Interpretation:
The complete and detailed mechanisms for the
Concept introduction:
Answer to Problem 9.1P
The mechanism for SN2 reaction:
The mechanism for SN1 reaction:
The mechanism for E2 reaction:
The mechanism for E1 reaction:
Explanation of Solution
In the case of an SN2 mechanism, the nucleophile attacks the reactant, and at the same time, the leaving group departs. So the SN2 mechanism is a one-step reaction. As the nucleophile ammonia is neutral, an unstable charged species is formed.
The base, another molecule of ammonia, extracts a proton from the charged species to form the stable, final product.
Therefore, the complete mechanism can be shown as below:
An SN1 mechanism is a two-step mechanism. In the first step, the leaving group departs along with the electron pair from its bond with the carbon atom. This generates a carbocation.
In the second step, the nucleophile ammonia uses the lone pair on nitrogen to form a bond with the carbocation to form a charged species.
In the final step, another molecule of ammonia acts as a base and extracts a proton from the
Therefore, the complete mechanism can be shown as below:
In the case of an E2 mechanism, ammonia acts as a base and abstracts a proton from a carbon atom adjacent to the one attached to the leaving group. The
Therefore, the complete mechanism can be shown as below:
In the case of an E1 mechanism, the leaving group iodine departs with its bond pair, as an iodide anion. This forms the carbocation.
In the second step, ammonia acts as a base and extracts a proton from a carbon adjacent to the positively charged carbon. The
Therefore, the complete mechanism for the E1 reaction can be shown as below:
In a nucleophilic substitution reaction, the attacking species acts as a nucleophile while in an elimination reaction, it acts as a base.
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Chapter 9 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Draw the mechanism for this reaction. HO H,SO4.arrow_forwardis this an E1 or E2 mechanism for this reaction? What is the major product and step by step mechanism?arrow_forwardFor each set of reactions, circle the mechanism (SN2 vs SN1), draw the main organic substitution/elimination product (for each reaction draw the product, though in some cases it may be equivalent) and indicate which reaction occurs at the faster rate.arrow_forward
- The following reaction has three different products. Draw the mechanisms to find them and mention which one out of the three is the major product.arrow_forwardDraw the reaction mechanism of the following reaction in acidic conditions. List allpossible compounds in the reaction mixture right after you stop the reactionarrow_forwardA student proposes the following reaction mechanism for the reaction in Model 6. Which step inthis mechanism is least favorable? Explain your reasoning.arrow_forward
- Complete the reactions below, draw the mechanism for each reaction, and determine majorand minor products where applicable.arrow_forwardDraw the mechanisms and products for the following reactionsarrow_forwardDraw the complete mechanism for the following reaction. Predict the product(s) as well. Br₂arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning