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 20 OH H₂O :OH H3C Previous Next> OH H CH3 H3C CH3 +

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**Nucleophilic Substitution and Elimination Reactions of Alkyl Halides**

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 termed S_N1 for substitution and E1 for elimination.

**S_N1 and E1 Reactions:**
- 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 step, the nucleophile adds to the carbocation in S_N1 reaction or elimination occurs to give an alkene in the E1 reaction.
- Because the carbocation is planar, the nucleophile can add to either face, resulting in a racemic mixture, though solvent effects can influence this.

**Conditions Favoring S_N1/E1 Pathways:**
- Use of a weak nucleophile and a polar protic solvent.
- Same reaction conditions apply for both S_N1 and E1 reactions, making it difficult to predict which pathway (substitution or elimination) will predominate, leading to a mixture of products.

**Comparison between E1 and E1cB Reactions:**
- E1cB reactions involve carbocation intermediates, base-induced abstraction of a proton in a slow, rate-limiting step that gives an anion whence the leaving group leaves from the adjacent carbon.
- Particularly suited to the elimination of substrates with poor leaving groups stabilized by a carbonyl group, favoring the E1cB pathway over E1 and E2 reactions.

**Mechanistic Details:**
- The diagram explains the electron movement in the E1cB reaction mechanism.
  
**Arrow-pushing Instructions:**
- Typically represented by curved arrows indicating the movement of electrons during the mechanism.

**Illustration Description:**
- The diagram depicts a step in the reaction mechanism showing an OH group attached to a molecule (which includes CH3, H, and a carbonyl group) leaving as OH- to form a charged intermediate and a water molecule.

**Detailed Explanation of Diagram:**
- The molecule initially loses an OH- group.
- This process is assisted by the presence of a carbonyl group, which helps stabilize the intermediate through resonance.
- The final product shows a resonance-stabilized intermediate and a water molecule resulting from the
Transcribed Image Text:**Nucleophilic Substitution and Elimination Reactions of Alkyl Halides** 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 termed S_N1 for substitution and E1 for elimination. **S_N1 and E1 Reactions:** - 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 step, the nucleophile adds to the carbocation in S_N1 reaction or elimination occurs to give an alkene in the E1 reaction. - Because the carbocation is planar, the nucleophile can add to either face, resulting in a racemic mixture, though solvent effects can influence this. **Conditions Favoring S_N1/E1 Pathways:** - Use of a weak nucleophile and a polar protic solvent. - Same reaction conditions apply for both S_N1 and E1 reactions, making it difficult to predict which pathway (substitution or elimination) will predominate, leading to a mixture of products. **Comparison between E1 and E1cB Reactions:** - E1cB reactions involve carbocation intermediates, base-induced abstraction of a proton in a slow, rate-limiting step that gives an anion whence the leaving group leaves from the adjacent carbon. - Particularly suited to the elimination of substrates with poor leaving groups stabilized by a carbonyl group, favoring the E1cB pathway over E1 and E2 reactions. **Mechanistic Details:** - The diagram explains the electron movement in the E1cB reaction mechanism. **Arrow-pushing Instructions:** - Typically represented by curved arrows indicating the movement of electrons during the mechanism. **Illustration Description:** - The diagram depicts a step in the reaction mechanism showing an OH group attached to a molecule (which includes CH3, H, and a carbonyl group) leaving as OH- to form a charged intermediate and a water molecule. **Detailed Explanation of Diagram:** - The molecule initially loses an OH- group. - This process is assisted by the presence of a carbonyl group, which helps stabilize the intermediate through resonance. - The final product shows a resonance-stabilized intermediate and a water molecule resulting from the
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