Carboxylic Acid And Derivative Rxns Flashcards
Carboxylic acid-> (SOCL2 and pyr)
Acid chloride
- acid mech
- also works with alcohol but undergoes inversion if chiral
Carboxylic acid -> (base and X-R)
Ester (replace H from acid with R)
- basic mech
Carboxylic acid -> (R-OH (xs) and acid)
Ester (replace OH with OR)
- acidic mech
1’ Amide -> (SOCl2 and pyr)
Nitrile
- resonance then acidic mech
Acid chloride or anhydride -> (NaBH4 (2 equiv) and ROH)
1’ alcohol
- basic mech
Ester -> (1. LAH (2 equiv) 2. Quench)
1’ alcohol
- no mech
Amide -> (1. LAH (2 equiv) 2. Quench)
Amine
- replace double O with 2H
Nitrile -> (1. LAH (2 equiv) 2. Quench)
1’ amine
- get rid of triple bond, replace N with NH2
Acid chloride, anhydride, or ester -> (1. grignard 2. Quench)
3’ alcohol
- gets rid of LG, changes O to OH, and adds 2 grignard c chains
Acid chloride or anhydride -> (R2CuLi)
Ketone
- replace LG with R
Carbonyl with LG or Nitrile -> (acid and H2O)
Carboxylic acid
- replace LG or N with OH
Alpha H connected to C=O -> (irreversible base and R-X)
Replaces H with R
- LDA = less sub
- NaH = more sub
Ketone or ald -> (1. Acid, HNR2, -H2O 2. Conjugated C=O 3. Acid, H2O)
Replaces alpha hydrogen with conjugated C=O
- remove conjugation and place in alpha H space
Ketone or ald -> (acid, X2, H2O)
Alpha halogenated
- replaced 1H with X (Br, I, Cl)
Carboxylic acid -> (PBr3, Br2, H2O (xs))
Replaced alpha H with Br
Ketone -> (-OH (xs), X2 (xs), H2O)
Replaces all alpha H with X
Aldehyde or ketone -> (ald or ket, -OH, H2O)
Replaces alpha H with second ald or ket (second ald or ket’s double O replaced with OH)
aldehyde or ketone -> (ald or ket, -OH, and heat)
Alpha, beta- unsaturated carbonyl
- adds second ald or ket to alpha H space and replaces double O with a pi bond
Ester -> (Ester, -OR and quench)
Beta-keto Ester
- Rids second Ester of its OR and places it in the first Esters alpha H space
Nitro -> (1.Fe or Zn, HCl, 2. NaOH)
1’ Amine
- keeps R but replaces NO2 with NH2
Amide -> (1. LAH (xs), 2. Quench)
Amine
Nitrile -> (1. LAH (xs), 2. Quench)
1’ Amine
R-X -> (1. -N3, 2. Reducer (H2/cat or 1. LAH, 2. Quench))
1’ Amine
- “R-NH2”
- replaces X with NH2
Phthalimide -> (1. Base, 2. R-X, 3. H2NNH2 or acid, H2O, heat)
1’ Amine
- “R-NH2”
Aldehyde or Ketone -> (amine, acid, and NaCNBH3)
Amine
- replaced double O with singly bonded amine
Amine -> (1. Me-X, 2. Ag2O, H2O, heat)
Hofmann Alkene
- rids of NH2 and makes a less sub alkene instead
- H2O and heat can be replaced with a strong base and heat
Beta keto ester -> (1. Base, 2. R-X, 3. Acid and H2O)
Ketone
- draw ketone, place R from R-X into R space of ketone
Malonic Ester -> (1. Base, 2. R-X, 3. Acid and H2O)
Carboxylic Acid
- draw Carboxylic acid, place R from R-X where Carboxylic acid R is
2 Thiols -> (oxidant)
Disulfide
- reductant to reverse (Zn, HCl)
Sulfide -> (ox) ? -> (ox) ?
Sulfoxide (S, 2 methyl, 1 O)
Sulfone (S, 2 methyl, 2 O)
- Ox can be NaIO4 or H2O2, etc
R-OH -> (TBSCl or TMSCl and Et3N)
R-O-TBS or R-O-TMS
-replace H with TBS or TMS
R-O-Si -> (1. TBAF 2. Quench)
R-O-H
- replace Si with H
Cl3CH -> (1.-OH 2.alkene)
Turn double bond into epoxide form with 2 Cls
R-SnBu3 -> (R-X, Pd catalyst)
R-R and X-SnBu3
R-B -> (R-X, Pd catalyst, and -OR or -OH)
R-R and HO-B
R-ZnX -> (R-X, Pd catalyst)
R-R and XZnX
Alpha methyl ketone -> (-OH (xs), X2 (xs), H2O, then Quench)
Carboxylic acid
