Study Guides/Chemistry/tert-Butyl Alcohol
Study Guide · Chemistry

Structure and Uses of tert-Butyl Alcohol

In Organic Chemistry, alcohols are classified into primary, secondary, and tertiary based on the carbon atom to which the hydroxyl (-OH) group is attached. tert-Butyl alcohol (TBA) is the simplest example of a tertiary alcohol.

Question (Click to Flip)

Why is tert-butyl alcohol solid at room temperature on cold days?

Answer

Its melting point is unusually high for a small alcohol, at exactly 25.69 °C (78.2 °F). So, if the room temperature drops below 25°C, the liquid will freeze into a white solid inside its bottle.

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Key Facts

Unlike primary and secondary alcohols, tert-butyl alcohol cannot be oxidized easily by normal oxidizing agents (like Potassium Dichromate) because there are no hydrogen atoms attached to the tertiary carbon.

Chemical Formula and Structure

  • Chemical Formula: C₄H₁₀O (or (CH₃)₃COH).
  • Structure: It features a central carbon atom that is directly bonded to three other methyl (-CH₃) groups and one hydroxyl (-OH) group. Because the carbon holding the -OH group is bonded to three other carbons, it is a tertiary (3°) alcohol.

IUPAC Name

While 'tert-butyl alcohol' is its common, widely accepted name, its official IUPAC name is 2-Methylpropan-2-ol.

How do we get this name?

  1. Find the longest carbon chain containing the -OH group. Here, the longest chain is 3 carbons long (Propane).
  2. The -OH group is on the 2nd carbon (propan-2-ol).
  3. There is a methyl group attached to the 2nd carbon (2-methyl).

Properties and Uses

  • Physical State: At room temperature, TBA is a colorless liquid (or a white solid if the room is below 25°C), with a strong camphor-like odor.
  • Solubility: It is highly miscible (mixes easily) with water.
  • Uses: It is primarily used as a solvent in paint removers, a denaturant for ethanol, and an intermediate in the production of fuel additives (like MTBE) to reduce engine knocking.

Questions and Answers

Why is tert-butyl alcohol solid at room temperature on cold days?+

Its melting point is unusually high for a small alcohol, at exactly **25.69 °C (78.2 °F)**. So, if the room temperature drops below 25°C, the liquid will freeze into a white solid inside its bottle.

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