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Published on : Dec 09, 2014
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Slide 1 - Alcohols
Slide 2 - Hydrogen Bonding Three ethanol molecules.
Slide 3 - Hydrogen Bonding & boiling point Increases boiling point, higher temperature needed to separate the molecules. Hexane 69 deg. 1-pentanol 138 1,4-butanediol 230 Ethanol 78 deg Dimethyl ether 24
Slide 4 - Earlier Discussion of Acidity Methanol Ethanol 2-Propanol 2-Methyl-2-propanol RO-H  RO – (solvated) + H + (solvated) Increasing Acidity of the alcohol Recall: H2O + Na Na+ + OH- + ½ H2(g) Alcohols behave similarly ROH + Na Na+ + OR- + ½ H2(g) Alkoxide, strong base, strong nucleophile (unless sterically hindered) Also: ROH + NaH Na+ + OR- + ½ H2(g) Increasing Basicity of Alkoxide Anion, the conjugate base Alkoxide ion, base Alkoxides can be produced in several ways…
Slide 5 - -OH as a Leaving Group R-OH + H +  R-OH2+ Protonation of the alcohol sets-up a good leaving group, water. Poor leaving group, hydroxide ion. Another way to turn the –OH into a leaving group…
Slide 6 - Conversion to Alkyl Halide, HX + ROH  RX + H2O When a carbocation can be formed (Tertiary, Secondary alcohols) beware of rearangement. SN1 Expect both configurations. When a carbocation cannot be formed. Methanol, primary. SN2
Slide 7 - But sometimes experiment does not agree with our ideas… Observed reaction The problem: Rearrangement of carbon skeleton which usually indicates carbocations. Reacting alcohol is primary; do not expect carbocation. Time to adjust our thinking a bit…. Not a primary carbocation
Slide 8 - Other ways to convert: ROH  RX We have used acid to convert OH into a good leaving group There are other ways to accomplish the conversion to the halide. Leaving group. Leaving group. Next, a very useful alternative to halide…
Slide 9 - An alternative to making the halide: ROH  ROTs p-toluenesulfonyl chloride Tosyl chloride TsCl Tosylate group, -OTs, good leaving group, including the oxygen. The configuration of the R group is unchanged. Preparation from alcohols.
Slide 10 - Example Preparation of tosylate. Retention of configuration
Slide 11 - Substitution on a tosylate The –OTs group is an excellent leaving group
Slide 12 - Acid Catalyzed Dehydration of an Alcohol, discussed earlier as reverse of hydration Protonation, establishing of good leaving group. Elimination of water to yield carbocation in rate determining step. Expect tertiary faster than secondary. Rearrangements can occur. Elimination of H+ from carbocation to yield alkene. Zaitsev Rule followed. Secondary and tertiary alcohols, carbocations
Slide 13 - Primary alcohols Problem: primary carbocations are not observed. Need a modified, non-carbocation mechanism. Recall these concepts: Nucleophilic substitution on tertiary halides invokes the carbocation but nucleophilic substitution on primary RX avoids the carbocation by requiring the nucleophile to become involved immediately. The E2 reaction requires the strong base to become involved immediately. Note that secondary and tertiary protonated alcohols eliminate the water to yield a carbocation because the carbocation is relatively stable. The carbocation then undergoes a second step: removal of the H+. The primary carbocation is too unstable for our liking so we combine the departure of the water with the removal of the H+. What would the mechanism be???
Slide 14 - Here is the mechanism for acid catalyzed dehydration of Primary alcohols 1. protonation 2. The carbocation is avoided by removing the H at the same time as H2O departs (like E2). As before, rearrangements can be done while avoiding the primary carbocation.
Slide 15 - Principle of Microscopic Reversibility Same mechanism in either direction.
Slide 16 - Pinacol Rearrangement: an example of stabilization of a carbocation by an adjacent lone pair. Overall:
Slide 17 - Mechanism Reversible protonation. Elimination of water to yield tertiary carbocation. 1,2 rearrangement to yield resonance stabilized cation. Deprotonation. This is a protonated ketone!
Slide 18 - Oxidation Primary alcohol RCH2OH RCH=O RCO2H Na2Cr2O7 Na2Cr2O7 Na2Cr2O7 (orange)  Cr3+ (green) Actual reagent is H2CrO4, chromic acid. Secondary R2CHOH R2C=O Tertiary R3COH NR KMnO4 (basic) can also be used. MnO2 is produced. The failure of an attempted oxidation (no color change) is evidence for a tertiary alcohol. Na2Cr2O7
Slide 19 - Example…
Slide 20 - Oxidation using PCC Primary alcohol RCH2OH RCH=O PCC PCC Secondary R2CHOH R2C=O Stops here, is not oxidized to carboxylic acid
Slide 21 - Periodic Acid Oxidation
Slide 22 - Mechanistic Notes Cyclic structure is formed during the reaction. Evidence of cyclic intermediate.
Slide 23 - Sulfur Analogs, Thiols Preparation RI + HS-  RSH SN2 reaction. Best for primary, ok secondary, not tertiary (E2 instead) Acidity H2S pKa = 7.0 RSH pKa = 8.5 Oxidation