Chapter 10. Carboxylic Acids and Derivatives. Naming Carboxylic Acids and Derivatives. Carboxylic Acids: RCOOH (RCO 2 H)
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1 Chapter 10 Carboxylic Acids and Derivatives Naming Carboxylic Acids and Derivatives Carboxylic Acids: RCH (RC 2 H) The functional group of a carboxylic acid is a carboxyl group (carbonyl & hydroxyl group) The general formula of an aliphatic carboxylic acid is RC 2 H : : C : H : CH C 2 H Simple open-chain carboxylic acids are names by replacing the terminal e of the alkane name with oic acid The CH carbon is always number C-1 If the compound contains a carbon-carbon double bond, change the infix -an- to -en- CH 2 =CHCH Propenoic acid 1
2 Compounds that have a CH group bonded to a ring are named by using the suffix carboxylic acid The carboxyl group takes precedence over most other functional groups H CH 3 CHCH 2 CH 2 CH 2 C 2 H 5-Hydroxyhexanoic acid CH 3 CCH 2 CH 2 CH 2 C 2 H 5-xohexanoic acid Acid Halides: RCX The functional group of an acid halide is an acyl group bonded to a halogen to name, change the suffix -ic acid to -yl halide the carboxylic acid to -carbonyl Ethanoyl chloroide 2
3 Acid Anhydrides: RCCR (acid + acid) The functional group of an acid anhydride is two acyl groups bonded to an oxygen atom the anhydride may be symmetrical (two identical acyl groups) or mixed (two different acyl groups) to name, replace acid of the parent acid by anhydride CH 3 CC Acetic benzoic anhydride Amides: RCNH 2 (acid + amine) The functional group of an amide is an acyl group bonded to a nitrogen atom to name, drop -oic acid from the name of the parent acid and add -amide if the amide nitrogen is bonded to an alkyl or aryl group, name the group and show its location on nitrogen by N- the carboxylic acid to -carboxamide if the amide nitrogen is bonded to an alkyl or aryl group, name the group and show its location on nitrogen by N- Esters: RCR (acid + alcohol) The functional group of an ester is an acyl group bonded to -R or -Ar name the alkyl or aryl group bonded to oxygen; follow by the name of the acid but with the suffix -ic acid changed to -ate Cyclic esters are called lactones Cyclic amides are called lactams name the parent carboxylic acid, drop the suffix - ic acid, and add -lactam 3
4 Nitriles: R-C N Compounds containing the -C N functional group are called nitriles The nitrile carbon is numbered C-1 ccurrence and Properties of Carboxylic Acids and Derivatives In the liquid and solid states, carboxylic acids are associated by hydrogen bonding into dimeric structures Carboxylic acids are polar compounds and form very strong intermolecular hydrogen bonds through both their C= and H groups This strong hydrogen bonding has a noticeable effect on boiling points they are more soluble in water than alcohols, ethers, aldehydes, and ketones of comparable molecular weight Water solubility decreases as the relative size of the hydrophobic portion of the molecule increases Hydrophobic region (Water-hating) Hydrophilic region (Water-loving) Decanoic acid (0.2 g/100 ml H2) 4
5 Acidity of Carboxylic Acids Acidity Carboxylic acids are weak acids values of pk a for most aliphatic and aromatic carboxylic acids fall within the range 4 5 The greater acidity of carboxylic acids relative to alcohols is due to two factors: 1.the significant resonance stabilization of a carboxylate anion compared with an alkoxide anion 2.the electron-withdrawing inductive effect of the adjacent carbonyl group on the -H bond 5
