Alcohols and Phenols

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Questions and Answers

What is the correct IUPAC name for an alcohol with a hydroxyl group (-OH) attached to the second carbon of a five-carbon chain and two methyl groups attached to the fourth carbon?

  • 4-Methyl-2-hexanol
  • 2,2-Dimethyl-4-pentanol
  • 2-Methyl-4-pentanol
  • 4,4-Dimethyl-2-pentanol (correct)

During the production of ethanol from glucose ($C_6H_{12}O_6$) via fermentation, what other major product is generated?

  • Carbon Dioxide ($CO_2$) (correct)
  • Carbon Monoxide (CO)
  • Hydrogen ($H_2$)
  • Methane ($CH_4$)

Which of the following statements correctly describes the classification of alcohols?

  • In a primary alcohol, the carbon atom bearing the -OH group is bonded to one other carbon atom. (correct)
  • A tertiary alcohol has the -OH group bonded to a carbon that is attached to one other carbon.
  • A secondary alcohol has the -OH group bonded to a carbon that is attached to three other carbons.
  • An aromatic alcohol contains a hydroxyl group directly bonded to a benzene ring.

Which of the following alcohols would be expected to react fastest in the Lucas test?

<p>tert-butyl alcohol (C)</p> Signup and view all the answers

A researcher is trying to identify an unknown alcohol. Upon performing the chromic acid test, the solution turns from orange to blue-green. What type of alcohol is most likely present?

<p>A secondary alcohol (B)</p> Signup and view all the answers

What is the primary utility of the Ferric Chloride test, as it pertains to the identification of alcohols and phenols?

<p>To detect the presence of a phenol (D)</p> Signup and view all the answers

What is the major reason that alcohols with more than 5 carbon atoms exhibit limited miscibility in water?

<p>The non-polar alkyl chain increases, diminishing the influence of the polar hydroxyl group. (A)</p> Signup and view all the answers

Which of the following properties correctly ranks the acidity of different types of alcohols?

<p>1° alcohols &gt; 2° alcohols &gt; 3° alcohols (B)</p> Signup and view all the answers

In the catalytic hydrogenation of CO to produce methanol ($CH_3OH$), what are the typical reaction conditions?

<p>High temperature (300-400 °C) and high pressure (200-300 atm) with a ZnO-$Cr_2O_3$ catalyst. (B)</p> Signup and view all the answers

A chemist performs the iodoform test on an unknown compound and observes the formation of a yellow-brown precipitate. Which of the following functional groups is most likely present in the unknown compound?

<p>A methyl ketone (C)</p> Signup and view all the answers

Which of the following reagents is used in the Lucas test to differentiate between primary, secondary, and tertiary alcohols?

<p>Hydrochloric acid and zinc chloride (B)</p> Signup and view all the answers

Considering the IUPAC nomenclature rules, how would you correctly name a straight-chain alcohol containing four carbon atoms and a hydroxyl group?

<p>Butanol (A)</p> Signup and view all the answers

In the context of alcohol production, what is meant by 'destructive distillation of wood'?

<p>Heating wood in the absence of air to produce methanol. (A)</p> Signup and view all the answers

What type of alcohol is benzyl alcohol, given its structure?

<p>Aromatic alcohol (D)</p> Signup and view all the answers

What is the key characteristic of the reaction in a positive chromic acid test for alcohols?

<p>Development of a blue-green color. (A)</p> Signup and view all the answers

Why do tertiary alcohols not react in the chromic acid test?

<p>They lack a hydrogen atom on the carbon bonded to the -OH group. (B)</p> Signup and view all the answers

If 1-butanol, 2-butanol, and tert-butyl alcohol are subjected to the Lucas test, what would be the expected order of reactivity (from fastest to slowest)?

<p>tert-butyl alcohol &gt; 2-butanol &gt; 1-butanol (C)</p> Signup and view all the answers

If a compound gives a violet solution in the Ferric Chloride test, which of the following functional groups is most likely present?

<p>Phenol (A)</p> Signup and view all the answers

What is the purpose of using acid-catalyzed hydration of ethene?

<p>To produce ethanol (A)</p> Signup and view all the answers

Which of the following statements correctly describes the miscibility of alcohols in water?

<p>3-carbon alcohols are miscible, while &gt;5-carbon alcohols are borderline miscible to immiscible. (B)</p> Signup and view all the answers

Flashcards

What is a Hydroxyl?

A functional group in organic chemistry with the structure –OH, consisting of an oxygen atom bonded to a hydrogen atom.

