Exam 2 Flashcards
Reactivity of carboxylic acid family least to greatest
carboxylic acid, amide, ester, anhydride, acid chloride
Stability of carboxylic acid family from least to greatest
acid chloride, anhydride, ester, amide, carboxylic acid
Basicity of amines
- less resonance = more basic
- Presence of an EWG = less basic
- More basic = more nucleophilic
- More p character = better base
Aldehydes are more reactive than ketones because of
sterics and hyperconjugation
Primary alcohol + PCC
Aldehyde
Secondary alcohol + PCC/H2CrO4
Ketone
Alkene + O3 and Me2S
2 ketones (ozonolysis)
Carbonyl + strong nucleophile
addition of nucleophile first
Carbonyl + weak nucleophile
protonation first
LiAlH4 is more reactive than NaBH4 because
Aluminum is less electronegative than Boron, so the Al-H bond is easier to break
Ketone + LiAlH4/NaBH4 and H3O+
Secondary alcohol
Aldehyde + LiAlH4/NaBH4 and H3O+
Primary alcohol
R-Br + Mg
R-MgBr (Grignard)
Ketone/Aldehyde + ylide (R’-(-)CH-(+)PPh3)
Replace O with H-C-R’
Alkyl halide + PPh3 + strong base
ylide formation