CHEM 322 Reagents (Professor Hietbrink)

H2, lindlars

alkyne to cis alkene

Li, NH3

alkyne to trans alkene

H2, Pd

removes pi bond for alkynes and alkenes (same amount of carbons)

AlCl3, RCl

Adds RCl, without the Cl

Br2, FeBr3

Adds Br to benzene ring

ortho, para

Cl2, FeCl3

adds Cl

ortho, para

Br2, light

adds Br

Sulfur group, pyrdiine

adds sulfur group to OH

H2SO4, HNO3

adds NO2

H2SO4, SO3

adds SO3H

bullet nucleophile

replaces molecule

HBR, HOOH, light

repalces double bond with Br

LDA

repalces strong acid (BR or Cl) with a double bond

Br2 alone or HBr + II

repalces double bond with 2 Br's

mcPBA

replaces double bond with an epoxide

Heat ring closure

same side

light ring closure

different sides

a) LiAlH4, b) H+

carbonyl to OH

PCC

OH to carbonyl

HgSO4, H2SO4, H2O

terminal alkyne to ketone

triple bond to carbonyl

a) epoxide, b) H+

ROH chain repalces molecle

H2O, heat

OH repalces molecule

Conc H2SO4, heat

double bond repalces OH

OH to double bond

A) BH3, b) HOO-

OH repalces double bond

double bond to OH

Conc H2SO4, SO3

adds SO3H

Dilute H2SO4

removes SO3H

H2, Pt

NO2 to NH2

Zn, HCl

NO2 to NH2

a) KMnO4, KOH, heat, b) H+

carbon chain to carboxylic acid

HNO2, HCl

NH2 to N triple bond N

N triple bond N to OH

H+, H2O

Alkene to alcohol

H+, H2O

Zn/Hg, hcl, h2o

reduces ketone

gets rid of carbonyl

a) HB(Sia)2, b) HOO-

triple bond to carbonyl/aldehyde

a) O3, b) DMS

double bond to carbonyl

primary alc + PCC

aldehyde

seondary alc + PCC

ketone

primary alc + H2CrO4

carboxylic acid

secondary alc + H2CrO4

ketone

aldehyde + H2CrO4

carboxylic acid

know acetals

acetal = O

thioacetal = S

a) RLi, b) H+ + ketone

tertiary alc

a) LiAlH4, b) H+ + ketone

secondary alc

a) RMgBr b) H+ + aldehyde

secondary alc

a) NaBH4, b) H+ + aldehyde

primary alc

a) EtMgBr, b) H+

Ring with carbonyl, carbonyl turns to OH

a) Et2CuLi, b) H+

adds carbon group to a ring with a carbonyl

PPH3

carbonyl to double bond

H2NNH2, KOH, heat

carbonyl to alkene

RCO3H

adds O

there will be three O's in the final product

Primary alcohol or aldehyde + H2CrO4

carboxylic acid synthesis

a) KMnO4, KOH, H2O

carboxylic acid to a benzene ring

Grignard + a) CO2, b) H+

grignard replaced with carboxylic acid

SOCl2

OH in CA replaced with Cl

P2O5

anhydride formation

RHS, H+

thiester formation

RO, H+

ester formation

RNH, DCC

amide formation

decarboylation, get rid of carboxylix acid

heat

Acid cl and anhydride to carboxylix acid

H2O

thioester and ester to carboxylic acid

H+ or OH-

amide to carboxylic acid

H+ or OH- heat

acid cl can become wbat derivatives

anhydride, thiester, ester, amide

anhydride can be come what derivaties

thioester, ester, amide

thioester can become what derivtaive

ester, amide

ester can become what derivatives

amide

amide can become wha derivative

no conversion

what derivatives can use a)LiAlH4, b)H+ and what do they become

they become alcohols

Acid Cl

Anhydride

Thioesetr

Ester

No amide

TMSCl or TIPSCl

add TMS or TIPS to one of the OH's

TBAF

brings back the OH molecule that has TMS or TIPS connected to it