Organic Chemistry Reactions

polar protic solvent

CH3OH, H2O

polar aprotic solvent

DMSO, DMF, acetone (+electroneg)

SN1

sub mech with 2 products

solvolysis

rxn with solvent is also nucleophile

rearrangement

formation of a more stable carbocation

3, 2, 1, methyl

the carbon position that favors SN2 rxns (worst to best)

methyl, 1, 2, 3

the carbon position that favors SN1 rxns (worst to best)

strong

best nucleophile for SN2

weak

best nucleophile for SN1

25

best temperature for subsititution rxns

55

best temperature for elimination rxns

E2 zatiseu product

SSB reaction

E2 hofman product

SBB reaction

methyl, 1, 2, 3

best carbon placement for elimination rxns (worst to best)

-Cl, -Br, -I, -SH, -CN

strong nucleophile/weak base (better for subbed rxns; best for SN2)

t-ButO-, DBU, DBN, NaH

weak nucleophile/strong base (better for elimination; best for E2)

-OH, -OCH3, -OCH2CH3

strong nucleophile/strong base (better for both; best for SN2/E2)

H2O, CH3OH, CH3CH2OH

weak nucleophile/weak base (better for both; best for SN1/E1)

polar aprotic

best solvent for SN2 or E2 rxns

polar protic

best solvent for SN1 or E1 rxns

SN1 of OH

subsititution rxn with one product under specific conditions

SN2 of OH

substitution rxn with 2 products

methyl, 1

carbon placement for OH/ether SN2 rxn

2, 3

carbon placement for OH/ether SN1 rxn (check chirality)

dehydration

E1 reaction of an OH

sulfonate ester

SN2 better OH with larger structures

williamson ether synth

SN2 reaction to make an ether with a preference in reagents

formation of a ring

intermolecular rxn closing

ether breakdown

SN2 ether reaction

less subbed side bond

epoxide under SN2 in basic conditions

more subbed side bond

epoxide under SN1 in acidic conditions (WN/A)

what is added?

addition rxn questions 1

where are they added?

addition rxn questions 2

why?

addition rxn questions 3

HBR

Markovinkov addition of a halogen (alkene)

unsubbed, monosub, disub, trisub, tetrasub

The order of alkene substitution from worst to best stability

hofman

structure with less subbed alkene

zaitseu

structure with more subbed alkene

H2O, H2SO4/H3O+

acid-cataylzed hydration

1) Hg(OAc)2, H2O, THF 2) NaBH4

oxymercuration demurcuartion

1) BH3, THF 2) H2O2, NaOH

hydroboration-oxidation

H2, Pt, Pd, N

catalytic hydrogenation

Br2, CCl4

halogenation

Br2, H2O

halohydrin formation

OsO4, t-ButOUH/t-ButOH, NaOH

Oxidation (OH)2 syn

1)mCPBA, CH2Cl2 2) H3O+

Oxidation (OH)2 anti

1)O3 2)Zn, H2O/CH3SCH3

atomic scissors

HBr excess terminal

hydrohalogenation

HBr excess internal

Hydrohalogenation

Br2, CCl4 excess

halogenation

lindar’s catalyst

alkyne hydrohalogenation reagent for cis alkene

Na, NH3(l)

alkyne hydrohalogenation reagent for trans alkene

number of carbons?

synthesis starting questions 1

functional groups?

synthesis starting questions 2

location of function groups?

synthesis starting questions 3

conjugated diene

extended overlap of p orbitals between double and single bonded carbons

1,2 product

kinetic product with 0C temp requirements, easier to form but less stable

1,4 product

thermodynamic product with 40C temp requirement, harder to form but more stable

initiation

radical halogenation step 1

propagation of radical

radical halogenation step 2

propagation of C radical

radical halogenation step 3

termination

radical halogenation step 4

NBS

promotes radical formation instead of Br2 Addition

Na, NH3

alkyne reduction

HBr, H2O2

anti-Markovnikov bromination