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)
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
![**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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8f2ba725-83de-43a2-959b-aa0d30d09f08%2F7ed90a8d-24f4-4528-a388-ef9450ae63ac%2Fcsmk0xk_processed.jpeg&w=3840&q=75)
![**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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8f2ba725-83de-43a2-959b-aa0d30d09f08%2F7ed90a8d-24f4-4528-a388-ef9450ae63ac%2F98szyff_processed.jpeg&w=3840&q=75)
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