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Ch.22 CA Derivatives

Nucleophilic Acyl Substitution- Reactivity of Carboxylic Acid Derivatives

Define Acyl Goup Z--COR: includes carboxilic acids, acid chlorides, anhydrides, esters, and amides. Z: OH, Cl, OCOR(anhydride), OR',NR'2
Define Lactones, y-lactone Cyclic esters. An ester in a five-membered ring.
Define Lactams Cyclic amides. An amide in a four-membered ring. An amide in a five-membered ring.
Why can't aldehydes and ketones undergo nucleophilic acyl substitution? Because aldehydes and ketones have no leaving group on the carbonyl carbon and cannot undergo nucleophilic substitutiion.
Why can Nitriles undergo nucleophilic substitution? Nitriles are compounds that contain a cyano (C=-N) group bonded to an alkyl group. Both RCN & ZCOR have one Catom with 3bonds to e-negative atoms. CN sphybridized, 180, 1sigma, 2pi, e-philic carbon.
How do you determine the basicity of the leaving group? You can compare pKa values of the conjugate acids HZ to determine the relative basicity of the LG Z. (WB|SA) Cl-, RCOO-, -OH = -OR', -NR2 (SB|WA|More Stable) The stonger the base, the stable the RCOZ, added resonace stabilization. WB=more reactive.
Naming an Acid Chloride—RCOCl [1] For acyclic acid chlorides: Change the suffi x -ic acid of the parent carboxylic acid to the suffi x -yl chloride [2] When the –COCl group is bonded to a ring: Change the suffi x -carboxylic acid to -carbonylchlorid
Common parent carboxylic acids - Formic acid - Acetic acid - Benzoic acid
Naming an Anhydride [1] Sym'cal anhydrides: change the acid ending of the parent carbox.acid to 'anhydride'. [2] Mixed anhydrides, derived from two diff. carbox. acids: alphabetize the names for both acids and replace 'acid' by the word anhydride
Naming an Ester—RCOOR' [1] Name the R' group bonded to the oxygen atom as an alkyl group -yl. [2] Name the acyl group (RCO-): change the -ic acid ending of the parent carboxylic acid to the suffi x -ate.
Naming an Amide - Primary [1] All 1° amides are named by replacing the -ic acid, -oic acid, or -ylic acid ending with the suffix -amide.
Naming an Amide - Secondary & Tertiary [1] Name the alkyl group(s) bonded to N atom of the amide: Use the prefix “N-” preceding the name of each alkyl group. [2] Name the acyl group (RCO-) with the suffi x -amide:Change the -ic acid/-oic acid of parent carboxylic acid to the suffi x-amide.
Naming a Nitrile [1] Find the longest chain containing CN: + 'nitrile' to parent alkane. [2] Number chain to put CN at C1, omit number. [3] Common names: names of the carboxAs w/same # of Catms: replace -ic acid ending of CA w/ x-onitrile. CN substituent: "cyano"
Physical Properties of carbonyl compounds ALL: LDF, DIP-DIP Primary&Secondary amides: HBONDING
Why do carbonyl acid derivatives undergo nucleophilic acyl substitution rather than addition like aldehyde and ketones? Just like Aldehydes and Ketones, carbonyl acid derivatives react with nucleophiles because they have an unhindered electrophilic carbonyl carbon. However, because they do have a leaving group Z on the carbonyl carbon, they undergo substitution.
Common nucleophiles: -OH, H2O, ROH, RCOO-,NH3,RNH2,R2NH
Steps of predicting/drawing a nucleophilic acyl substitution product: [1] Identify the sp2 hybridized carbon with the leaving group. [2] Identify the nucleophile. [3] Substitute the nucleophile for the leaving group.
Best Leaving Group= Weakest Base(SA) Order derivatives in increacing reactivity. (Worst LG) -NH2, -OH = -OR', RCOO- , Cl -(best LG) To form a substitution product, Z must be a better LG than NU.
What is required in nucleophilic substitution rxn with neutral nucleophiles (H2O, R'OH, NH3, and so forth)? It equires an additional step for proton transfer. [1] Nucleophilic addition at c=o, tetrahedral intermediate. [2] Removal of a proton* [3] Elimination of the leaving group
Anhydrides can't be used to make acid chlorides. Explain why. RCOO– is a stronger base and therefore a poorer leaving group than Cl–. NS occurs only when the LG is a weaker base and therefore a better leaving group than the attacking nucleophile.
Created by: Yourdanos