Ethers are prepared by the reaction of sodium alkoxides and alkyl halides. Which of the following reagents should be taken to prepare methyl tert-butyl ether?

Question

Ethers are prepared by the reaction of sodium alkoxides and alkyl halides. Which of the following reagents should be taken to prepare methyl tert-butyl ether? (A) (CH3)3C — Br + NaOCH3 (B) CH3Br + NaOC(CH3)3 (C) CH3CH2Br + NaOC(CH3)2 (D) (CH3)2C — Br + NaOCH2CH3

Tardigrade Admin · Accepted Answer

Tertiary halide can involve elimination of

H X

to give alkene in presence of a base. Hence, a tertiary alkoxide and primary alkyl halide is taken for the reaction.

C H_{3} B r + sod. t-butoxide N a OC (C H_{3})_{3} ⟶ methyl t-butyl ether C H_{3} O - C (C H_{3})_{3} + N a B r

Q. Ethers are prepared by the reaction of sodium alkoxides and alkyl halides. Which of the following reagents should be taken to prepare methyl tert-butyl ether?

$(C H_{3})_{3} C — B r + N a OC H_{3}$

$C H_{3} B r + N a OC (C H_{3})_{3}$

$C H_{3} C H_{2} B r + N a OC (C H_{3})_{2}$

$(C H_{3})_{2} C — B r + N a OC H_{2} C H_{3}$

Tertiary halide can involve elimination of $H X$ to give alkene in presence of a base. Hence, a tertiary alkoxide and primary alkyl halide is taken for the reaction.
$C H_{3} B r + sod. t-butoxide N a OC (C H_{3})_{3} ⟶ methyl t-butyl ether C H_{3} O - C (C H_{3})_{3} + N a B r$

Q. Ethers are prepared by the reaction of sodium alkoxides and alkyl halides. Which of the following reagents should be taken to prepare methyl tert-butyl ether?

(CH3​)3​C—Br+NaOCH3​

CH3​Br+NaOC(CH3​)3​

CH3​CH2​Br+NaOC(CH3​)2​

(CH3​)2​C—Br+NaOCH2​CH3​

Tertiary halide can involve elimination of HX to give alkene in presence of a base. Hence, a tertiary alkoxide and primary alkyl halide is taken for the reaction. CH3​Br+ sod. t-butoxide NaOC(CH3​)3​​⟶ methyl t-butyl ether CH3​O−C(CH3​)3​​+NaBr

$(C H_{3})_{3} C — B r + N a OC H_{3}$

$C H_{3} B r + N a OC (C H_{3})_{3}$

$C H_{3} C H_{2} B r + N a OC (C H_{3})_{2}$

$(C H_{3})_{2} C — B r + N a OC H_{2} C H_{3}$

Tertiary halide can involve elimination of $H X$ to give alkene in presence of a base. Hence, a tertiary alkoxide and primary alkyl halide is taken for the reaction.
$C H_{3} B r + sod. t-butoxide N a OC (C H_{3})_{3} ⟶ methyl t-butyl ether C H_{3} O - C (C H_{3})_{3} + N a B r$