a) Styrene (PhCH=CH2)
Interpretation:
How to prepare styrene from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield
To state:
How to prepare styrene from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Styrene can be prepared by treating 2-phenylethanol with POCl3 in pyridine.
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 1](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap1.jpg)
Styrene can be prepared by treating 2-phenylethanol with POCl3 in pyridine.
b) Phenylacetaldehyde (PhCH2CHO)
Interpretation:
How to prepare phenylacetaldehyde from 2-phenylethanol is to be stated.
Concept introduction:
Dess-Martin periodinate in dichloromethane oxidizes 10alcohols to
To state:
How to prepare phenylacetaldehyde from 2-phenylethanol
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Phenylacetaldehyde can be prepared by oxidizing 2-phenylethanol with Dess-Martin periodinate in dichloromethane.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 2](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap2.jpg)
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to phenylacetaldehyde when treated with Dess-Martin periodinate in dichloromethane.
Phenylacetaldehyde can be prepared by oxidizing 2-phenylethanol with Dess-Martin periodinate in dichloromethane.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 3](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap2.jpg)
c) Phenylacetic acid (PhCH2COOH)
Interpretation:
How to prepare phenylacetic acid from 2-phenylethanol is to be stated.
Concept introduction:
CrO3 in acidic solutions oxidize 10 alcohols directly into acids and 20 alcohols to ketones. It does not oxidize 30 alcohols.
To state:
How to prepare phenylacetic acid from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Phenylacetic acid can be prepared by oxidizing 2-phenylethanol with CrO3 in acidic solutions.
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to phenylacetic acid when treated with CrO3 in acidic solutions.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 4](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap3.jpg)
Phenylacetic acid can be prepared by oxidizing 2-phenylethanol with CrO3 in acidic solutions.
d) Benzoic acid
Interpretation:
How to prepare benzoic acid from 2-phenylethanol is to be stated.
Concept introduction:
KMnO4 in acidic solutions oxidize
To state:
How to prepare benzoic acid from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Benzoic acid can be prepared by oxidizing 2-phenylethanol with KMnO4 in acidic solutions.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 5](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap4.jpg)
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to benzoic acid when treated with KMnO4 in acidic solutions.
Benzoic acid can be prepared by oxidizing 2-phenylethanol with KMnO4 in acidic solutions.
e) Ethylbenzene
Interpretation:
How to prepare ethylbenzene from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene upon reduction gives the
To state:
How to prepare ethylbenzene from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Ethylbenzene can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 6](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap5.jpg)
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When treated with H2/Pd, the double bond in the side chain gets reduced to yield ethyl benzene.
Ethylbenzene can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 7](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap5.jpg)
f) benzaldehyde
Interpretation:
How to prepare benzaldehyde from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene upon ozonolyzis followed by reduction will yield the aldehyde required.
To state:
How to prepare benzaldehyde from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
Benzaldehyde can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 8](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap6.jpg)
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When styrene is subjected to ozonolysis followed by reduction, the double bond in side chain gets cleaved resulting in the formation of benzaldehyde.
Benzaldehyde can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 9](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap6.jpg)
g) 1-phenylethanol
Interpretation:
How to prepare 1-phenylethanol from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene adds a molecule of water following oxymercuration-demercuration process. The addition will take place following Markovnikov regiochemistry.
To state:
How to prepare 1-phenylethanol from 2-phenylethanol.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
1- Phenylethanol can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 10](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap7.jpg)
Explanation of Solution
2-Phenylethanol, when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When styrene is subjected oxymercuration-demercuration processes, a molecule of water is added, following Markovnikov regiochemistry, to the double bond. The –OH adds on to the more alkyl substituted carbon and H to the less alkyl substituted carbon in double bond to yield 1-phenylethanol.
1-Phenylethanol can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 11](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap7.jpg)
h) 1-Bromo-2-phenylethane
Interpretation:
How to prepare 1-bromo-2-phenylethane from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols yield the corresponding alkyl bromides when treated with PBr3.
To state:
How to prepare 1-bromo-2-phenylethane from 2-phenylethanol is to be stated.
![Check Mark](/static/check-mark.png)
Answer to Problem 47AP
1-Bromo-2-phenylethane can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 12](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap8.jpg)
Explanation of Solution
When 2-phenylethanol is treated with PBr3, a bimolecular nucleophilic substitution of –OH by Br takes place to yield 1-bromo-2-phenylethane.
1-Bromo-2-phenylethane can be prepared from 2-phenylethanol by following the steps shown below.
![ORGANIC CHEMISTRY-EBOOK>I<, Chapter 17.SE, Problem 47AP , additional homework tip 13](https://content.bartleby.com/tbms-images/9781305080485/Chapter-17/images/80485-17-47ap8.jpg)
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Chapter 17 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
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- Predict which member of each pair is more acidic, and explain the reasons for your predictions.(a) cyclopentanol or 3-chlorophenol (b) cyclohexanol or cyclohexanethiol(c) cyclohexanol or cyclohexanecarboxylic acid (d) butan-1-ol or 2,2-dichlorobutan-1-olarrow_forward16-57 Starting with either benzene or toluene, how would you synthesize the following substances? Assume that ortho and para isomers can be separated. (a) 2-Bromo-4-nitrotoluene (c) 2,4,6-Tribromoaniline (b) 1,3,5-Trinitrobenzene (d) m-Fluorobenzoic acidarrow_forward3.) Starting from phenol, the synthesis of 2,4-dichlorophenoxyacetic acid involves four steps outlined by the roadmap below. Please provide the missing reagents and products where necessary. OH 1. NaOH HCl(aq) 2 Cl₂ FeCla OH 2,4-dichlorophenoxyacetic acid Iarrow_forward
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