CHEM 239 Solvents

(CH3)2CuLi

“Gilmans’ Reagent” is a organometallic nucleophile used to craft some new C-C bonds by essentially replacing a halogen like Br with a methyl group.

Can also be used to add a methyl group via 1,4 addition on to a conjugated system in which one of those conjugations is from a carbonyl group. Use in combination with H2O if you want this (the H2O acts as an acid workup in which the compound will be saturated).

1) LiAlH4, 2) H3O+

This guy is a reducing agent with a vendetta against carbonyls. Turning those johns into alcohols is his favorite past time. Even with there’s an alkene sitting right next to that carbonyl. (Only reduces carbonyls, not alkenes)

HBr

This guy will add a Br to an alkene, use it with peroxides to get it to do anti-markovnikov addition.

PBr3

This MF will up and swiss cheese an OH and replace it with a Br. Can be useful when trying to craft some organometallics.

Li, ether

Used for making organolithium, which is a super reactive nucleophile. Good for selectively reacting with carbonyls as opposed to alkenes. Makes new C-C bonds.

Br2, OH

We will use this to somehow make an alpha carbon a good leaving group (turn a ketone into a carboxylic acid for example).

Br2, H3O+

Can be used to add one Br to an alpha carbon. Stops at one.

NaOH, H2O, heat

Aldol addition and condensation solvent/base shits.

1) NaOR,  2) Electrophile, 3) H3O+

Michael’s solvent/base shits.

H2, Pt

Primary catalytic hydrogenation for fusing N— type compounds in place of C=O.

K2CrO7, H2SO4

Primary oxidizing agent for turning things into carboxylic acid for example.

PCC

Gentle oxidizing agent. Only turns OH to carbonyl O. Only oral type shit, not all the way.

SOCl2

Turns OH to Cl. Great for when you wanna replace that OH with something else.

pyridine

Just a lil solvent for making the NH groups comfortable with being nucleophilic. They just need a lil push.

1) NaOH, 2) H3O+, 3) heat

Decarboxylation solve

NH3, trace acid (in context of aldehyde)

Add this to an aldehyde to off the carbonyl and replace that joint with an NH. This will produce some H2O as well (2 H’s from teh NH3 and O from aldehyde). You could use this when trying to craft a lil amino acid type shit.

NaCN, trace acid (in context with imine)

Nucleophilic attack on the imine double bond and will make a new C-C bond holy moly.

HCl, H2O (in context of nitril (C=—N))

Will off the N and replace that shit with a whole ass carboxylic acid??? Wha????

Ac2O (in context of amino acid)

This will react with the amine on the amino acid (not the carboxylic acid). This is because the amine is a better nucleophile than the carboxylic acid and this reactant (Ac2O) acts as an electrophile, not a nucleophile. This is useful for protecting the amine from side reactions.

EtOH (excess), HCl (in context of amino acid)

This, like any other etser forming compound will act as a nucleophile and attack the carboxylic acid. It’ll protect the carboxylic acid from side reactions.

Amine protecc

Fmoc (removed via piperidine), Boc (removed via TFA)

Carboxylate protecc

Obzl, H2SO4

Ph3P

Used to make an ylid. Will make in the spot marked by a halogen.

nBuLi

Used to catalyze the attachment of an ylid to another compound. Remember that this will result in a double bond in place of a carbonyl O.