chapter 11(1)

chapter 11(1) - Start of Chapter 11 Overview for the...

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Start of Chapter 11
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Alcohol ROH Alkyl halides RX Esters Carboxylic acids Ethers ROR Ketones aldehydes alkenes R OH O R R O R H O R OR O R PBr 3 , SOCl 2 NaOH H + , H 2 O H + , H 2 O Overview for the Reactions of Alcohols
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Reactivity of alcohols An alcohol is a weak nucleophile: R-OH The deprotonated version, alkoxide ion is a strong nucleophile: R-O - Occurs when an alcohol is reacted with Na or K metal or NaH What about the hydroxyl as a leaving group? The hydroxyl group would leave as a STONG BASE Which is too reactive to be considered a good leaving group
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Alcohols are acidic R-O-H + B: RO - + BH Factors that effect acidity: substituents on the alkyl group - electron-withdrawing atom - Presence of double bonds - Degree of substitution Electronegative atoms that are closest to the hydroxyl increase acidity A primary hydroxyl is more acidic than a tertiary hydroxyl - Resonance increases the acidity of a hydroxyl the negative charge can spread out through resonance then the more stable that alkoxide ion is - Acidity of phenol is increased by the presence of an electron withdrawing group such as a halogen ortho- or para to the –OH & decreased by the presence of an electron-donating group such as a methyl or another hydroxyl
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Deprotonating an alcohol produces and alkoxide ion Methanol + Na (metal) t -butyl alcohol + K (metal) OH + NaOH H 3 C O Na O K O Na
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OH Na or 2K O K + + H 2 OH O Na + + H 2 NaH OH O Na + + NH
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chapter 11(1) - Start of Chapter 11 Overview for the...

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