H3C Br HBr H3C-C=C-CH3 c=C CH3

Introductory Chemistry: A Foundation
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Chapter20: Organic Chemistry
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Problem 1ALQ: What is meant by the term “unsaturated hydrocarbon”? What structural feature characterizes...
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Draw a complete stepwise mechanism for reaction shown below. You must show the structures of all intermediates and indicate electron flow with curly arrows.

### Chemical Reaction: Addition of HBr to 2-Butyne

**Starting Material:**
- **2-Butyne (C₄H₆)**
  - Structure: 
    - CH₃–C≡C–CH₃
  - A symmetrical alkyne with a triple bond between the central carbon atoms.

**Reagent:**
- **Hydrobromic Acid (HBr)**

**Reaction:**
- The addition of HBr to 2-butyne converts the triple bond into a double bond, resulting in the formation of a bromoalkene.

**Product:**
- **2-Bromo-2-butene (C₄H₇Br)**
  - Structure:
    - CH₃–C(Br)=C(H)–CH₃
  - The reaction produces a molecule with a double bond between carbon atoms and a bromine atom attached to one of the carbons.

In this reaction, an alkyne is transformed into an alkene by the addition of HBr, which results in the shift from a triple bond to a double bond and the addition of a bromine atom.
Transcribed Image Text:### Chemical Reaction: Addition of HBr to 2-Butyne **Starting Material:** - **2-Butyne (C₄H₆)** - Structure: - CH₃–C≡C–CH₃ - A symmetrical alkyne with a triple bond between the central carbon atoms. **Reagent:** - **Hydrobromic Acid (HBr)** **Reaction:** - The addition of HBr to 2-butyne converts the triple bond into a double bond, resulting in the formation of a bromoalkene. **Product:** - **2-Bromo-2-butene (C₄H₇Br)** - Structure: - CH₃–C(Br)=C(H)–CH₃ - The reaction produces a molecule with a double bond between carbon atoms and a bromine atom attached to one of the carbons. In this reaction, an alkyne is transformed into an alkene by the addition of HBr, which results in the shift from a triple bond to a double bond and the addition of a bromine atom.
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