UH CHEM 3331 - reactions of alcohols continued (3 pages)

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reactions of alcohols continued



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reactions of alcohols continued

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Lecture number:
25
Pages:
3
Type:
Lecture Note
School:
University of Houston
Course:
Chem 3331 - Organic Chemistry
Edition:
1
Documents in this Packet

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CHEM 3331 1nd Edition Lecture 25 Outline of Last Lecture I Oxidation II Biological oxidation III Formation of sulfonate esters IV Reduction of alcohols V Reactions of alcohols with HX Outline of Current Lecture I Reactions with PX3 or PX5 II Reaction with thionyl chloride III Dehydration IV Reactions of diols V Formation of esters Current Lecture I Reactions with PX3 or PX5 We have already seen ROH HX RX H2O 3ROH PCl3 PBr3 H3PO3 RCl Br and 6ROH 2P 3I2 6RI 2H3PO3 This works well with primary and secondary alcohols but due to their steric bulk it is best to use HX for tertiary These reactions also create a liquid side product H3PO3 II Reaction with thionyl chloride To eliminate any side products being formed we use thionyl chloride SOCl2 ROH SOCl2 RCl SO2 HCl The two byproducts are gases so they escape into the air leaving behind only the RCl These notes represent a detailed interpretation of the professor s lecture GradeBuddy is best used as a supplement to your own notes not as a substitute III Dehydration ROH H3O ROH2 H2O R 2C C R 2 When H3O is introduced it adds a hydrogen to the existing alcohol making OH2 This gives a positive charge to the oxygen so it leaves leaving behind a positive charge on the carbon When the remaining H2O is reintroduced the adjacent hydrogen atom is swept up by it and allows for a double bond to form connecting to the positive charge Thus creating an alkene This is an E1 reaction ROH H ROH2 ROH RO H R H ROR 2ROH H H2O ROR 2 molecules 2 molecules this reaction is not temperature dependent ROH H ROR alkene 1 molecule 2 molecules this reaction is temperature dependent so you will form more products with a higher temperature IV Reactions of diols An example of this would be the pinacol rearrangement From CH3 2COHCOH CH3 2 to CH2C OC CH3 3 Another example is the use of HIO4 on a diol it creates double bonds onto oxygen opening the ring up It is similar to ozonolysis on an alkene V Formation of esters Esters contain a double bond to an oxygen



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