Give complete mechanism of following reactions: CH, 0-H HBr CH; --C-CH–CH, → (CH,), C–CE–CH; a. H;O b. CH, Br + (CH;)C- CH = CH; + (CH) ;С— сH (сH); + (CH3); C = C (CH,); CH2 =C-CH (CH;)? CH3

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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**Transcription for Educational Website**

---

**Topic: Reaction Mechanisms**

**I. Give complete mechanism of following reactions:**

**a.**

1. \( \text{CH}_3 \, \overset{\text{H}}{\underset{\text{O}}{-}} \, \text{C} \, \text{CH} \, \text{CH}_3 \xrightarrow{\text{HBr}} \text{(CH}_3\text{)}_3 \, \text{C} \, \overset{\text{Br}}{\underset{\text{CH}_3}{\equiv}} \)

   \( \text{H}_2\text{O} \)

   - Intermediate: \(\text{A}\)

   - By-products: \(\text{(CH}_3\text{)}_3 \text{C} \equiv \text{CH}_2 + (\text{CH}_3)_2 \text{C} = \text{CH(CH}_3)_2\)

   - By-products: \(\text{D}\), \(\text{E}\)

**b.**

- Reactants: A hydrocarbon chain undergoes a reaction with \(\text{H}_3\text{O}^+\), leading to a cyclic product.

**c.**

- Reactants: A substituted benzene ring reacts with a hydrocarbon chain, forming a new carbon-carbon bond with retention of the substituents.

---

### Detailed Diagram Explanation:

**Reaction a:**

- **Mechanism:**
  - The primary alcohol reacts with HBr, resulting in the formation of a tertiary alkyl bromide.
  - Water is expelled during the reaction.
  - The process progresses through intermediates denoted by symbols \(\text{A}\), \(\text{D}\), and \(\text{E}\).

**Reaction b:**

- **Diagram Description:**
  - The linear hydrocarbon chain reacts in an acidic aqueous medium. The reaction yields a cyclized product, suggesting intramolecular bonding facilitated by hydronium ion (\(\text{H}_3\text{O}^+\)) catalysis.

**Reaction c:**

- **Diagram Description:**
  - The image shows the interaction between a substituted benzene ring featuring a bulky group and an aliphatic hydrocarbon chain. The formation of a new covalent
Transcribed Image Text:**Transcription for Educational Website** --- **Topic: Reaction Mechanisms** **I. Give complete mechanism of following reactions:** **a.** 1. \( \text{CH}_3 \, \overset{\text{H}}{\underset{\text{O}}{-}} \, \text{C} \, \text{CH} \, \text{CH}_3 \xrightarrow{\text{HBr}} \text{(CH}_3\text{)}_3 \, \text{C} \, \overset{\text{Br}}{\underset{\text{CH}_3}{\equiv}} \) \( \text{H}_2\text{O} \) - Intermediate: \(\text{A}\) - By-products: \(\text{(CH}_3\text{)}_3 \text{C} \equiv \text{CH}_2 + (\text{CH}_3)_2 \text{C} = \text{CH(CH}_3)_2\) - By-products: \(\text{D}\), \(\text{E}\) **b.** - Reactants: A hydrocarbon chain undergoes a reaction with \(\text{H}_3\text{O}^+\), leading to a cyclic product. **c.** - Reactants: A substituted benzene ring reacts with a hydrocarbon chain, forming a new carbon-carbon bond with retention of the substituents. --- ### Detailed Diagram Explanation: **Reaction a:** - **Mechanism:** - The primary alcohol reacts with HBr, resulting in the formation of a tertiary alkyl bromide. - Water is expelled during the reaction. - The process progresses through intermediates denoted by symbols \(\text{A}\), \(\text{D}\), and \(\text{E}\). **Reaction b:** - **Diagram Description:** - The linear hydrocarbon chain reacts in an acidic aqueous medium. The reaction yields a cyclized product, suggesting intramolecular bonding facilitated by hydronium ion (\(\text{H}_3\text{O}^+\)) catalysis. **Reaction c:** - **Diagram Description:** - The image shows the interaction between a substituted benzene ring featuring a bulky group and an aliphatic hydrocarbon chain. The formation of a new covalent
### Reaction Scheme for Aldol Reaction

#### Part d:
This part of the reaction involves the formation of a carbonyl compound via an Aldol reaction. The process is described as follows:

1. **Starting Materials:**
   - A compound with a carbonyl group (\( \text{C=O} \)) and an attached hydrogen (\( \text{C-H} \)).
   - Reacts with sodium hydride (\( \text{NaCH} \)) and a benzyl compound (\( \text{C} \) - \( \text{BR} \)).

2. **Reaction Process:**
   - In the first step, sodium hydride (\( \text{NaCH} \)) is used.

3. **Reaction Outcome:**
   - The product is a benzyl-ketone with a carbonyl group attached to the benzene ring: \( \text{C} \) - \( \text{O} \)-\( \text{C=O} \).

#### Part e:
This part focuses on the stereochemistry and the formation of a racemic mixture.

1. **Starting Materials:**
   - An \( \text{R-isomer} \) of a benzyl compound with a leaving group (\( \text{BR} \)).
   - Acetone (\( \text{CH}_3-\overset{\uparrow}{C}=O-\overset{\uparrow}{H} \)).

2. **Reaction Outcome:**
   - The isomer reacts to form a racemic mixture of the product, which is a benzene derivative with a ketone (\( \text{O} = \overset{\uparrow}{C}-\overset{\uparrow}{CH}_3 \)) group.
   - Byproduct is \( \text{HBY} \).

### Explanation:
The reaction outlines the transformation of reactants using basic organic reaction techniques such as the Aldol reaction. The stereochemical notation indicates consideration of chiral centers, resulting in racemic mixtures.
Transcribed Image Text:### Reaction Scheme for Aldol Reaction #### Part d: This part of the reaction involves the formation of a carbonyl compound via an Aldol reaction. The process is described as follows: 1. **Starting Materials:** - A compound with a carbonyl group (\( \text{C=O} \)) and an attached hydrogen (\( \text{C-H} \)). - Reacts with sodium hydride (\( \text{NaCH} \)) and a benzyl compound (\( \text{C} \) - \( \text{BR} \)). 2. **Reaction Process:** - In the first step, sodium hydride (\( \text{NaCH} \)) is used. 3. **Reaction Outcome:** - The product is a benzyl-ketone with a carbonyl group attached to the benzene ring: \( \text{C} \) - \( \text{O} \)-\( \text{C=O} \). #### Part e: This part focuses on the stereochemistry and the formation of a racemic mixture. 1. **Starting Materials:** - An \( \text{R-isomer} \) of a benzyl compound with a leaving group (\( \text{BR} \)). - Acetone (\( \text{CH}_3-\overset{\uparrow}{C}=O-\overset{\uparrow}{H} \)). 2. **Reaction Outcome:** - The isomer reacts to form a racemic mixture of the product, which is a benzene derivative with a ketone (\( \text{O} = \overset{\uparrow}{C}-\overset{\uparrow}{CH}_3 \)) group. - Byproduct is \( \text{HBY} \). ### Explanation: The reaction outlines the transformation of reactants using basic organic reaction techniques such as the Aldol reaction. The stereochemical notation indicates consideration of chiral centers, resulting in racemic mixtures.
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