IUPAC naming of Alcohols

Select the longest carbon chain containing -OH group and change the suffix of the parent alkane from '-ane' to '-ol'.

What is Methanol (CH3OH)

The simplest alcohol, produced by destructive distillation of wood or catalytic hydrogenation of CO.

What is Ethanol?

The most produced alcohol, made via fermentation or acid-catalyzed hydration of ethene.

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What is a Primary (1°) alcohol?

Carbon bonded to one other carbon atom.

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What is a Secondary (2°) alcohol?

Carbon bonded to Carbon bonded to two other carbon atoms.

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What is a Tertiary (3°) alcohol?

Carbon bonded to three other carbon atoms.

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What is Aromatic alcohol?

When -OH is bonded aromatic hydrocarbon. Note: Phenol is not an aromatic alcohol

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Miscibility in Water

3-carbon alcohols are fully miscible.

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Acidity and Basicity of Alcohols

Degree of acidity: 1° alcohols > 2° alcohols > 3° alcohols

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Lucus Test

Distinguishes between 3°, 2° and 1° alcohols based on reaction time.

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Chromic acid test for alcohols

Positive reaction forms a blue-green color.

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What is lodoform test?

Positive reaction forms yellow-brown precipitate.

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What is Ferric chloride test?

Positive reaction forms a violet solution.

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Study Notes

  • Alcohols and phenols are organic compounds that contain hydroxyl (-OH) groups.

IUPAC Nomenclature of Alcohols

  • When naming alcohols, select the longest chain containing the hydroxyl group.
  • Change the suffix of the parent alkane from "-ane" to "-ol".
  • Number the parent chain to give the hydroxyl group the lowest possible number.
  • Other substituents are named and numbered according to their positions.
  • Common names of simple alcohols are still used and approved by IUPAC.
  • Examples of alcohols include Isopropyl alcohol (Isopropanol), Ethanol (Ethyl Alcohol)
  • Paracetamol: C8H9NO2

Production of Methanol

  • Methanol (CH3OH) is the simplest alcohol.
  • Methanol production involves the destructive distillation of wood.
  • Trace amounts of methanol can be found in "Lambanog."
  • Most methanol is prepared today via catalytic hydrogenation of CO.
  • CO + 2 H₂ -> CH3OH

Production of Ethanol

  • Ethanol is the most produced alcohol.
  • Ethanol can be produced via fermentation of sugars.
  • C6H12O6 -> 2 CH3CH2OH + 2 CO2 (~95% yield)
  • For industrial purposes, ethanol is produced via acid-catalyzed hydration of ethene.
  • C2H4 + H₂O -> CH3CH2OH

Classification of Alcohols

  • Primary (1°) alcohol: The carbon atom bearing the -OH group is bonded to one other carbon.
  • Secondary (2°) alcohol: The carbon atom bearing the -OH group is bonded to two other carbons.
  • Tertiary (3°) alcohol: The carbon atom bearing the -OH group is bonded to three other carbons.
  • Aromatic alcohol: The -OH group is bonded to an aromatic hydrocarbon.
  • Phenol is not an aromatic alcohol.

Qualitative Tests of Alcohols

  • Samples for qualitative tests include 1-butanol, 2-butanol, tert-butyl alcohol, and Phenol
  • Miscibility in Water
    • 3-carbon alcohols are miscible in water.
    • Alcohols with more than 5 carbons are borderline miscible to immiscible.
  • Acidity and Basicity:
    • Acidity order: 1° alcohols > 2° alcohols > 3° alcohols
  • Lucas Test
    • Used to distinguish between 3°, 2°, and 1° alcohols based on reaction time.
    • 3° alcohol reacts in less than 3 minutes.
    • 2° alcohol reacts in 3-5 minutes.
    • 1° alcohol and Phenol show no reaction (NR).
  • Chromic Acid Test:
    • A positive reaction is indicated by the formation of a blue-green color.
      • 3° alcohol: (-)
      • 2° alcohol: (+)
      • 1° alcohol: (+)
      • Phenol: (-)
  • Iodoform Test:
    • A positive reaction results in the formation of a yellow-brown precipitate.
      • 3° alcohol: (-)
      • Phenol: (-)
      • 2° alcohol: (+)
      • 1° alcohol: (-)
  • Ferric Chloride Test:
    • Used to detect the presence of phenol, indicated by the formation of a violet solution.
      • 3° alcohol: (-)
      • 1° alcohol: (-)
      • 2° alcohol: (-) - Phenol: (+)

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