chem 215 exam 1

PCC reagents

CrO3/pyridine/HCl

Swern reagents

1) DMSO/oxalyl chloride 2) triethalmine

reactive species in Swern

chloro dimethyl sulfonium (Ch3)2-S+-

Cl

Jones reagents

CrO3/H2SO4/H2O

aldehyde

carboxylic acid

ketone

carbonyl

alkoxide

base just deprontonates

1° alcohol w/ CrO3/pyridine/HCl

PCC, aldehyde

2° alcohol w/ CrO3/pyridine/HCl

PCC, ketone

1° alcohol w/ 1) DMSO/oxalyl chloride 2) triethalmine

Swern/ aldehyde

2° alcohol w/ 1) DMSO/oxalyl chloride 2) triethalmine

Swern, ketone

1° alcohol w/ CrO3/H2SO4/H2O

Jones, carboxylic acid

2° alcohol w/ CrO3/H2SO4/H2O

Jones, ketone

2° alcohol w/ ANYTHING

ketone

1° alcohol will make?

aldehyde with PCC or Swern, carboxylic acid with Jones

hemiacetal

acetal

hemiketal

ketal

N group attaching on a carbonyl will form an _______

amine

epoxide ring opening in basic conditions

attack the least substituted carbon

epoxide ring opening in acid conditions

first protonate O, then attack most substituted carbon

H- additions to carbonyls: reagents

Li+ AlH4-, Na+ BH4-

CN- (cyanide) addition to carbonyl

:C-≡N: Na+

:CH3- addition to carbonyl

CH3 MgBr

imine formation

N replaces the O in the carbonyl, use catalytic amount of weak acid, N is the starting nucleophile

-one suffix

=O

-thiol suffix

-S-H

carboxy- prefix

COOH-

methane

CH4

ethane

CH3-CH3

under basic conditions...

DEPROTONATE your NUCLEOPHILE

under acidic conditions...

PROTONATE your ELECTROPHILE

oxidation number

just look at the first things the atom is attached to, the same atom attached counts as 0, more electronegative atom takes the negative charge towards it

/\/ OH w/reagent HCl or HBr or 1)TsCl, pyridine 2) NaCl

makes /\/ X (X is Cl or Br)

/\/ OH w/reagent Cl-Cl-S=O, pyridine

makes /\/ X (X is Cl)

/\/ OH w/reagent PBr3 or PCl3

makes /\/ X (X is Br or Cl)

needed trajectory/stereochem for alkoxides to form epoxides

in chair formations of rings you want the O- and the leaving group to be either BOTH equatorial or BOTH axial: if one away on a ring stereochem should be opposite (1 wedge and 1 dash), if two away on a ring stereochem should be same (2 wedges or 2 dashes); if two away on a ring and stereochem is opposite you do E2 and form a double bond