chp 19-20 runs Flashcards
oxidation of primary alcohol to carboxylic acid
reagent : Jones
reagent : PCC and H20
oxidation an aldehyde
reagent Jones
product Carboxylic Acid
Carbonation of R-X
reagent : 1)Mg (or Li) and batman
2) Co2
3) H3O+
Product: 1)RMg-X
2) RCOO-
3) RCOOH
Nitrile Hydrolysis of R-X
reagent 1)NaCN
2)H+ , H20, Heat
product 1)R-CN
2) RCOOH
note: if there is no heat product is only RCONH2
bc heat is needed to kick out NH2 bc NH2 donates electrons for resonance
Acyl halide (cl) synthesis from carboxylic acid
reagent : SoCl2
Product : RCOCL
note: an SN2 rxn
Acyl Halide synthesis from carboxylic acid
Reagent : PX3 (X=Br or CL)
Product: RCOX
Anyhdride synthesis
Reagent : Carboxylic Acid + Acyl Halide
Product: Anhydride
alcohol of carboxylic acid attacks the carbon of acyl halide. The LG is the halogen
can you make an anhydride with two carboxylic acids?
yes but the yield is better if it is with one acyl halide bc halogens are better LG
ester (RCOOR’) synthesis from carboxylic acid
Reagent: R’OH, H+, Heat
Product ROR’
to close up a chain to make an Ester with OH on both ends of the chain you need?
Heat
Ester (RCOOR’) synthesis via substitution from carboxylic acid
Reagent : 1)NaOH
2)R’-X
Product: 1) RCOO-
2) RCOOR’
Amide Synthesis(RCONH2) from carboxylic acid
Reagent : NH3, heat
Product RCONH2
note: reagent can be NRH2 or NR2H, the product will always be one H less than reagent
Acyl Halide Hydrolysis
Reagent: 1)H20
Product: RCOOH
alcoholysis of acyl halide
Reagent : 1) R’OH, Pyridine (to stop formation of HX)
Product: RCOOR’
Ammonolysis of acyl halide
Reagent : NH3, or NH2, or NH
Product : RCOONH2, Or..
Alkylation of Acyl Halides
Reagent: R’Li or R’MgX and Ether
Product : RCOOR’ or RCOHRR (if there is 2 equivalent of product)
Reduction of acyl halide (2 ways)
Reagent: NaBH4, ETOH
or
1)LiAlH4, ether,
2) H3O+
Product : Primary alcohol (two hydrogens attached and C=O turns into C-OH)
Reagent : 1)LiAl[OC(CH3)3]3, THF
2) H3O+
Product: RCOH (aldehyde)
note: Dibal is too strong and will not stop at aldehyde
Reduction of carboxylic acids
Reagent : 1)LiAlH4, Ether
2)H3O+
Product : Primary alcohol
note: NaBH4 is too weak and won’t reduce
Dibal does not react with carboxylic acids
Zelinsky RXN
reagent: Br2 and P(trace)
Product: bromination of alpha carbon
note: alpha carbon needs at least one hydrogen or else its no RXN
anhydride Hydrolysis
reagent: H20
Product : two carboxylic acids
alcoholysis of anhydrides
reagent : R’OH
product : carboxylic acid + RCOOR’
Ammonolysis of anhydrides
reagent : NH3
Product: RCONH2 + RCOOH
note: if there is an excess of NH3, RCOOH will be deprotonated
alkylation of anhydrides
Reagent: R’Mgx or R’Li
product : RCOHR’R’ + RCOOH
reduction of anhydride
reagent : NaBH4, EtOH
or 1)LiAlH4, ether
2)H3O+
Product : 2 primary alcohol
