Organic Chemistry 1 and 2 Reactions

Detailed collection of organic chemistry reactions including reagents, conditions, and resulting transformations derived from practice notes.

(Epoxide) 1) $NaSH$ 2) $H_2O$

Epoxide to Alcohol and Thiol

$$HX$$

Turns Double Bond into Addition of $X$ at MarkovNikov position

$HBr$, $ROOR$

Turns Double Bond into Addition of $X$ at Anti-MarkovNikov position

$$H_3O^+$$

Turns Double Bond into Addition of Alcohol at MarkovNikov position

1) $Hg(OAc)_2$, $H_2O$ 2) $NaBH_4$

Turns Double Bond into Addition of Alcohol at MarkovNikov position

1) $BH_3$, $THF$ 2) $H_2O_2$, $NaOH$

Turns Double Bond into Addition of Alcohol at Anti-MarkovNikov position with stereo-chemistry

$H_2$, $Pt$

Reduces Double Bond to Single Bond

$$Br_2$$

Brominates both double bond positions

$Br_2$, $H_2O$

Brominates Anti-MarkovNikov Position, and adds Alcohol at MarkovNikov Postion (Opposite Stereo Chemistry)

1) $RCO_3H$ 2) $H_3O^+$

Adds Alcohol to both double bond positions (Opposite Stereo Chemistry)

$KMnO_4$, $NaOH$ cold

Adds Alcohol to both double bond positions (Same Stereo Chemistry)

1) $OsO_4$ 2) $NaHSO_3$, $H_2O$

Adds Alcohol to both double bond positions (Same Stereo Chemistry)

1) $O_3$ 2) $DMS$

Splits Molecule at Double Bond site and adds Oxygen to both openings

1) $xs$ $NaNH_2$ 2) $H_2O$

Makes two Possible products: One only puts halogen on MarkovNikov Position, and other puts on halogen on each side of triple bond, completely reduces triple bond

$xs$ $HX$

Puts two halogens on MarkovNikov Position, completely reduces triple bond

$$HX$$

Puts Halogen at MarkovNikov Position, but only reduces bond a little bit

$H_2SO_4$, $H_2O$, $HgSO_4$

Adds Ketone at MarkovNikov Position

1) $R_2BH$ 2) $H_2O_2$, $NaOH$

Triple Bond to Aldehyde

$X_2$ (one equivalent) $CCl_4$

Triple Bond reduced to double bond (trans)

Excess $X_2$ $CCl_4$

Reduces triple bond completely, and adds four halogens, two on each side

1) $O_3$ 2) $H_2O$

Splits triple bond in half, and adds Carboxylic Acid plus $O=C=O$

$NaNH_2$ $RX$

Adds Group to other side of triple bond

1) $NaNH_2$ 2) $RX$ 3) $NaNH_3(l)$

Triple Bond to Double Bond (Trans)

1) $NaNH_2$ 2) $RX$ 3) $H_2$, $Pt$

Triple Bond to Single Bond (Trans)

1) $NaNH_2$ 2) $RX$ 3) $H_2$, Lindlar's Catalyst

Triple Bond to Double Bond (Cis)

1) $MCPBA$ 2) $H_3O^+$

Double Bond to double substituted Alcohols

$OsO_4$ $NMO$

Adds StereoChemistry and two Alcohols on each side of double bond (Catalytic)

$HBr$, $t\text{-}BuOk$

Moves double bond from middle to end

$HBr$ $NaOMe$

Moves double bond from edge to middle

$HBr$, $ROOR$, $t\text{-}BuOk$

Moves double bond from middle to end

$$NaOH$$

Primary Halogen to Primary Alcohol

$CH_3OH$, Heat

Tertiary Halogen to Tertiary Alcohol

$[H_2SO_4]$ $H_2O$

Double bond to MarkovNikov Alcohol

$H_2$ $Pd/C$

$O=C$ to $C$ single bond Alcohol

$NaBH_4$ + $EtOH$, $MeOH$, or $H_2O$

Alcohol added on Least Substituted Position on double bond

1) $LAH$ 2) $H_2O$

Ketone to Alcohol (With excess, all ketones turn into alcohols)

$NaBH_4$ $CH_3CH$

All Ketones to All Alcohols

1) $MCPBA$ 2) $OH^-$ or $H_3O^+$

Double bond to two alcohols (trans)

1) $OsO_4$ 2) $NaHSO_3$ or $KMnO_4$

Double bond to two alcohols (cis)

$Mg^\text{o}$ (Grignards)

Putting magnesium in between halogen and rest of molecule

1) $CH_3MgBr$ 2) $H_2O$ (Grignards)

Ketone to alcohol + methyl (with excess, ether and everything after become one methyl)

$TMSCl$ $Et_3N$

Alcohol to Oxygen + Silicon (Protecting)

$$TBAF$$

Takes off Silicon and makes it back to alcohol

$$HBr$$

Single Bond Alcohol to Single Bond Bromine (can be primary or tertiary)

$TsCl$, $X^-$

Secondary Alcohol to secondary halogen

$SOCl_2$ and Pyridine (Benzene with a N)

Primary Alcohol to Primary Chlorine

$PBr_3$ and Pyridine

Primary Alcohol to Primary Bromine

$H_2SO_4$, heat and $POCl_3$, $0^\text{o}$, and Pyridine

Alcohol to Alkene

$CrO_3$, $H_3O^+$, Acetone

Alcohol to Ketone

$Na_2Cr_2O_7$, $H_2SO_4$, $H_2O$

Alcohol to Carboxylic Acid

$PCC$, $CH_2Cl_2$

Alcohol to Aldehyde

$Na_2Cr_2O_7$, $H_2SO_4$, $H_2O$ (Benzene variant)

