Which of the following reaciton sequences will produce the diol shown in the highest yield? (A) РСС 1) xs CH3M9B NaBH4 OH но H. CH2CI2 2) H20 CH3OH HO NABH4 TMSCI 1) xs CH3M9B OH OCH3 CH3OH EtN 2) H30* HO OH TMSCI 1) xs CH3MGB TBAF (C) HO HO Et3N 2) H20 OH 1) LIAIH4 1) xs CH3MgBr (D) OCH3 HO 2) H20 2) H30*
Which of the following reaciton sequences will produce the diol shown in the highest yield? (A) РСС 1) xs CH3M9B NaBH4 OH но H. CH2CI2 2) H20 CH3OH HO NABH4 TMSCI 1) xs CH3M9B OH OCH3 CH3OH EtN 2) H30* HO OH TMSCI 1) xs CH3MGB TBAF (C) HO HO Et3N 2) H20 OH 1) LIAIH4 1) xs CH3MgBr (D) OCH3 HO 2) H20 2) H30*
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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The answer is C, but I need help with the explanation. Why is c?
![**Question:**
Which of the following reaction sequences will produce the diol shown in the highest yield?
**Options:**
(A)
- Starting Material: \[\text{HO}\hspace{2mm}\text{(CH}_2)_2\text{CHO}\]
- Reagents:
1. PCC, \[\text{CH}_2\text{Cl}_2\]
2. Excess \[\text{CH}_3\text{MgBr}\], \[\text{H}_2\text{O}\]
3. \[\text{NaBH}_4\], \[\text{CH}_3\text{OH}\]
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(B)
- Starting Material: \[\text{HCO}\hspace{2mm}\text{(CH}_2)_2\text{OCH}_3\]
- Reagents:
1. \[\text{NaBH}_4\], \[\text{CH}_3\text{OH}\]
2. TMSCl, \[\text{Et}_3\text{N}\]
3. Excess \[\text{CH}_3\text{MgBr}\]
4. \[\text{H}_3\text{O}^+\]
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(C)
- Starting Material: \[\text{HO}\hspace{2mm}\text{(CH}_2)_2\text{CHO}\]
- Reagents:
1. TMSCl, \[\text{Et}_3\text{N}\]
2. Excess \[\text{CH}_3\text{MgBr}\]
3. TBAF
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(D)
- Starting Material: \[\text{HCO}\hspace{2mm}\text{(CH}_2)_2\text{OCH}_3\]
- Reagents:
1. \[\text{LiAlH}_4\](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F3890751a-c083-48b5-a28b-4eb600d685a2%2Fb99dd585-a971-45c1-a99c-61b7a1dd9459%2Fw5dyszl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Question:**
Which of the following reaction sequences will produce the diol shown in the highest yield?
**Options:**
(A)
- Starting Material: \[\text{HO}\hspace{2mm}\text{(CH}_2)_2\text{CHO}\]
- Reagents:
1. PCC, \[\text{CH}_2\text{Cl}_2\]
2. Excess \[\text{CH}_3\text{MgBr}\], \[\text{H}_2\text{O}\]
3. \[\text{NaBH}_4\], \[\text{CH}_3\text{OH}\]
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(B)
- Starting Material: \[\text{HCO}\hspace{2mm}\text{(CH}_2)_2\text{OCH}_3\]
- Reagents:
1. \[\text{NaBH}_4\], \[\text{CH}_3\text{OH}\]
2. TMSCl, \[\text{Et}_3\text{N}\]
3. Excess \[\text{CH}_3\text{MgBr}\]
4. \[\text{H}_3\text{O}^+\]
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(C)
- Starting Material: \[\text{HO}\hspace{2mm}\text{(CH}_2)_2\text{CHO}\]
- Reagents:
1. TMSCl, \[\text{Et}_3\text{N}\]
2. Excess \[\text{CH}_3\text{MgBr}\]
3. TBAF
- Product: \[\text{HO-CH}_2\text{CH}_2\text{CH}-\text{OH}\]
(D)
- Starting Material: \[\text{HCO}\hspace{2mm}\text{(CH}_2)_2\text{OCH}_3\]
- Reagents:
1. \[\text{LiAlH}_4\
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