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[Review Topics] [References] CH3 OMe H3C. CH3 MeOH CH3 CH3 CH3 H3C H3C H3C Br Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both SN1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the ElcB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air

[Review Topics] [References] CH3 OMe H3C. CH3 MeOH CH3 CH3 CH3 H3C H3C H3C Br Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both SN1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the ElcB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air

Physical Chemistry
Physical Chemistry
2nd Edition
ISBN:9781133958437
Author:Ball, David W. (david Warren), BAER, Tomas
Publisher:Ball, David W. (david Warren), BAER, Tomas
Chapter20: Kinetics
Section: Chapter Questions
Problem 20.87E: Pyrolysis involves heating compounds to break them into smaller molecules, and typically involves...
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myCoyote OWlv2 Homework Registration: CHEM 2... C OWLV2 | Online teaching and learning res.. * Start [Review Topics] [References) CH3 OMe H3C. CH3 MeOH CH3 CH3 CH3 H3C H3C H3C Br Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both SN1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the E1cB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air 80 DII DD F3 F4 F5 F6 F7 F8 F9 F10 F11 F12 $ & * 4 6. 8. 9 { } Y U G J K L + || ...- ト
Transcribed Image Text:myCoyote OWlv2 Homework Registration: CHEM 2... C OWLV2 | Online teaching and learning res.. * Start [Review Topics] [References) CH3 OMe H3C. CH3 MeOH CH3 CH3 CH3 H3C H3C H3C Br Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both SN1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the E1cB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air 80 DII DD F3 F4 F5 F6 F7 F8 F9 F10 F11 F12 $ & * 4 6. 8. 9 { } Y U G J K L + || ...- ト
[Review Topics] [References] elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both Sy1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the E1CB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 MEOH CH3 H3C H3C H H H Submit Answer Retry Entire Group 8 more group attempts remaining Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air 80 DII DD F4 F3 F5 F6 F7 F8 F9 F10 F11 F12 & 4. 6 7 8 9 del { R Y [ F H. J K V M. 1V
Transcribed Image Text:[Review Topics] [References] elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak nucleophile and a polar protic solvent. The same reaction conditions apply for both Sy1 and E1, therefore these reactions will compete. It is usually difficult to predict which pathway, substitution or elimination, will predominate and so a mixture of products is frequently observed. In contrast to the E1 reaction which involves a carbocation intermediate, the E1CB reaction takes place through a carbanion intermediate. Base-induced abstraction of a proton in a slow, rate-limiting step gives an anion which then expels the leaving group from the adjacent carbon. The reaction is particularly suited to the elimination of substrates which contain poor leaving groups two carbons removed from a carbonyl group. The poor leaving group disfavors the alternative E1 and E2 reactions, and the carbonyl group helps to stabilize the anion via resonance. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 MEOH CH3 H3C H3C H H H Submit Answer Retry Entire Group 8 more group attempts remaining Previous Next Email Instructor Save and Exit Cengage Learning | Cengage Technical Support MacBook Air 80 DII DD F4 F3 F5 F6 F7 F8 F9 F10 F11 F12 & 4. 6 7 8 9 del { R Y [ F H. J K V M. 1V
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ISBN:
9781133958437
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Publisher:
Wadsworth Cengage Learning,
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