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...
Related questions
Question
Please help me with the last problem! As you can see I got 3 out of them right

Transcribed Image Text:### Organic Chemistry Reaction Mechanism
This diagram illustrates a series of organic chemistry reactions starting from a cycloalkene. The steps involved can be summarized as follows:
#### Reagents and Intermediates
- **Lindlar's Catalyst**
- **H₂/Pt (Platinum)**
- **KMnO₄ (Potassium permanganate), OH⁻ (Warm)**
- **H₃O⁺ (Hydronium ion)**
- **Cl₂ (Chlorine), 2 equivalents**
#### Reaction Steps
1. **Initial Cycloalkene**
- The starting material is a cycloalkene, specifically a cyclohexene with one double bond and two methyl groups attached at the 1 and 3 positions.
2. **Reaction Pathways**
- The initial cycloalkene can react via two distinct pathways, indicated by the branching arrows.
3. **Pathway 1: Lindlar's Catalyst**
- This pathway involves the selective hydrogenation of the cycloalkene using Lindlar's catalyst, which results in a partially hydrogenated product. The intermediate or product is not explicitly shown here, but typically it would be a cyclohexene with a reduced number of double bonds.
4. **Pathway 2: KMnO₄, OH⁻ (Warm) followed by H₃O⁺**
- This pathway involves a two-step reaction:
- Step 1: The cycloalkene reacts with potassium permanganate (KMnO₄) in a warm, basic medium (OH⁻). This step usually results in the cleavage of the double bond and the formation of a diol or an oxidized product.
- Step 2: The intermediate product from the first step is then treated with hydronium ions (H₃O⁺), leading to further oxidation or rearrangement. The specific product is a cyclohexane derivative with single hydrogen atoms added at the positions previously holding the double bond.
5. **Pathway 3: Chlorination using Cl₂**
- This pathway involves the reaction of the cycloalkene with 2 equivalents of chlorine (Cl₂). The cycloalkene is converted into a cycloalkane with two chlorine atoms added at each carbon that was part of the original double bond.
#### Final Products
- **Product 1: From Lindlar’s Catalyst and

2. **Complete Hydrogenation**
- Reagent: H₂
- Catalyst: Pt (Platinum)
- Expected Product: This reaction fully hydrogenates the alkyne to produce an alkane with double the number of hydrogen atoms.

3. **Oxidation**
- Reagent 1: KMnO₄, OH⁻ (warm)
- Reagent 2: H₃O⁺
- Expected Product: This reaction will cleave the triple bond and form carboxylic acids at the ends of the structure.

4. **Halogenation**
- Reagent: Cl₂ (2 equiv)
- Expected Product: This reaction adds chlorine atoms to both carbons of the triple bond, resulting in a tetrachlorinated compound.

#### Explanation of Diagrams:
**Lindlar's Catalyst:**
- The diagram shows a flowchart where the alkyne starting material at the bottom center produces a cis-alkene at the top left when H₂/Lindlar's catalyst is used.
**Complete Hydrogenation:**
- The same alkyne starting material produces an alkane at the top right when H₂/Pt is used.
**Oxidation:**
- The alkyne starting material leads to two carboxylic acid products following the steps of oxidation with KMnO₄, OH⁻ (warm) and then H₃O⁺.
**Halogenation:**
- The alkyne starting material results in a tetrachlorinated](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fbb055132-6643-4863-94d3-885987d27e32%2Fc722aa1b-0089-4a1d-93e4-e5579efba23b%2Fjjo0tv_processed.png&w=3840&q=75)
Transcribed Image Text:### Problem 14 of 14
#### Question:
A common alkyne starting material is shown below. Predict the major product for each reaction. Ignore any inorganic byproducts.
#### Alkyne Starting Material:
- A cyclic alkyne is provided. The structure consists of a cyclo-octene ring with a triple bond and a methyl group attached.
#### Reactions:
1. **Reduction with Lindlar's Catalyst**
- Reagent: H₂
- Catalyst: Lindlar's catalyst
- Expected Product: This reaction partially hydrogenates the alkyne to a cis-alkene.

2. **Complete Hydrogenation**
- Reagent: H₂
- Catalyst: Pt (Platinum)
- Expected Product: This reaction fully hydrogenates the alkyne to produce an alkane with double the number of hydrogen atoms.

3. **Oxidation**
- Reagent 1: KMnO₄, OH⁻ (warm)
- Reagent 2: H₃O⁺
- Expected Product: This reaction will cleave the triple bond and form carboxylic acids at the ends of the structure.

4. **Halogenation**
- Reagent: Cl₂ (2 equiv)
- Expected Product: This reaction adds chlorine atoms to both carbons of the triple bond, resulting in a tetrachlorinated compound.

#### Explanation of Diagrams:
**Lindlar's Catalyst:**
- The diagram shows a flowchart where the alkyne starting material at the bottom center produces a cis-alkene at the top left when H₂/Lindlar's catalyst is used.
**Complete Hydrogenation:**
- The same alkyne starting material produces an alkane at the top right when H₂/Pt is used.
**Oxidation:**
- The alkyne starting material leads to two carboxylic acid products following the steps of oxidation with KMnO₄, OH⁻ (warm) and then H₃O⁺.
**Halogenation:**
- The alkyne starting material results in a tetrachlorinated
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 1 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY