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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Question
Use curved arrows to show the flow of electrons on the reactant side of each of the following reactions:
![### Transcription of Chemical Reactions
#### Reaction (a):
1. **Reactants:**
- A compound with a phenyl group (benzene ring) attached to a carbonyl group (C=O) and adjacent to chlorine (C-Cl bond) with two hydrogen atoms.
- Hydroxide ion (OH⁻).
2. **Reaction Process:**
- The hydroxide ion attacks the carbon atom in the haloalkane, displacing the chloride ion.
3. **Products:**
- A phenyl ketone with a negative charge on the oxygen and an extra lone pair (resonance structure).
- Water molecule (H₂O) produced as a byproduct.
#### Reaction (b):
1. **Reactants:**
- A secondary alcohol group with isopropyl groups on both sides (2-propanol).
- Hydrochloric acid (HCl).
2. **Reaction Process:**
- The hydrogen ion (H⁺) from HCl protonates the oxygen atom of the alcohol, turning it into a good leaving group.
- The chloride ion (Cl⁻) is displaced.
3. **Products:**
- A carbocation formed by the loss of the leaving hydrogen.
- Chloride ion (Cl⁻) remains.
### Diagram Explanation
Both diagrams illustrate nucleophilic substitution reactions where a nucleophile attacks an electrophilic center, leading to the substitution of a leaving group. Reaction (a) features a typical haloalkane and hydroxide ion interaction, while reaction (b) shows an acid-catalyzed reaction of an alcohol with hydrochloric acid.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4b6078a5-5329-4ddc-8cf0-0c10f5757356%2F86b7b175-ebfb-4840-b38a-f0651ced5b29%2Fjx7dl3i_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Transcription of Chemical Reactions
#### Reaction (a):
1. **Reactants:**
- A compound with a phenyl group (benzene ring) attached to a carbonyl group (C=O) and adjacent to chlorine (C-Cl bond) with two hydrogen atoms.
- Hydroxide ion (OH⁻).
2. **Reaction Process:**
- The hydroxide ion attacks the carbon atom in the haloalkane, displacing the chloride ion.
3. **Products:**
- A phenyl ketone with a negative charge on the oxygen and an extra lone pair (resonance structure).
- Water molecule (H₂O) produced as a byproduct.
#### Reaction (b):
1. **Reactants:**
- A secondary alcohol group with isopropyl groups on both sides (2-propanol).
- Hydrochloric acid (HCl).
2. **Reaction Process:**
- The hydrogen ion (H⁺) from HCl protonates the oxygen atom of the alcohol, turning it into a good leaving group.
- The chloride ion (Cl⁻) is displaced.
3. **Products:**
- A carbocation formed by the loss of the leaving hydrogen.
- Chloride ion (Cl⁻) remains.
### Diagram Explanation
Both diagrams illustrate nucleophilic substitution reactions where a nucleophile attacks an electrophilic center, leading to the substitution of a leaving group. Reaction (a) features a typical haloalkane and hydroxide ion interaction, while reaction (b) shows an acid-catalyzed reaction of an alcohol with hydrochloric acid.
![### Chemical Reaction Scheme (c)
This diagram illustrates a chemical reaction involving:
1. **Reactants:**
- A brominated alkane (CH₃CH₂CHBrCH₃), where bromine (Br) is attached to the third carbon in the carbon chain.
- A hydroxide ion (OH⁻).
2. **Conditions:**
- The reaction requires heat for the transformation to occur.
3. **Products:**
- An alkene (CH₃CH₂CH=CH₂), which is a four-carbon chain with a double bond between the second and third carbon atoms.
- A bromide ion (Br⁻), which is released from the brominated alkane.
- Water (H₂O), formed from the hydroxide ion and the hydrogen atom removed from the original alkane.
### Explanation
- **Mechanism:**
- This reaction is an example of an elimination reaction, specifically an E2 mechanism, where the base (OH⁻) abstracts a hydrogen atom adjacent to the carbon with the leaving group (Br), resulting in the formation of a double bond and the expulsion of the bromide ion.
- **Outcome:**
- The transformation converts a saturated alkane into an unsaturated alkene through the loss of a molecule of HBr, with heat facilitating the reaction.
This reaction is important in organic chemistry for the synthesis of alkenes from haloalkanes.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4b6078a5-5329-4ddc-8cf0-0c10f5757356%2F86b7b175-ebfb-4840-b38a-f0651ced5b29%2Fzucyuq_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Chemical Reaction Scheme (c)
This diagram illustrates a chemical reaction involving:
1. **Reactants:**
- A brominated alkane (CH₃CH₂CHBrCH₃), where bromine (Br) is attached to the third carbon in the carbon chain.
- A hydroxide ion (OH⁻).
2. **Conditions:**
- The reaction requires heat for the transformation to occur.
3. **Products:**
- An alkene (CH₃CH₂CH=CH₂), which is a four-carbon chain with a double bond between the second and third carbon atoms.
- A bromide ion (Br⁻), which is released from the brominated alkane.
- Water (H₂O), formed from the hydroxide ion and the hydrogen atom removed from the original alkane.
### Explanation
- **Mechanism:**
- This reaction is an example of an elimination reaction, specifically an E2 mechanism, where the base (OH⁻) abstracts a hydrogen atom adjacent to the carbon with the leaving group (Br), resulting in the formation of a double bond and the expulsion of the bromide ion.
- **Outcome:**
- The transformation converts a saturated alkane into an unsaturated alkene through the loss of a molecule of HBr, with heat facilitating the reaction.
This reaction is important in organic chemistry for the synthesis of alkenes from haloalkanes.
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