Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Reaction Mechanism: Nucleophilic Substitution**
**Objective:** Show the full curved arrow mechanism for the following reaction, clearly showing how the indicated product is formed.
**Reaction Components:**
- Starting Material: A cyclic compound with a bromine (Br) atom attached
- Reactant: Water (H₂O)
**Reaction Equation:**
Cyclic bromine compound + H₂O → Cyclic alcohol compound
**Description of Mechanism:**
1. **Initial Step:** The bromine (Br) atom leaves the cyclic compound, forming a carbocation. This step involves the breaking of the carbon-bromine bond, shown by a curved arrow moving from the bond to the Br atom, indicating electron movement.
2. **Nucleophilic Attack:** The water molecule acts as a nucleophile, attacking the positively charged carbon (carbocation) where the Br was originally attached. This is represented by a curved arrow from one of the lone pairs on the oxygen in water to the carbocation.
3. **Proton Transfer:** After the attachment of water, a proton (H⁺) is removed to neutralize the positive charge on the oxygen, resulting in the formation of an OH group. This is typically shown by an additional step where another water molecule or a base removes the extra proton, though this is implicit here.
**Final Product:**
- The result is an alcohol where the -OH group has replaced the bromine atom on the cyclic compound. The cyclic structure remains intact with a substituent change from Br to OH.
This mechanism outlines the transformation of an alkyl halide to an alcohol through a nucleophilic substitution reaction (SN1 mechanism), commonly encountered in organic chemistry education.
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