposed synthetic step is:
The reactant molecule has a moderate leaving group,
A
Thus, the solvent ethanol will interfere in the proposed synthetic step. Instead of ethanol cyclohexanol should be used, which will generate the same anion that is cyclohexanolate ion or any other aprotic solvent such as DMSO could be used.
The requirement of the solvent for
(d)
Interpretation:
It is to be determined whether the solvent would interfere with producing the intended target in the proposed synthetic step. For those that would, another solvent that can be used is to be suggested with an explanation.
Concept introduction:
Solvent plays an important role in the proposed synthetic step by not interfering with the reactant molecule or intermediates.
For a substitution reaction which follows

Answer to Problem 13.33P
The solvent for the proposed synthetic step is appropriate. The proposed synthetic step is an example of an E2 reaction, which favors the Zaitsev product (most substituted alkene). If the solvent ethanol is deprotonated, the result is still an ethoxide ion which is the same base that is already shown.
Explanation of Solution
The given proposed synthetic step is:
The reactant molecule has a good leaving group,
The requirement of the solvent for
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Chapter 13 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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- Can I please get help with this? And can I please the lowest possible significant number?arrow_forwardWhat is the molar mass of a gas that takes three times longer to effuse than helium?arrow_forwardFirst image: I have to show the mecanism (with arows and structures) of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary Second image: I have to show the mecanism (with arrows and structures) for the reaction on the left, where the alcohol A is added fast in one portion its not an examarrow_forward
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- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
