Orgo Reactants

LDA

Performs E2 reactions

• N takes the H - makes N neutral charged

• Electrons attached to H go to the C-C bond

• LG takes its electrons

>-:N:^--< Li⁺

Conc HCl & heat

Performs SN1 reactions

• Can react multiple times

• Can have carbocation rearrangement

HCl

Performs addition

• Epoxide opening

• O takes the H

• Break bond to make the most stable carbon

• Can also do normal addition

conc H₂SO₄ & heat

Performs E1 reactions with OH

• Both E and Z products

• H attaches to OH, making H2O

• H2O leaves, causing + charge

• O on the nuc takes an H, and its electrons form a double bond, getting rid of the + charge

• Basically, OH becomes a double bond between the carbon with OH and the most stable carbon

NaH

Forms epoxides

• H reaches out and takes the H attached to an OH group

• Basically, electrophile with OH and a good LG reacts with this to form an epoxide

a) NaH

b) R-LG

Adds a carbon chain to an O

• When electrophile has an OH

• R = carbon chain

Excess NaNH₂, heat

Elimination reaction

• Forms a triple bond

• Will react until it can’t

• Nuc reaches out and takes an H

• LG leaves

• Move electrons accordingly

a) NaNH₂

b) R-LG

Adds a carbon chain to terminal alkyne

Br₂

Adds nuc to both carbons in a double bond (on opposite stereochem)

• Double bond reaches out and takes one part, leaving a + charge

• The other part attaches to where the + charge is; OPPOSITE stereochem

• (±)

Br₂, H₂O

Adds nuc to least substituted carbon and OH to most substituted carbon (on opposite stereochem)

a) Hg(OAc)₂, H₂O

b) NaBH₄

Addition reaction

• Follows normal rules

• Adds OH to most substituted carbon

• Does NOT do carbocation rearrangement

a) R-Li

b) H⁺

Can do SN2 and E2 reactions

• Adds carbon chain to molecule

• Epoxide opening

• Electrons attaching Mg to C take C chain and attach to one part of epoxide

• O takes its electrons and epoxide opens, leaving O with a - charge

• O takes H⁺ to make OH

• Can also do non-epoxide reactions which would be (±)

LiAlH₄

Turns a group into another group

• Aldehyde → alcohol (primary)

• Ketone → alcohol (secondary)

• Carboxylic acid → alcohol (primary)

• Esters → alcohol (primary)

• Amides → amines

• Nitrile → amines (primary)

• Epoxides → alcohols

• Alkyl halides → alkanes

Basically turns Os into alcohols

a) NaBH₄

b) H⁺

Turns aldehydes and ketones into alcohols

mCPBA

Makes alkenes into epoxides

• Turns double bond into epoxide

a) BH₃

b) HOO^-

Adds OH to alkenes

• Addition

• Puts OH on LEAST substituted carbon

• (±)

a) O₃

b) DMS

Cuts at the double bond and puts oxygen at the end (both ends)

• Can “cut” hexanes

a) OsO₄

b) NaOH, H₂O

Adds 2 OH groups to alkene; same stereochem (±)

CH₂N₂

Turns alkene into a 3 carbon triangle

• Like an epoxide but no “O”, just carbons

• (±)

H⁺, H₂O, heat

Turns alkyne into ketone

• Or HgSO₄, H₂SO₄, H₂O

a) Hb(Sin)₂

b) HOO^-

Turns alkyne into aldehyde

Br₂ + light

Radical reaction

• Adds ___ to the molecule on the MOST substituted carbon

• H leaves; one of its electrons goes in on itself, creating a radical

Cl₂ + light

Adds ___ to molecule, does not have regiospecificity so it will cause a mixture

HBr + ROOR + light

Adds ___ to LEAST substituted carbon of a double bond

H₂, Pd

Turns alkynes and alkenes into alkanes

• Gets rid of double and triple bonds

H₂, Lindlars

Turns alkynes into Z alkenes

• Does not react with alkenes

Li, NH₃ (I)

Turns alkynes into E alkenes

• Does not react with alkenes

Mg and Li

Makes Grignard with carbon chains that have leaving groups Br, Cl, or I

• Mg sticks itself between a halogen and the C attached to it

• Li replaces halogen

KCN (or HCN, NaCN, etc), H₂O (or HCl, HBr, etc)

CN^- is a bullet nucleophile

• Only does SN1

• Called “cyanohydrin formation”

• Whatever is in front of CN^- is positively charged and not part of the reaction