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Ch 11 - Reactions of Alcohols - R eacti ons of Alcohols 11...

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Ch 11 - Reactions of Alcohols

Ch 11 - Reactions of Alcohols - R eacti ons of Alcohols 11...

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1 1 Reactions of AlcohoLs A lcohols are important organic compounds because the hydroxyl gRoup is easily converted to almost any other functional group. In Chapter 10, we studied reac- tions that form aLcohoLs± In this chapter, we seek to uNderstand how aLcohoLs react and wH²ch reagents are best for converting them to other kinds of compounds± Table 11³1 summa´zes the types of reactions aLcohoLs undeRgo and the products that resuLtµ TABLE ±±-± Types of Reactions of Alcohols R-OH type of reaction PROduCT 0 dehydration esteRifcatIoN II ±-OH alke²es ± O-C-³' ± esteRs oxIdation ±´OH KeTo²es, aLDeµyDes¶ a·IDs tosy¸at¹o² ±´Oºs substITutio² Tosy¸ate esteRs 11-1 Oxidation States of AlcohoLs and ReLated FunctionaL Groups 460 ±´X ha¸Ides (good ¸eaving g»oUp) »eduction (I) FoRm al¼ox½de ±´H ± ±-O-±' a¸kanes ¾2) ¿ÀÁ eÂheRs Ox¶dation of alcohoLs leads to ketones, aLdehydes, and caRboxylic acidsµ These func· tional groups, in tuRn, undergo a wide variety oF additionaL reactionsµ ¸oR these rea¹ sons, alcohol oxidations are some of the most common organic reactions. ºn inorganic chemistry, we think of oxidation as a loss of eLectrons and Reduction as a gain of electrons» This pictUre woRKs well For inorganic ions, as when Cr 6 + is redUced to CR 3 + ¼ Most organic compounds are unchaRged, However, and gain oR Loss of eLectRons is not obvious± Organic chem½sts tend to think of oxidation as the ResuLt of adding an oxidizing agent (°2, Br2, etcµ), and reductIon as thE resuLt of adding a reducing agent (¾2, ¿aB¾4, etc.). Most organic chemists habituaLLy use the following simpLe rules, based on the change in the formula of the substance: OX±DAT±ON: addÀtion of ° oR 02; addition oF X2 (HaÁogens); loss oF Â2¼ REDUCT±ON: addÀtÀon of ¾2 (oR ¾ Ã )Ä Loss of ° oR 02Ä Loss oF X2» NE±THER: addition oR Áoss oF ¾ + Å ¾20, ¾X, etc» iS neÀtheR an oxÀdation nor a ReductÀonµ
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11-1 OxidatIon StaTes of AlcohoLs and ReLaTed FuncTIonaL Groups 461 H I R-C-H i H alkane no bonds to 0 H I R-C-R' I H alkane no bonds to 0 H I R-C± R' i R" alkane No bonds to 0 [0] ±0² ²³ ² H I R±C - H I H primary aLcohol o±e bond to 0 ² H ± R±C-R' i H secondary alcohol one boNd to 0 ±0] ´µ ² H i R±C-R³ i tertIary a²cohol oNe bond to 0 ³0´ ¶· o II R±C±H + H20 aldehyde Two bonds to 0 o R- -Rµ + H2 0 ketoNe two bonds ³o 0 ±0] o ±i R-C±²H carboxylIc acId tHree bonds to 0 (no ¶u·t¸e¹ oxidation) (usually no ºu¹t¸e¹ oxidation» We can telL that an oxidation or a Reduction of an aLcohoL has taken pLace by counting the numbeR of C - 0 bonds to the caRbon atom. FoR example, in a pRimary alcohol, the carbinol ( C-²H ) carbon atom has one bond to oxygen; in an aldehyde, the carbonyL carbon has two (moRe oxidized)± and in an acid, it has thRee. Oxidation of an alcohol usu- aLly converts C - H bonds to C - 0 bonds² If we conveRt an alcohoL to an aLkane, the carbinol carbon loses its bond to oxygen and gains another bond to hydRogen³ Figure 11-1
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