Benzene Alcohol to Benzoquinone

$H_2SO_4$ OR 1) $NaH$ 2) $RX$

Alcohol to Ether

$xs$ $HX$ heat

Ether to Halogen and Water

$$O_2$$

Ether to Ether + Peroxide

$$MCPBA$$

Alkene to Epoxide

1) $Br_2$, $H_2O$ 2) $NaOH$

Alkene to Double Alcohols or Epoxide

(Epoxide) 1) $NaOH$ 2) $H_2O$

Epoxide to double Alcohol

(Epoxide) 1) $LAH$ 2) $H_2O$

Epoxide to Alcohol and Hydrogen

(Epoxide) 1) $RMgBr$ 2) $H_2O$

Epoxide to Alcohol and $R$ group

(Epoxide) 1) $NaCN$ 2) $H_2O$

Epoxide to Alcohol and Nitrile

(Epoxide) 1) $NaRO$ 2) $H_2O$

Epoxide to Alcohol and Single Bond Oxygen plus $R$ group

(Epoxide) $HX$

Epoxide to Alcohol and Halogen

(Epoxide) $[H_3O^+]$, $ROH$

Epoxide to Alcohol and Single Bond Oxygen plus $R$ group

$NaOH/H_2O$, $Br_2$

Thiol to DiSulfide

$NaOH$, $RX$

Thiol to MonoSulifide

$NaIO_4$ (Oxidizing Agent)

Sulfide to Sulfoxide

$$H_2O_2$$

Sulfoxide to Sulfone

1 eq $HBr$

Alkene to $Br$

Diene + Dienophile

1-Hexene and $R$ groups (trans or cis)

Diene + Alkyne

HexaDiene and $R$ groups

Cyclopentene + Diene

Special Product (See Picture)

$Na_2Cr_2O_7$, $H_2SO_4$, $H_2O$ (Plain Benzene)

NO REACTION

$Na_2Cr_2O_7$, $H_2SO_4$, $H_2O$ (Substituted Benzene)

Benzene with Substituent that has a Benzylic Hydrogen to Benzene with Carboxylic Acid

$H_2O$, heat OR $NaOH$ (for Benzene substituents)

Benzene with Bromine Substituent to Benzene with Alcohol Substituent

$H_2SO_4$, heat OR $KO^+Bu$ (for Benzene substituents)

Benzene with Leaving Group Substituent to Benzene with Double Bond

$Pt$ or $Pd/C$, $H_2$ (on Benzene Ring)

NO REACTION

$Ni$, $H_2$, $100\text{ atm}$, $150^\text{o}C$

Benzene to CycloHexaDiene

$NBS$, heat

Addition of $Br$ group to Benzene substituent

$Pd/C$, $H_2$ (for Benzene substituent)

Benzene Alkene Substituent reduced to Alkane

$Na^\text{o}$, $CH_3OH$, $NH_3$

Benzene to CycloHexaDiene

$FeBr_3$, $Br_2$ (or $AlBr_3$, $Br_2$)

Benzene to Benzene with $Br$ substituent

$FeCl_3$, $Cl_2$ (or $AlCl_3$, $Cl_2$)

Benzene to Benzene with $Cl$ substituent

$H_2SO_4$, heat $\text{Δ}$ (Fuming $H_2SO_4$)

Benzene to Benzene with $SO_3H$ substituent

$HNO_3$, $H_2SO_4$

Benzene to Benzene with $NO_2$ substituent

$Fe$ or $Zn$, $HCl$ (or 1)$HNO_3/H_2SO_4$ 2) $Zn$, $HCl$ or $Pd/C$, $H_2$)

Benzene with $NO_2$ substituent to Benzene with $NH_2$ substituent

$R\text{-}Cl$, $AlCl_3$

Benzene to Benzene with $R$ group

$$ClCOR$$

Benzene to Benzene with Ketone and $R$ substituents

$Zn(Hg)$, $HCl$, $\text{Δ}$ (or $Pd/C$, $H_2$)

Benzene with Ketone and $R$ substituents to only $R$ substituent

$$9\text{-}BBN$$

Triple Bond to Aldehyde

$HNO_3$, $H_2SO_4$ (SLOW)

Benzene to Benzene with $NO_2$ or Toluene to Toluene with $NO_2$ sticking out (25x Faster)

$HNO_3$, $H_2SO_4$ (on Nitrobenzene)

Nitrobenezene to NO REACTION!

$ClCOCH_3$ $AlCl_3$ (on Benzene)

Benzene to Benzene with Ether Substituent

$ClCOCH_3$ $AlCl_3$ (on Benzene with Ether Substituent)

Benzene with Ether Substituent to NO REACTION!

1) $NaOH$ $70^\text{o}C$ 2) $H_3O^+$

Leaving Group is replaced with and alcohol on a benzene ring with $NO_2$ substituent in the para position

1) $ClCOR$ 2) $AlCl_3$

Benzene to $RC=O$ substituent

1) $NaOH$ $70^\text{o}C$ 2) $H_3O^+$ (Meta substituent)

Leaving Group with Electron Withdrawing Group at meta position to No Reaction

1) $NaOH$ $70^\text{o}C$ 2) $H_3O^+$ (Ortho substituent)

Leaving Group with Electron Withdrawing Group at ortho to cyclohexane with alcohol in place of the leaving group and Electron Withdrawing Group stays put

1) $NaOH$ $350^\text{o}C$ 2) $H_3O^+$

Benzene with $Cl$ to Benzene with $OH$

1) $NaNH_2$, $NH_3 (l)$ 2) $H_3O^+$

Benzene with $Cl$ to Benzene with $NH_2$