6 Electron-withdrawing substituents near the carboxyl group increase acidity through their inductive effect H I Br Cl F CH 2 C 2 H CH 2 C 2 H CH 2 C 2 H CH 2 C 2 H CH 2 C 2 H Increasing acid strength Multiple substitution of electron-withdrawing groups further increases acidity The inductive effect of an electron-withdrawing substituent falls off rapidly with its distance from the carboxyl group Synthesis of Carboxylic Acids xidation of alkylbenzene (chapter 5) Cl Cl Cl CH 3 CH 2 CH 2 C 2 H CH 2 CH 2 CH 2 C 2 H CH 2 CH 2 CH 2 C 2 H CH 2 CH 2 CH 2 C 2 H Increasing acid strength xidation of primary alcohols and aldehydes 6
7 Prepared from nitriles, R-C N RBr RC N RCH Nucleophilic Acyl Substitution Reactions Carboxylic acid derivatives have an acyl carbon bonded to a group that can leave as a stable anion The more electron-poor the C= carbon, the more readily the compound reacts with nucleophiles halide ion is the weakest base and the best leaving group; acid halides are the most reactive toward nucleophilic acyl substitution amide ionis the strongest base and the poorest leaving group 7
8 The Tetrahedral Intermediate RC- H H- Cl RC- H H- CR' RC- H H- R' RC- H H- NH 2 FIGURE 10.4 MECHANISM: Mechanism of the Fischer esterification reaction of a carboxylic acid. The reaction is an acid-catalyzed nucleophilic acyl substitution. verview of Reactions FIGURE 10.5 Road map for the reactions of functional groups in this chapter. 8
9 Reactions of Carboxylic Acids 1. Conversion of Acids into Alcohols by Reduction (RCH RCH 2 H) Lithium aluminum hydride (LiAlH 4 ) reduces a carboxyl group to a 1 alcohol reduction is most commonly carried out in diethyl ether or THF it is not reduced by NaBH 4, a reagent that readily reduces the carbonyl groups of aldehydes and ketones Selective Reduction The carboxyl group is not affected by catalytic hydrogenation under conditions that easily reduce aldehydes and ketones to alcohols. X CH 3 CCH 2 CH 2 CH 2 CH + H 2 5-xohexanoic acid Pt 25, 2 atm H CH 3 CHCH 2 CH 2 CH 2 CH 5-Hydroxyhexanoic acid it is also possible to selectively reduce the carbonyl group of an aldehyde or ketone using the less reactive NaBH 4 2. Conversion of Acids into Acid Chlorides (RCH RCCl) Carboxylic acids are converted into acid chlorides by treatment with thionyl chlorides x CCH 2 CH 2 CH 2 CH 5-xo-5-phenylpentanoic acid 1. NaBH 4 2. H 2 H CHCH 2 CH 2 CH 2 CH 5-Hydroxy-5-phenylpentanoic acid 9
10 3. Conversion of Acids into Esters (RCH RCR ) Fischer esterification reaction Esters can be prepared by treatment of a carboxylic acid with an alcohol in the presence of an acid catalyst, most commonly H 2 S 4 or gaseous HCl Reversible reactions (depend on solvent) 4. Conversion of Acids into Amides (RCH RCNH 2 ) Amide are difficult to prepare directly from acids At high temperature Chemistry of Acid Halides Acid chlorides are prepared from carboxylic acids by reaction with thionyl chloride 10
11 Acid chlorides are among the most reactive of the various carboxylic acid derivatives and can be converted into many other kinds of substances 1. Conversion of Acids Chlorides into Acids (RCCl RCH) Acid chlorides react with water to yield carboxylic acids the substitution of Cl by H Cl 2. Conversion of Acids Chlorides into Esters (RCCl RCR ) Acid chlorides react with alcohol to yield esters The reaction usually carried out in the presence of an amine base such as pyridine, which reacts with HCl and prevents it from causing side reaction 3. Conversion of Acids Chlorides into Amides (RCCl RCNH 2 ) Acid chlorides react with ammonia and with amines to give amide ne extra equivalent of ammonia is added to react with the HCl generated 11
12 Chemistry of Acid Anhydrides The reactions of acid anhydrides is similar to that of acid chloride The best method for preparing acid anhydrides is by a nucleophilic acyl substitution reaction of an acid chloride with a carboxylic acid anion (Tylenol) Acid anhydrides are inefficient to use, and acid chlorides are normally used instead Acid anhydrides are inefficient to use, and acid chlorides are normally used instead (Tylenol) 12
