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Alcohols, Ethers, and Phenols

Mark Ian Go Pascua

University of the Philippines Diliman, Quezon City, Philippines

Performed Sept 20 2019; Submitted 25 September 2019

ANSWERS TO QUESTIONS

1. Give the balanced chemical equations for all the reactions

 Isopropyl(Lucas Reagent)

 Tert-butanol(Lucas Reagent)

 Benzyl Alcohol(Lucas Reagent)

 Ethyl Alcohol(Oxidation)

 Isopropyl Alcohol(Oxidation)

Mark Ian Go Pascua. Mobile: 09262990344

E-mail Add:leoriser@gmail.com
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 Benzyl Alcohol(Oxidation)

 Diethyl Ether(Oxidation)

 Phenol(Br2 in H2O)

+ 3HBr
 Phenol(KMnO4)

 Phenol(FeCl3)

 P-Nitrophenol(FeCl3)

 Β-Naphtol(FeCl3)
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2. Why is the Lucas Test only applicable to alcohols containing 5 or less carbons?
 Because alcohols containing more than 5 carbons may produce a false positive when exposed to the Lucas
reagent.[1]
3. Why do tertiary alcohols and ethers not oxidize upon reaction with potassium permanganate?
 They don’t oxidize upon reaction with potassium permanganate because the tertiary alcohol’s connected
carbon has 3 C-C bonds which are much harder to break than a secondary or primary alcohol’s C-H
bond.[2]

4. Explain the relationship between the structures of the phenolic compounds with their expected pH values.
Test Sample Expected Explanation
pH
6 The OH group can easily donate a proton, a characteristic of a
Bronsted-lowry acid, which makes the compound slightly acidic.[3]

Phenol
3 There is a presence of an OH group which slightly contributes to the
acidic nature of the sample, but the nitrogen with the positive
charge will be very easily donate a proton, moreso than an OH
group alone. This makes the compound very acidic

p-Nitrophenol
1.3 in There is a far greater number of proton donating groups in picric
saturated acid than the previous samples and therefore the acidity of picric
solution. acid is far greater than the previous samples.

Picric Acid
5 Β-Naphthol only has 1 proton donating group which is an OH group.
This leads to it only being slightly acidic.

β -Naphthol

REFERENCES
[1]Nichols, L. Organic Chemistry Laboratory Techniques 2nd Edition. Butte Community College, 2017.
[2]McMurry, John E. 2007. Organic Chemistry 7/E. Brooks-Cole, New York
[3]Solomons, T. W. Graham, and Craig B. Fryhle. Organic Chemistry. John Wiley, Hoboken, NJ ,2008.
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