Reagents Flashcards
Reagents used to oxidize, reduce, break, or create new bonds
ClCH(CH3)2
- Chlorine good leaving group
- Electrophile
- Sp3 Carbon
- Sn1, Sn2, E1, E2
PCl3
- Chlorine good leaving group
- Electrophile
- Sp3 hybridized P
- Nu Attacks -> Sn2
- OH Activation
HCl
- Good Nucleophile
- Strong Base??
- Strong Nucleophilic Acid
- promotes substitution
Tollens
Ag2O, NH4OH, H2O
- no arrow pushing mechanism
- Selectively converts aldehydes to carboxylic acid
- produces a silver mirrror
- radical mechanism
PCC
CrO3, HCl, Pyridine
- Chlorine good leaving group
- Electrophile
- SnAc
- Oxidation: 1 and 2 alcohols
-> SnAc, Acid/Base, E2
Jones
CrO3, H2SO4, H2O
- Cr = O double bond breaks when Nu attacks
- Electrophile
- SnAc, Addition
- Oxidation: 1 and 2 alcohols, aldehydes
-> SnAc, Acid/Base, Addition, E2, Activation
H2SO4
- Strong non-nucleophilic acid
- dehydration w/ R-OH and heat
NaH
- Strong base
- deprotonate OH
LiCH(CH3)2
- Strong base
- great C+ Nu
- makes new C-C bonds
- reacts with C = O or epoxide
- reduction -> SnAc, Addition
LiAlH4
- Strong base
- good H- Nu
- make new C-H bond
- reduction -> SnAc, Addition
Monster - reacts with:
NaBH4
- Weak base
- good H- Nu
- make new C-H bond
- reduction -> SnAc, Addition
Selective - reacts with: Aldehydes, Ketones
ToSyl Chloride
ClTs - Cl-SO2-C ring
- Cl good leaving group
- S=O double bond breaks when Nu attacks
- Electrophile
- SnAc
- OH activation
Thionyl Chloride
Cl2S=O
- Cl good leaving group
- S=O double bond breaks when Nu attacks
- Electrophile
- SnAc
- OH activation
Sulfonate Ester
RO-SO2-CH3
- sulfonate good leaving group
- electrophile (c attached to o)
- Sp3 C
-> Sn1, Sn2, E1, E2
Sulfonyl Chloride
Cl-SO2-CH3
- Cl good leaving group
- S=O double bond breaks when Nu attacks
- Electrophile
- SnAc
- OH Activation