13 Chemistry of Esters Ester are usually prepare from acids or acid chlorides Many simple esters are pleasant-smelling liquids that are responsible for the fragrant odors of fruits and flower Fat 1. Conversion of Esters into Acids (RCR RCH) Ester are hydrolyzed either by aqueous base or by aqueous acid to yield a carboxylic acid plus an alcohol Hydrolysis in aqueous acid is the reverse of Fischer esterification (H 2, H 2 S 4 ) 13
14 Hydrolysis in basic solution is called saponification Two differences between hydrolysis of ester in aqueous acid and aqueous base: 1. In aqueous acid: acid is required in only catalytic amounts. Reversible in aqueous acid. H 2 RCCH 3 + NaH RC - Na + + CH 3 H 2. In aqueous base: not just a catalyst, it is a reactant. Irreversible in aqueous base. 2. Conversion of Esters into Acohols by Reduction (RCR RCH 2 H) Esters are reduced by treatment with LiAlH 4 to yield primary alcohols Hydride ion (:H - ) adds to the carbonyl group followed by elimination of an alkoxide ion to yield an aldehyde Further reduction of the aldehyde gives the primary alcohol 14
15 3. Conversion of Esters into Acohols by Reaction with Grignard Reagents (RCR RCH 2 H) Grignard reagent react with esters to yield a tertiary alcohol in which two of the substituents on the hydroxylbearing carbon are identical Chemistry of Amides Amides are usually prepared by reaction of an acid chlorides with an amine 15
16 1. Conversion of Amides into Acids (RCNH 2 RCH) Amides are much less reactive than acid chlorides, acid anhydrides, and esters Amides undergo hydrolysis to yield carboxylic acids plus amine on heating in either aqueous acid or base 2. Conversion of Amides into Amines by Reduction (RCNH 2 RCH 2 NH 2 ) Amides are reduced by LiAlH 4 The product of this reaction is an amine rather than an alcohol This reaction does not occur with other carboxylic acid derivatives Chemistry of Nitriles Nitriles are not acid derivatives, but the chemistries of nitriles are so similar to carboxylic acids Both functional groups have a carbon atom with three bonds to an electronegative atom, and both contain a multiple bond The preparation of Nitriles is by the S N 2 reaction of cyanide ion with a primary alkyl halide Reaction of Nitriles 16
17 Like carbonyl groups, nitriles are strongly polarized The nitrile carbon atom is electrophilic and undergoes attack by nucleophiles 1. Conversion of Nitriles into Carboxylic Acids (RCN RCH) Nitriles are hydrolyzed in either acidic or basic solution to yield carboxylic acids and ammonia (or an amine) 2. Conversion of Nitriles into Amines by Reduction (RCN RCH 2 NH 2 ) Reduction of nitriles with LiAlH 4 gives a primary amines, just as reduction of an ester gives a primary alcohol 3. Conversion of Nitriles into Ketones by Reaction with Grignard Reagents Grignard reagent add to nitriles to give intermediate imine anions that can be hydrolyzed to yield ketones 17
18 Polymers from Carbonyl Compounds: Polyamides and Polyesters There are two main classes of synthetic polymers: Chain-growth polymers (chapter 4) Step-growth polymers Step-growth polymers are prepared by polymerization reactions between two difunctional molecules, with each new bond formed in a discrete step, independent of all other bonds in the polymer Nylons The best-known step-growth polymers are the polyamides, or nylons Nylons are usually prepared by reaction between a diacid and a diamine Polyesters polyesters are usually prepared by reaction between a diacid and a dialcohol (at 280 o C) 18
19 Enzymes in rganic Synthesis 19
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