Learning Guide for Chapter 24 - Carboxylic Acid derivatives

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LG Ch 24 p 4Nitriles are formed from the reaction of cyanides with primary alkyl haldies or tosylatesor from diazonium ions reacting with cuprous cyanide.BrNaCNOTsNaCNNH 2 HNO 2CuCNII. Physical properties of carboxylic acid derivativesEsters have low boiling points, about the same as hydrocarbons of the same molecularweight. Nitriles are similar to alcohols - the strength of the dipole attractions is similar tothe hydrogen bonding attractions of alcohols. Amides, however, are higher boiling thancarboxylic acids. Primary amides are higher than secondary amides, which are higheragain than tertiary amides because of the decreasing possibility for hydrogen bonding.OOOOCOHOHNH 2NNHHONOONH 2All carboxylic acid derivatives are soluble in organic solvents such as alcohols, ethers,chlorinated hydrocarbons, and aromatic hydrocarbons. Acid chlorides and anhydridescannot be dissolved in water because they will react with it. Some small amides, esters,and nitriles are soluble in water. Ethyl acetate, N,N-dimethylformamide, and acetonitrileare often used as reaction solvents.OOHONH 3 C C N
LG Ch 24 p 5III. Nomenclature of carboxylic acid derivativesThe names of the carboxylic acid derivatives are based on the name of the parentcarboxylic acid. The common names of formic acid and acetic acid are always used infor one and two carbon chains.All carboxylic acid derivatives are principle groups. They have less priority thancarboxylic acids, but more than aldehydes. Acid chlorides and anhydrides rarely occur inthe same compound with other functional groups, so you don't have to worry about themin the ranking. Esters and amides can be named as substituents, but it's quitecomplicated, and you won't be responsible to do so.COOH > esters / amides > nitriles > aldehydes > ketones > alcohols > aminesAcid chlorides - drop "ic acid" from the name of the parent carboxylic acid, and add"yl chloride."OClOClOClClOAcid anhydrides - change the word "acid" in the parent name to "anhydride." With mixedanhydrides, use the names of both parent acids.OOOOOOHOOOOOOOOO
Page 1 and 2: Learning Guide for Chapter 24 - Car
Page 3: Esters can be formed from carboxyli
Page 7 and 8: 3-chloro-N-methylpentanamideN-benzy
Page 9 and 10: V. Hydrolysis of carboxylic acid de
Page 11 and 12: LG Ch 24 p 11Nitriles can be hydrol
Page 13 and 14: LG Ch 24 p 13If a mixed anhydride i
Page 15 and 16: LG Ch 24 p 15Acid chlorides can be
Page 17: LG Ch 24 p 17IX. Summary of reactio

Learning Guide for Chapter 24 - Carboxylic Acid derivatives

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