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Class Note for CHEM 3332 with Professor Bean at UH


Class Note for CHEM 3332 with Professor Bean at UH

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This 10 page Class Notes was uploaded by an elite notetaker on Friday February 6, 2015. The Class Notes belongs to a course at University of Houston taught by a professor in Fall. Since its upload, it has received 21 views.

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Date Created: 02/06/15
glean 7 CHAPTER 21 CARBOXYLIC ACID DERIVATIVES acyl derivatives and nitriles alum 3 I 3 L most can be directly or indirectly prepared from RCOZH all can be hydrolyzed to RCOZH Physical Properties see section 21 3 Boiling Point in general 0 O 0 El II II R C NH2 R C OH R OH R CEN R C OR R C Cl Reactivity I lnterconversion of Derivatives Nucleophilic Acyl Substitution 3 0 3 E 3 R C Cl R C O C R R C OR R C NHZ Order of reactivity results from a combination of factors 1 Basicity stability of the leaving group 3 Cl 0 C R OR NH2 2 Resonance stabilization in derivative or How is the carbonyl carbon the more the more reactive 9 3 3 9 S R C Cl R C O C R R C OR R C NH2 3 Steric factors consider when comparing different compounds of the same derivative OR quotOR gtknOR O O O Naming Carboxylic Acid Derivatives From Carboxylic Acid Names drop quotic aci quot add quotylhalidequot or drop quotcarboxylic aci quot add quotcarbonyl halidequot o 0 I a gt CHSC H a c I lt2 O a 7 II Anhydrides Symmetrical drop quotacidquot add quotanhydridequot 0 9 9 O 39 H CHfHZCOCCHLCH3 Ctsc c o ccl Unsymmetrical name both acids composing the anhydride omit each aquot acidquot and add quotanhydridequot 9 O i u I III Esters Writen as name of alkyl group attached to 0 plus acid name drop quotic aci quot add quotatequot 0 n K C oR C H E I I C 3 2 0 LCH3 Cr C o cu tug1 045 P 3 O cqzeH Q43 IV Amides Unsubstituted NH2 replace quoticoic acidquot with quot quotamidequot or quotcarboxylic acidquot with quotcarboxamidequot O OQQ NH n 2 943 CH3 CHLCHLC O u CHZCNH2 c143 Substituted NHR or NR2 writen as name of substituent bonded to nitrogen pre ceeded by quotEquot followed by amide name formed as above o 39u O CH CH lt1 u 3 Z NHLHZCH3 CLL3IHCHZCNCHJ7 C H 3 C 3 V Nim39les Add quotnitr equot to corresponding IUPAC alkane name or for alkanecarboxylic acids replace quotcarboxylic acidquot with quotcarbonitrilequot O C CN H CH3CH1CHCHZCHZC39E N O CHSC CHZ CN C l39 Nitrile name39derived from an acid39s common name drop quotic or oic ac1dquot and add quotonitrilequot 7076 CE As a substituent name as a cyano group F f 39 0 P cuBCH CHLCHZCOH CH3CH CHLCKNHZ Synthesis and Reactions of Acid Chlorides RCOCI O R 3 OH 39 1 R39MgX or R39Li RZCULI 2 H3O O 2 Q R c lt R39M X R L39 AC3 Cl 9 or 39 gt 1 LiAH4 H20 2 H30 LiAIHOtBu3 or II NH3 R39CO39 Na or RNH2 or R2NH Example Mechanisms Synthesis and Reactions of Anhydrides 3 R C AICI3 Example Mechanism 0 3 ll move R m Cyclic Anhydrides 8 H 0 OH HEAT gt C OH H 9 0 Example 0 CE O gt OH NaOH R C O Synthesis and Reactions of Esters O o quot3 n R CI R COH RIOI R39OH H if H 0 Hi or OH R COR Rquotng or RquotLi 1 LiAlH4 RquotOH H H30 NH3 or RIINH2 1 DIBAH or Rquot2NH 2 H30 Cyclic Esters 0 II H H39O39CHchZCHZ39C gt OH Saponification 3 NaOH39 393 El R C R IZ OH OR39 OR39 1 RquotMg 2 H3O or R39Li Synthesis and Reactions of Amides Few reactions fortunately PM 5 2 0 T3 ll NH2CHC NHCHC NHCHCOH O Q NH3 II mg or RNH2 RCNRz cu or Rg NH f R CNHR HZOlieat RCNH2 POCI3 0 SOCI2 or P205 gt H or OH 1 LiAIH4 Br2 0 2 H20 OI39 H3O Reduction of Amide to Amine 0 II RCNH2 H AIH3 Ll 0 Ni 1 LiAH4 gt 2 H20 OI H30 Dehydration to Nitrile 1 amide only 0 0 II R C39NHZ Cl S CI 0 ll CH3CH2 CNH2 04 Synthesis and Reactions of Nitriles I R x R CNH2 NaCN POC3 or SOCI2 or P205 1 R39 X H20Heat RC EN Ma H or 390H 2 H30 1 LiAIH4 2 H20 or H30 or H2 Pt or Ni Hydrolysis basic conditions O H O H CN 39 I 0H R RCN RCN Reduction to Amine MEN H AIH339 Li Examples 1 CHaCHgCEN NaOH I Heat 2 CH30H2CEN 1 LiAlH4 2 H20 or H30 or H2Pt or Ni 1 CHaCHgMgBr CH E 3 3CH2 C N 2 H30 Spectroscopy Summary of Carboxylic Acid Derivatives O 0 II c stretch IR 0 carbon 30 NMR other 0 R E cr 1800 1775 cm391 170 ppm 3 lt3 1800 cm391 R C O C R 1750 cm391 170 ppm 0 ll 3 0 03 1735 cm391 170 180 ppm IOI 1 IR NH stretch RCNH2 1640 1680 cm 180 ppm 32003500 cm1 1 2 peaks 2 1 peak 3 no peak 1H NMR N 59 0 often broad D20 exchangeable RCEN IR GEN stretch 2200 cmquot sharp medium Example 7 CeHstO 39 W 2800 2400 20001300 CGHISNO 1 W 1400 cmquot TY fl xlrr 39 35 32 515 L 10 0905 Chemical shift ppm 39 W BrN a ioc CGHBNO 2800 2400 2000 1800 cmquot 19 33957 H00 I235 775 C6H15NO 7739 T 7quot fl V 39 T I 7 V 33 32 315 11 10 096 TMS 10 9 a 7 6 s 4 5 05 Chemical shift ppm 1 O


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