Organic Chemistry Reagents and Reactions

A collection of vocabulary flashcards covering organic chemistry reagents, reaction outcomes, and functional group transformations based on the lecture transcript.

$KMnO_4$ (cold)

Converts an alkene into a diol with 2 $OH$ groups added syn.

$KMnO_4$ (hot)

Causes alkene cleavage into a carboxylic acid or a ketone.

$$Na/NH_3$$

Reduces an alkyne to a trans alkene.

Lindlar catalyst

Makes a cis alkene from an alkyne.

$H_2O$, $H_2SO_4/HgSO_4$ (alkyne)

Converts an alkyne to a ketone via Markovnikov addition.

$$O_3 / Me_2S$$

Breaks an alkene double bond into aldehydes and/or ketones.

$$Br_2/CCl_4$$

Adds one $Br$ to each alkene carbon via anti addition.

$HCl$ (alkene)

Adds $H$ and $Cl$ to an alkene where $Cl$ goes to the more substituted carbon.

$EtOH/H^+$ (alkene)

Turns an alkene into an ether by adding $OEt$.

$Hg(OAc)_2$, $H_2O$ then $NaBH_4$, $OH^-$

Turns an alkene into a Markovnikov alcohol without rearranging.

$BH_3/THF$ then $H_2O_2/OH^-$

Turns an alkene into an anti-Markovnikov alcohol; for terminal alkynes, it gives an aldehyde.

$$Br_2/H_2O$$

Makes a halohydrin where the $OH$ is on the more substituted carbon and $Br$ is on the other.

$$Br_2/CH_3OH$$

Makes a bromoether where the $OCH_3$ is on the more substituted carbon and $Br$ is on the other.

$$H_2/Pt$$

Makes an alkane from an alkene or alkyne.

$$OsO_4/NMO$$

Adds 2 $OH$ groups to an alkene on the same side.

$NaBH_4/EtOH$, then $H^+$

Reduces aldehydes and ketones (but not esters) to alcohols.

$CrO_3/H^+$ (or $Na_2Cr_2O_7/H^+$)

Oxidizes a $1^{\circ}$ alcohol ($OH$) into a carboxylic acid ($COOH$).

$$PBr_3$$

Turns an $OH$ group into $Br$, which can then be swapped for $CN$ using $NaCN$.

$$SOCl_2$$

Turns an $OH$ into $Cl$; only works on carboxylic acids and $1,2$ alcohols.

$$ClSiMe_3$$

A protecting group that turns an $OH$ into $OSiMe_3$; removed by $H^+/H_2O$.

$$TfCl$$

Converts an $OH$ group into a much better leaving group ($OTf$).

Basic epoxide opening

The $OH$ ends up on the more substituted carbon.

Acidic epoxide opening

Puts the $OH$ on the less substituted carbon; does not work on carboxylic acids.

$$HCl/ZnCl_2$$

Turns an alcohol into an alkyl chloride; does not work on carboxylic acids.

$$TsCl$$

Converts an $OH$ group into a good leaving group ($OTs$).

$$HNO_3 / H_2SO_4$$

Adds a $NO_2$ group to an aromatic ring.

Clemmensen reduction

Uses $Zn(Hg)$ and $HCl$ to turn a carbonyl (aldehyde or ketone) into an alkane.

$CuBr$ (aromatic)

Swaps an $N_2^+$ group for $Br$ on a benzene ring.

$HONO$ (nitrous acid)

Converts a primary aromatic amine ($NH_2$ on benzene) into a diazonium salt ($N_2^+$).

$$H_2SO_4, H_3PO_4$$

Removes an $OH$ with a neighboring $H$ to create a double bond.

Alkene + $H_2SO_4$ (cold)

Adds $H$ and $OSO_3H$ across the double bond via Markovnikov addition.

$$K_2Cr_2O_7$$

A strong oxidizer that turns alcohols into carbonyl compounds or acids, and oxidizes benzene side chains into $COOH$.

$$SO_3/H_2SO_4$$

An EAS reaction that adds $-SO_3H$ to benzene (sulfonation), making the ring less reactive.

$$CH_3COCl$$

Protects an $NH_2$ group by making an amide.

$$NaNO_2/HCl$$

Converts $Ar-NH_2$ into a diazonium salt ($Ar-N_2^+Cl^-$) to allow replacement of the amine group.

$H_3PO_2$ (with diazonium)

Removes the $NH_2$ entirely from an aromatic ring and replaces it with $H$.

$$NH_2NH_2$$

Forms a hydrazone from a carbonyl; with base and heat, it fully reduces the carbonyl to a $CH_2$ group.

$$NaNH_2$$

Rips off the terminal alkyne $H$ to create an acetylide (carbon nucleophile).

$PPh_3$, $R-X$, then $n-BuLi$

Makes a ylide that changes a $C=O$ into a $C=C$ bond.

$TsOH/C_6H_6$ + heat

Removes water and acts as a carbonyl protecting group aid.

LDA (Lithium Diisopropylamide)

A strong, bulky base that removes the least hindered $\alpha$-hydrogen fastest to create an enolate.

$H_3O^+$ and heat

Converts esters into carboxylic acids via hydrolysis.