Help eclipsed. C. Label any/all steric strain. D. Draw an energy diagram ranking the relative energy of each Newman projection as you move through the full 360 rotation. 11

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### CHEM 2251: Problem Set 4

#### Problem 4

**Task:** Draw the structure of 1,1-dibromo-2-methylpropane.

1. **Looking down the C1–C2 bond**, draw a Newman projection. Then, by rotating that bond 60 degrees at a time, **draw the 5 remaining Newman projections**.
2. **Label each Newman projection** as staggered or eclipsed.
3. Label any/all **steric strain**.
4. **Draw an energy diagram** ranking the relative energy of each Newman projection as you move through the full 360-degree rotation.

---

**Newman Projections of 1,1-dibromo-2-methylpropane**

1. **Structure:**
   - The given formula outlines the positions of Br, H, and CH3 groups as:
     ```
       Br          CH3
       |           |
    Br-C1         C3
       |           |
     H-C2-H     H-C3-H
     ```

2. **Newman Projections:**

   i. **Projection 1: Staggered**
   - Front carbon (C1): Br, H, H
   - Rear carbon (C2): CH3, Br, H
     ```
       H     Br     CH3
       /       |       \
      Br — C1 — C2 — CH3
       \       |       /
        H     H     Br
       (Drawing: Front carbon in the circle, rear groups staggered)
     ```

   ii. **Projection 2: Eclipsed (60° rotation)**
   - Front carbon (C1): Br, H, H
   - Rear carbon (C2): CH3, H, Br
     ```
       Br    Br    H
       /       |       \
      H — C1 — C2 — H
       \       |       /
        H     CH3   CH3
       (Drawing: Front carbon in the circle, rear groups eclipsed)
     ```

   iii. **Projection 3: Staggered (60° further rotation)**
   - Front carbon (C1): Br, H, H
   - Rear carbon (C2): Br, CH3, H
     ```
       H     CH3     Br
       /       |       \
      Br — C1 — C
Transcribed Image Text:### CHEM 2251: Problem Set 4 #### Problem 4 **Task:** Draw the structure of 1,1-dibromo-2-methylpropane. 1. **Looking down the C1–C2 bond**, draw a Newman projection. Then, by rotating that bond 60 degrees at a time, **draw the 5 remaining Newman projections**. 2. **Label each Newman projection** as staggered or eclipsed. 3. Label any/all **steric strain**. 4. **Draw an energy diagram** ranking the relative energy of each Newman projection as you move through the full 360-degree rotation. --- **Newman Projections of 1,1-dibromo-2-methylpropane** 1. **Structure:** - The given formula outlines the positions of Br, H, and CH3 groups as: ``` Br CH3 | | Br-C1 C3 | | H-C2-H H-C3-H ``` 2. **Newman Projections:** i. **Projection 1: Staggered** - Front carbon (C1): Br, H, H - Rear carbon (C2): CH3, Br, H ``` H Br CH3 / | \ Br — C1 — C2 — CH3 \ | / H H Br (Drawing: Front carbon in the circle, rear groups staggered) ``` ii. **Projection 2: Eclipsed (60° rotation)** - Front carbon (C1): Br, H, H - Rear carbon (C2): CH3, H, Br ``` Br Br H / | \ H — C1 — C2 — H \ | / H CH3 CH3 (Drawing: Front carbon in the circle, rear groups eclipsed) ``` iii. **Projection 3: Staggered (60° further rotation)** - Front carbon (C1): Br, H, H - Rear carbon (C2): Br, CH3, H ``` H CH3 Br / | \ Br — C1 — C
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