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Question: $\qquad CH_2-CH_2 \xrightarrow{xNaNH_2}$ $\qquad | \qquad |$ $\qquad Cl \qquad Cl$ ...

CH2CH2xNaNH2\qquad CH_2-CH_2 \xrightarrow{xNaNH_2} \qquad | \qquad | ClCl\qquad Cl \qquad Cl

Answer

Acetylene (Ethyne)

Explanation

Solution

Given the molecule

ClClCH2CH2\begin{array}{r} \text{Cl} \quad \quad \text{Cl} \\ | \quad \quad | \\ CH_2-CH_2 \end{array}

this is 1,2-dichloroethane. When treated with excess NaNH2NaNH_2, a strong base, two successive E2 eliminations occur (first forming a vinyl chloride intermediate and then an alkyne), ultimately yielding acetylene (ethyne).

Reaction:

ClCH2-CH2ClxNaNH2HCCH\text{ClCH}_2\text{-CH}_2\text{Cl} \xrightarrow{x \,\text{NaNH}_2} \text{HC}\equiv \text{CH}

Excess NaNH2NaNH_2 deprotonates twice, eliminating two HClHCl molecules from 1,2-dichloroethane to form acetylene.