chapter 13: ethers & epoxides

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Last updated 7:39 PM on 8/31/26
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9 Terms

1
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Williamson ether synthesis

reagents: 1) NaH 2) RX SN2 rxn ~ build an ether bridge between 2 groups

<p>reagents: 1) NaH 2) RX SN2 rxn ~ build an ether bridge between 2 groups</p>
2
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Alkoxymercuration-Demercuration

reagents: 1) Hg(OAc)2 2) NaBH4 This reaction involves the addition of an alkoxy group to an alkene and is followed by reduction to yield an ether.

<p>reagents: 1) Hg(OAc)<sub><sup>2</sup></sub> 2) NaBH4 This reaction involves the addition of an alkoxy group to an alkene and is followed by reduction to yield an ether. </p>
3
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Acidic cleavage

reagents: xs HX/heat ether couple is broken up by acid, if one partner is an aryl group it keeps the alcohol

<p>reagents: xs HX/heat ether couple is broken up by acid, if one partner is an aryl group it keeps the alcohol </p>
4
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Autooxidation

reagents: O2 (slow), ether becomes hydroperoxide

<p>reagents: O<sub>2</sub> (slow), ether becomes hydroperoxide </p>
5
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preparation of epoxides

reagents: MCPBA (concerted) alkene —> epoxide

1) Br2, H2O 2) NaOH (stepwise) halohydrin—> epoxide

<p>reagents: MCPBA (concerted) alkene —&gt; epoxide</p><p> 1) Br<sub>2</sub>, H<sub>2</sub>O 2) NaOH (stepwise) halohydrin—&gt; epoxide </p>
6
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Ring opening reactions

Strong nuc: NaCN, NaOR, NaSR, RMgBr, LiAlH(LAH)~ attacks the less substituted carbon

Acid catalyzed: HX, [H+]/H2O, [H+]/ ROH

<p>Strong nuc: NaCN, NaOR, NaSR, RMgBr, LiAlH(LAH)~ attacks the less substituted carbon </p><p>Acid catalyzed: HX, [H<sup>+</sup>]/H<sub>2</sub>O, [H<sup>+</sup>]/ ROH</p>
7
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Thiols

reagents: NaSH (SN2)

NaOH/H2O , Br2 (RSH + RSH —> disulfide)

HCl, Zn (disulfide —> RSH + RSH)

<p>reagents: NaSH (SN2) </p><p>NaOH/H<sub>2</sub>O , Br<sub>2</sub> (RSH + RSH —&gt; disulfide) </p><p>HCl, Zn (disulfide —&gt; RSH + RSH) </p>
8
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Sulfides

reagents: 1)NaOH 2)RX (R-S-H—>R-S-R)


sulfide NaIO4 sulfoxide H2O2 sulfone

<p>reagents: 1)NaOH 2)RX (R-S-H—&gt;R-S-R)</p><p></p><p>sulfide <u>NaIO<sub>4</sub></u><sub> </sub>sulfoxide <u>H<sub>2</sub>O<sub>2</sub></u> sulfone</p>
9
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enantioselective epoxidation

reagents: (CH3)3COOH, Ti(OiPr)4 +DET alkene—> epoxide with R on dash and alcohol on solid

(CH3)3COOH, Ti(OiPr)4 -DET alkene—> epoxide with R on solid and alcohol on dashed

<p>reagents: (CH<sub>3</sub>)<sub>3</sub>COOH, Ti(OiPr)<sub>4</sub> +DET alkene—&gt; epoxide with R on dash and alcohol on solid </p><p>(CH<sub>3</sub>)<sub>3</sub>COOH, Ti(OiPr)<sub>4</sub> -DET alkene—&gt; epoxide with R on solid and alcohol on dashed</p>