Organic Chemistry Questions

making mono, di, and tri substituted alkenes. Tetrasubstituted products are difficult to prepare due to steric hindrance in the TS

desulfurization, therefore we have an alternative to the Wolff-Kishner/Clemmenson reductions

unstabilized (no resonance) reactants produces cis (Z) product favored (kinetic), stabilized forms trans, E product favored (thermodynamic)

amine attacks carbonyl group, oxygen protonated to remove negative charge, deprotonation gives a carbinolamine (H taken from the N), OH group protonated into a good leaving group, water leaves, C=N double bond forms, intermediate deprotonated to generate enamine

imine formation (Hydrazone), which can be reduced under strongly basic conditions (KOH/H2O)

Hydrazine (N2H4) attacks a carbonyl via the imine formation mechanism shown earlier, forming a hydrazone which is structurally similar to an imine

HCN is highly toxic, so KCN/HCl is typically employed. Nitriles are precursors to amines/carboxylic acids

converts a carbonyl group into a new C=C double bond where no bond existed before

must be acid catalyzed (protonation of the carbonyl group activates it such that it will react with the weak nucleophile, ROH)

one of the protons is removed (resonance-stabilized intermediate), intermediate protonated, another proton removed, nitrogen gas expelled (carbanion), carbanion protonated

nucleophilic attack on carbonyl carbon, proton transfer, asymmetric ketone gives chirality center (enantiomers)

strong nucleophile attacks, then oxygen gets protonated, or oxygen gets protonated and then weak nucleophile attacks

so that the less hindered end of the double bond comes from the ylide

carbonyl carbon has a partial positive charge and will react as an electrophile; the oxygen atom has a partial negative charge and is nucleophilic

acetals are hydrolyzed by addition of dilute acid. Excess water favors the formation of the ketone/aldehyde

aldehyde carbon is number 1 (so no locant), if the aldehyde group attached to a ring, the suffix carbaldehyde is used

Betaine formation, oxaphosphetane formation, oxaphosphetane collapses, forming carbonyl (ketone or aldehyde) and PPh3O

the hydroxide ion (strong nucleophile) attacks the carbonyl group (electrophile). Protonation of the intermediate gives the hydrate

for water (weak nucleophile) to attack, the carbonyl group must first be activated by protonation, deprotonation then gives the hydrate

adding a nucleophile and H to the C=O, electrophilic C is sp2 and planar, so is attacked from top/bottom giving an sp3 carbon