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.
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.
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
Answer to Problem 47AP
Phenylacetaldehyde can be prepared by oxidizing 2-phenylethanol with Dess-Martin periodinate in dichloromethane.
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.
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.
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.
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.
Answer to Problem 47AP
Benzoic acid can be prepared by oxidizing 2-phenylethanol with KMnO4 in acidic solutions.
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.
Answer to Problem 47AP
Ethylbenzene can be prepared from 2-phenylethanol by following the steps shown below.
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.
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.
Answer to Problem 47AP
Benzaldehyde can be prepared from 2-phenylethanol by following the steps shown below.
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.
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.
Answer to Problem 47AP
1- Phenylethanol can be prepared from 2-phenylethanol by following the steps shown below.
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.
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.
Answer to Problem 47AP
1-Bromo-2-phenylethane can be prepared from 2-phenylethanol by following the steps shown below.
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.
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Chapter 17 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
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