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49 Cards in this Set

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Eliminating C=C double triple bonds

H² Metal Catalyst

Alkyne to cis alkene

Lindar catalyst

Alkyne to trans alkene

Birch reduction

Keytone to alcohol (+1 substituent)

Gringard Reagent

Synthesize Gringard Reagents

Magnesium + alkyl halide in ether

Ester to tertiary alcohol

2 Gringard/ether then aqueous

Epoxide opening to alcohol

Gringard rxn (least stericly hindered)

Sn2 double bonds/ R group epoxide transfer

Cuprate (R²CuLi)

Reduction of carbonyls/esters

NaBH⁴ or LiAlH⁴ (for esters

Oxidation of alcohols

PCC, Jones, K²Cr²O7 / H² SO⁴ , Dess Martin

Primary Alcohol to Carboxylic Acid

Jones

Alcohol Leaving Group for Sn1 or Sn2

Acidify or PBr³

Carboxylic to Ester

HCl and Primary Alcohol

Cleavage of Diols

IO⁴

Pinacol Rearrangment

Alcohol acidified, 1-2 methyl shift on carbocation, Alcohol deprotenated for collapse in carbonyl

Double bond to epoxide

m-CPBA (peracid)

Epoxide to diol

Acid and water

Splitting C=C bond for two carbonyls

Ozone + MeS

Anti markovnikov addition

Nuclephile radicalized by peroxide

Single bromine addition/ Sn2

NBS and UV

Diers Alder

S-cis conjugated alkene and alkene or alkyne with EWG para favored

SeA

Electophile hits double bond and base hits proton (directing effects)

Chlorination SeA

Cl² + AlCl³

Bromination SeA

Br² FeBr³

Iodination

I² + HNO³

Sulfination

SO³ H²SO⁴

Nitration

HNO³ + H²SO4 (NO²)

Adding Alkyls to Aromatics

Carbocation alkyl and base (AlCl³ Cl/ OH Acid)

Adding acyls to aromatics

Acyl carbocation and base

SnAr

Nu at Halide and adjacent EWG

Adding nuclephile to aromatic

Base and nucleophile

Aromatic additon

H² metal and 1000psi

Directing Effects Aromatic

O,p has line pair for ressonance and activate


M doesn't and deactivate


Halides o,p but deactivate

Reduction to 1,4 cyclohexadienes

Treat with Na in NH3


Substituent as EWG to make parallel


As EDG to make diagnol

Keytone into 3° alcohol

Anionic nucleophile/gringard

Immine creation

Acid catalyzed keytone with 1° amine


(Reversible with water)

Keytal creation

Alcohol or R³SH with acid on keytone


(Reversible with water)

Deoxygenation (removal) of keytone

HS(CH²)³HS + Acid and RaNi


H²NNHTs p-TosH and NaBH³CN

Adding R²N groups to keytones

NR² and acid


Creates a double bond by removing a neighboring proton on near carbon

Hydration of alkyne to aldehyde

(Sia)²BH and H²O²

Formation of any keytone from formaldehyde

Thioacytal creation to nBu-Li reacting with 2 1° halides and reversing with water+acid

Carboxylic acids to keytones

Alkyllithiums

Nitrilea to keytones

Gringard with water and acid

Acylchlorides to aldehydes

LiAlH(O-t-Bu)³

Esters to aldehydes

DIBAL AlH(i-Bu)²

Acylchlorides to keytones

Cuprates R²CuLi

Eliminating carbonyls and C-C bind forming

Ph³P=CH² or CHR (Witting)


Cis if R is alkane


Trans if R is EWG

Protecting a diol

Acid and keytone for keytal


Remove with water in acid

Protecting individual alcohol

RSiCl in Et³N


Remove with n-Bu⁴NF