Which of the following best explains why the synthetic route shown below would be unsuccessful? 1) CH;CH,Br HCEC: CH;CH,C=CC(CH3)a 2) NANH2 3) (CH3)3CBr O Reaction with sodium amide will result in formation of a primary alkyne O The alkynide anion formed by reaction with sodium amide will facilitate an E2 (rather than SN2) reaction with t-butyl bromide O The alkynide anion is not a strong enough nucleophile to react with 1-bromopropane in step 1 Sodium amide is not a strong enough base to deprotonate the terminal alkyne in step 2 O Both substitution reactions will occur on the same end of the alkyne, making a product different than the one shown

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Chapter1: Chemical Foundations
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**Question:**

**Which of the following best explains why the synthetic route shown below would be unsuccessful?**

\[ \text{HC} \equiv \text{C}^- \]
\[ \begin{array}{lll}
\quad \quad \quad \quad & 1) \quad \text{CH}_3\text{CH}_2\text{Br} & \\
\quad \quad \quad \quad & \quad 2) \quad \text{NaNH}_2 & \quad \longrightarrow \quad \text{CH}_3\text{CH}_2\text{C} \equiv \text{CC}(\text{CH}_3)_3 \\
\quad \quad \quad \quad & 3) \quad (\text{CH}_3)_3\text{CBr} & 
\end{array} \]

**Options:**

- \( \circ \) Reaction with sodium amide will result in formation of a primary alkyne
- \( \circ \) The alkynide anion formed by reaction with sodium amide will facilitate an E2 (rather than SN2) reaction with t-butyl bromide
- \( \circ \) The alkynide anion is not a strong enough nucleophile to react with 1-bromopropane in step 1
- \( \circ \) Sodium amide is not a strong enough base to deprotonate the terminal alkyne in step 2
- \( \circ \) Both substitution reactions will occur on the same end of the alkyne, making a product different than the one shown
Transcribed Image Text:**Question:** **Which of the following best explains why the synthetic route shown below would be unsuccessful?** \[ \text{HC} \equiv \text{C}^- \] \[ \begin{array}{lll} \quad \quad \quad \quad & 1) \quad \text{CH}_3\text{CH}_2\text{Br} & \\ \quad \quad \quad \quad & \quad 2) \quad \text{NaNH}_2 & \quad \longrightarrow \quad \text{CH}_3\text{CH}_2\text{C} \equiv \text{CC}(\text{CH}_3)_3 \\ \quad \quad \quad \quad & 3) \quad (\text{CH}_3)_3\text{CBr} & \end{array} \] **Options:** - \( \circ \) Reaction with sodium amide will result in formation of a primary alkyne - \( \circ \) The alkynide anion formed by reaction with sodium amide will facilitate an E2 (rather than SN2) reaction with t-butyl bromide - \( \circ \) The alkynide anion is not a strong enough nucleophile to react with 1-bromopropane in step 1 - \( \circ \) Sodium amide is not a strong enough base to deprotonate the terminal alkyne in step 2 - \( \circ \) Both substitution reactions will occur on the same end of the alkyne, making a product different than the one shown
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