An alkane with the molecular formula C3H18 forms only one monochlorinated product when heated with Cl2 . Propose a structure for the alkane. 1.

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**Organic Chemistry Practice Problems**

1. **Problem 1: Alkane Structure Determination**
   - An alkane with the molecular formula C<sub>5</sub>H<sub>12</sub> forms only one monochlorinated product when heated with Cl<sub>2</sub>. Propose a structure for the alkane.

2. **Problem 2: Reaction Rate with Bromine**
   - Arrange the following in order of increasing rate of reaction with Br<sub>2</sub> and UV light:
     - (a) CH<sub>3</sub>CH=CHCH<sub>3</sub>
     - (b) (CH<sub>3</sub>)<sub>3</sub>CC(CH<sub>3</sub>)<sub>3</sub>
     - (c) (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CH
     - (d) (CH<sub>3</sub>)<sub>3</sub>CH
   - Answer format: least reactive to most reactive

3. **Problem 3: Monochlorinated Products**
   - How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl<sub>2</sub>?
     - [Cyclobutane diagram]
   - Options:
     - A) 2
     - B) 4
     - C) 5
     - D) 6
     - E) 8

4. **Problem 4: Reaction Mechanism Analysis**
   - The reaction Br<sub>2</sub> + CH<sub>3</sub>Br → CH<sub>2</sub>Br<sub>2</sub> + HBr was carried out. Which of the following mechanism steps is both productive and relatively likely to occur?
     - A) Br · + CH<sub>2</sub>Br → CH<sub>2</sub>Br<sub>2</sub>
     - B) Br · + CH<sub>3</sub> → CH<sub>3</sub>Br
     - C) Br · + Br<sub>2</sub> → Br<sub>2</sub> + Br ·
     - D) Br · + CH
Transcribed Image Text:**Organic Chemistry Practice Problems** 1. **Problem 1: Alkane Structure Determination** - An alkane with the molecular formula C<sub>5</sub>H<sub>12</sub> forms only one monochlorinated product when heated with Cl<sub>2</sub>. Propose a structure for the alkane. 2. **Problem 2: Reaction Rate with Bromine** - Arrange the following in order of increasing rate of reaction with Br<sub>2</sub> and UV light: - (a) CH<sub>3</sub>CH=CHCH<sub>3</sub> - (b) (CH<sub>3</sub>)<sub>3</sub>CC(CH<sub>3</sub>)<sub>3</sub> - (c) (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CH - (d) (CH<sub>3</sub>)<sub>3</sub>CH - Answer format: least reactive to most reactive 3. **Problem 3: Monochlorinated Products** - How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl<sub>2</sub>? - [Cyclobutane diagram] - Options: - A) 2 - B) 4 - C) 5 - D) 6 - E) 8 4. **Problem 4: Reaction Mechanism Analysis** - The reaction Br<sub>2</sub> + CH<sub>3</sub>Br → CH<sub>2</sub>Br<sub>2</sub> + HBr was carried out. Which of the following mechanism steps is both productive and relatively likely to occur? - A) Br · + CH<sub>2</sub>Br → CH<sub>2</sub>Br<sub>2</sub> - B) Br · + CH<sub>3</sub> → CH<sub>3</sub>Br - C) Br · + Br<sub>2</sub> → Br<sub>2</sub> + Br · - D) Br · + CH
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