orgo 2 topic 4

nucleophiles that are non-equilibrium

H and C as nucleophiles but do not act as leaving groups, ex: hydrogen nucleophiles (LiAlH4, NaBH4), carbon nucleophiles (ylids, cyanide, sodium acetylides), another nucleophile (peroxyacid -> ester)

nucleophiles that are in equilibrium processes

O and N as nucleophiles and leaving groups, ex: oxygen nucleophiles (water, alcohols), nitrogen nucleophiles (primary and secondary amines, hydrazines)

ozonolysis of alkenes

1. O3, 2.DMS, makes aldehyde

markovnikov hydration of alkynes

H2SO4, H2O, HgSO4, enol as intermediate then tautomerizes, creates ketone

antimarkovnikov hydration of alkynes

1) R2BH, 2) H2O2, NaOH, enol as int then tautomerizes, creates aldehyde

strong oxidizing agents for primary alcohol (makes it carboxylic acid)

Na2Cr2O7, H2SO4, H2O OR 1) KMnO4, KOH, H2O, 2) H3O+ OR CrO3, H2SO4, H2O

selective oxidizing agents from primary alcohols (makes it aldehyde)

DMP OR PCC OR oxalyl chloride and DMSO

oxidizing agent for secondary alcohols

can use any bc it can only become ketone (strong or selective ok)

oxidizing agent for tertiary alcohols

none

reduction of ketone/aldehyde to make secondary/primary alcohol

1) LiAlH4, 2)H2O OR 1) NaBH4, 2) H2O

reduction of carboxylic acid or ester

1) LiAlH4, 2) H2O (makes primary alcohol vial aldehyde)

ester, carboxylic acid, or acid chloride to aldehyde

1) LiAlH (t-BuO)3, -78 C, 2) H2O OR 1) DIBAL-H -78 C, 2) H2O

cyanide anion

can be used in SN2 reaction and then use the triple bond for other things

grinard reaction

R-X + Mg

epoxides

just remember they are a thing. hit them with H3O+ and they open up and boom alcohol

wittig reaction

phosphonium ylids as nucleophile, then goes through addition (electrons from C to C next to O and double bond from O to P+), and elemination (creates alkene)

formation of phosphonium ylids

start wiht Ph3P and C as nucleophile, SN2 then acid base reaction to make one big happy molecule

alcohols as nucleophiles

add acid to make electrophile more electrophilic, makes hemiacetal then acetal

formation of acetals (turns C=O into 2 OR groups)

protonation of oxygen, nucleophilic attach (ROH , deprotonation, protonation of alcohol, loss of leaving group (H2O), Nu attack (ROH), deprotonation

hydrolysis of acetals

reverse of formation

protecting the ketone

HOCH2CH2OH, H2SO4

peroxyacids as the nucleophile/the baeyer-villiger oxidation

RCO3H, adds O to make ester

replace c=o with 2 oh groups

h2O

replace c=o with 2 OR groups

ROH

replace c=o with c=NR

RNH2

replace o=c with c=NHNH2

NH2NH2

replace c=NHNH2 with 2 H

KOH, H2O, heat (wolff-kishner, the H acts as an acid with the base, notice the resonance (important))

replace c=o with NOH

NH2OH

replace o=c with c=c-Nr2

R2NH (secondary amines)

replace c=o with OH and CN

NaCN

replace c=o with CCR and OH

RCC-, Na+

replace c=o with C=CR2

R2C-PPh3

replace O=C with R and OH

RMgBr