Predict the product of the following transformation. A ora t-Bu Me B t-Bu 1. 2. t-BUCI, AICI3 Me 3. RaNi, H₂, EtOH SH HS p-TSOH (cat.) PhH, reflux Me D O t-Bu Axir C S S t-Bu Me Me O E t-Bu Me

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...
icon
Related questions
Question
## Question 3

**Predict the product of the following transformation.**

### Reaction Steps:
1. Reagents: HS(CH2)2SH, p-TsOH (catalytic), PhH, reflux
2. Reagents: t-BuCl, AlCl3
3. Reagents: RaNi, H2, EtOH

### Options:
- **A** 
- **B** 
- **C** 
- **D** 
- **E** 

### Description of Structures:
- **A**: A compound with a tert-butyl group attached to a phenyl ring and a methyl group on a cyclohexane.
- **B**: Similar to A, but with different orientations of substituents.
- **C**: Contains a sulfur bridge between two phenyl rings and a tert-butyl group.
- **D**: Features a carbonyl group adjacent to a tert-butyl group on a phenyl ring.
- **E**: Similar to D with a cyclohexane structure.

**Correct Answer:** 1. A
Transcribed Image Text:## Question 3 **Predict the product of the following transformation.** ### Reaction Steps: 1. Reagents: HS(CH2)2SH, p-TsOH (catalytic), PhH, reflux 2. Reagents: t-BuCl, AlCl3 3. Reagents: RaNi, H2, EtOH ### Options: - **A** - **B** - **C** - **D** - **E** ### Description of Structures: - **A**: A compound with a tert-butyl group attached to a phenyl ring and a methyl group on a cyclohexane. - **B**: Similar to A, but with different orientations of substituents. - **C**: Contains a sulfur bridge between two phenyl rings and a tert-butyl group. - **D**: Features a carbonyl group adjacent to a tert-butyl group on a phenyl ring. - **E**: Similar to D with a cyclohexane structure. **Correct Answer:** 1. A
**Question 3**

**Predict the product of the following transformation.**

The starting material is an aromatic ketone with additional phenyl and methyl groups. The transformation involves three steps:

1. Reagents: HS(CH2)3SH, p-TsOH (cat.), PhH, reflux
2. Reagents: t-BuCl, AlCl3
3. Reagents: RaNi, H2, EtOH

The objective is to determine which compound (A, B, C, D, or E) is the final product of the reaction sequence.

**Options:**

- **A**: Contains a phenyl group attached to a tert-butyl group and a methyl group.
- **B**: Similar to A but with a different aromatic substitution pattern.
- **C**: Features a thioether linkage (S-S) and a tert-butyl group.
- **D**: Contains a ketone functional group, a tert-butyl group, and a methyl group.
- **E**: Similar to D but with a cycloalkyl group instead of a direct aromatic substitution.

**Choices:**
1. A
2. B
3. C
4. D
5. E

The student needs to choose the correct option that represents the final product after applying the given reagents on the starting compound.
Transcribed Image Text:**Question 3** **Predict the product of the following transformation.** The starting material is an aromatic ketone with additional phenyl and methyl groups. The transformation involves three steps: 1. Reagents: HS(CH2)3SH, p-TsOH (cat.), PhH, reflux 2. Reagents: t-BuCl, AlCl3 3. Reagents: RaNi, H2, EtOH The objective is to determine which compound (A, B, C, D, or E) is the final product of the reaction sequence. **Options:** - **A**: Contains a phenyl group attached to a tert-butyl group and a methyl group. - **B**: Similar to A but with a different aromatic substitution pattern. - **C**: Features a thioether linkage (S-S) and a tert-butyl group. - **D**: Contains a ketone functional group, a tert-butyl group, and a methyl group. - **E**: Similar to D but with a cycloalkyl group instead of a direct aromatic substitution. **Choices:** 1. A 2. B 3. C 4. D 5. E The student needs to choose the correct option that represents the final product after applying the given reagents on the starting compound.
Expert Solution
Step 1

The conversion involves 

1) protection of keto functional group

2) Friedel-craft alkylation

3) deprotection and reduction with RaNi/H2

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Organic Mustards
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.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY