Learning Group Problem 2 Consider the following sequence of reactions, taken from the early steps in a synthesis of w-fluorooleic acid, a toxic natural compound from an African shrub, (w-fluorooleic adid, also called "ratsbane," has been used to kill rats and also as an arrow poison in tribal warfare). (i) 1-Bromo-8-Auorooctane + sodium acetylide (the sodium salt of ethyne) compound A (C10H17F) (ii) CompoundA + NANH2 compound B (C10H16FNA). (iii) Compound B +1-(CH),-C compound C (C,7H30CIF) (iv) Compound C + NaCN compound D (C,HNF)

Chemistry: Matter and Change
1st Edition
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Chapter8: Covalent Bonding
Section: Chapter Questions
Problem 134A
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**Chemical Drawing Exercise**

**Instructions:**

1. **Draw Compound B**
   - Note: Do not include lone pairs in your drawings, but drawings must include counter ions.

   ![Image showing a linear chemical compound with a fluorine (F) atom at one end and a hydrogen (H) atom at the other. It consists of a zigzag line structure with multiple bonds, including a triple bond near the hydrogen.]

2. **Feedback:**
   - Your answer is incorrect. Try again.

3. **Draw Compound C**
   - A placeholder exists for drawing compound C, with an option to edit.

4. **Feedback:**
   - Your answer is incorrect. Try again.

5. **Draw Compound D**
   - Another placeholder for drawing compound D, with an option to edit.

**Note:** Pay attention to the structural details and ensure correct bond representation when drawing each compound.
Transcribed Image Text:**Chemical Drawing Exercise** **Instructions:** 1. **Draw Compound B** - Note: Do not include lone pairs in your drawings, but drawings must include counter ions. ![Image showing a linear chemical compound with a fluorine (F) atom at one end and a hydrogen (H) atom at the other. It consists of a zigzag line structure with multiple bonds, including a triple bond near the hydrogen.] 2. **Feedback:** - Your answer is incorrect. Try again. 3. **Draw Compound C** - A placeholder exists for drawing compound C, with an option to edit. 4. **Feedback:** - Your answer is incorrect. Try again. 5. **Draw Compound D** - Another placeholder for drawing compound D, with an option to edit. **Note:** Pay attention to the structural details and ensure correct bond representation when drawing each compound.
**Title: Learning Group Problem 2**

**Objective:** Explore the sequence of reactions involved in the synthesis of ω-fluorooleic acid, a toxic natural compound from an African shrub known as "ratsbane."

**Reaction Sequence:**

1. **(i)** **1-Bromo-8-fluorooctane + Sodium Acetylide (the sodium salt of ethyne) → Compound A (C₁₀H₁₆FNa)**
2. **(ii)** **Compound A + NaNH₂ → Compound B (C₁₀H₁₇FNa)**
3. **(iii)** **Compound B + I—(CH₂)₇—Cl → Compound C (C₁₇H₃₀ClF)**
4. **(iv)** **Compound C + NaCN → Compound D (C₁₈H₃₀NF)**

**Task:**
The image shows an incorrect attempt at drawing **Compound A**. The structure provided needs revision.

**Structure of Compound A:**
- The structure provided shows a carbon chain with a fluorine (F) atom attached at the end.

**Note:** Guidance for drawing molecular structures and understanding organic synthesis reactions is provided.

**Help Section:**
For further assistance, explore resources on Molecular Drawing questions.

**Version:** 4.24.2020
Transcribed Image Text:**Title: Learning Group Problem 2** **Objective:** Explore the sequence of reactions involved in the synthesis of ω-fluorooleic acid, a toxic natural compound from an African shrub known as "ratsbane." **Reaction Sequence:** 1. **(i)** **1-Bromo-8-fluorooctane + Sodium Acetylide (the sodium salt of ethyne) → Compound A (C₁₀H₁₆FNa)** 2. **(ii)** **Compound A + NaNH₂ → Compound B (C₁₀H₁₇FNa)** 3. **(iii)** **Compound B + I—(CH₂)₇—Cl → Compound C (C₁₇H₃₀ClF)** 4. **(iv)** **Compound C + NaCN → Compound D (C₁₈H₃₀NF)** **Task:** The image shows an incorrect attempt at drawing **Compound A**. The structure provided needs revision. **Structure of Compound A:** - The structure provided shows a carbon chain with a fluorine (F) atom attached at the end. **Note:** Guidance for drawing molecular structures and understanding organic synthesis reactions is provided. **Help Section:** For further assistance, explore resources on Molecular Drawing questions. **Version:** 4.24.2020
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