Chapter_10_(Wade)

Chapter_10_(Wade) - Grignard, R-MgBr, (or organometallic,...

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ORGANIC CHEMISTRY LANEY COLLEGE CHEM 12A INSTRUCTOR: S. CORLETT Chapter 10 Learning Objectives and Terminology (Wade) Name alcohols using IUPAC (alkane + -ol) and common names (alkyl alcohol). If the OH group is a substituent, then it is called a hydroxy group Physical properties such as boiling point are dominated by the strength of hydrogen bonding. The regular acidity of alcohols (p K a 16-18) is similar to water (p K a 15.7) Know the acidity of neutral alcohols and protonated alcohols (which is like the hydronium ion). Which alcohols are stronger bases? The amount of inductive vs. resonance stability of the conjugate base (alkoxides) usually determines the acid strength of the alcohol. The common preparations of alcohols are: 1. from alkenes: hydroboration or oxymercuration osmylation (cis-1,2-dihydroxylation) epoxidation followed by hydrolysis (over anti 1,2-dihydroxylation) 2. from carbonyl compounds:
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Unformatted text preview: Grignard, R-MgBr, (or organometallic, R-M) additions or hydride reduction Many examples for the Grignard reactionadditions to aldehydes, ketones, esters, and acid chlorides, but all have a common mechanism for the first step; the latter cases each have a leaving group so a second addition of the organometallic can occur. Also Grignard reagents add to epoxides to yield alcohols. 3. from nucleophilic substitution reactions, S N 1 or S N 2 (more common). Reduction of carbonyl compounds gives alcohols. The two common reducing reagents are both hydride reagents, NaBH 4 and LiAlH 4 . NaBH 4 is a mild reducing reagent and only reduces aldehydes and ketones. LiAlH 4 reduces all carbonyl compounds. Thiols have many similarities to alcohols, but are appreciable more acidic (p K a 9). Oxidation of thiols can lead to sulfonic acids or disulfides depending on the oxidant....
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