Organic Chemistry Transformations: Alcohols, Alkenes, and Carbonyls

Flashcards covering various chemical transformation types, specific reagents, and special reaction notes for alcohols, alkenes, halides, and carbonyls.

$-X \rightarrow -OH$ (Substitution)

Reagents: $KOH$ or $NaOH$. Notes: $1^\circ$ alcohols only (why not $2^\circ$ or $3^\circ$?).

$C=C \rightarrow -OH$ (Acid-Catalyzed Hydration)

Reagents: $H_2O$, $H_2SO_4$. Notes: Adds $H$, $OH$ Markovnikov.

$C=C \rightarrow -OH$ (Oxymercuration-Demercuration)

Reagents: 1. $Hg(OAc)_2, H_2O$ 2. $NaBH_4$. Notes: Adds $H$, $OH$ Markovnikov.

$C=C \rightarrow -OH$ (Hydroboration-Oxidation)

Reagents: 1. $BH_3$ 2. $NaOH, H_2O_2$. Notes: Adds $H$, $OH$, Non-Markovnikov, Syn.

$C=O \rightarrow -OH$ (Reduction)

Reagents: $LAH$ or $NaBH_4$. Notes: $NaBH_4$ is selective for ald/ketones only.

$C=O \rightarrow -OH$ (Organometallic Addition)

Reagents: $RMgBr$ or $RLi$. Notes: Adds 1x to ald/ketones; Adds 2x to esters (Why?); Doesn’t react with C. Acids (Why?).

$-OH \rightarrow -OMs$ or $-OTs$ (Sulfonylation)

Reagents: $MsCl$ or $TsCl$, pyridine. Notes: No inversion occurs.

$-OH \rightarrow -X$ ($S_N1$)

Reagents: $HX$. Notes: $3^\circ$ alcohols only.

$-OH \rightarrow -X$ (Primary/Secondary Substitution)

Reagents: $PBr_3$ or $SOCl_2$, pyridine. Notes: $1^\circ$ or $2^\circ$ alcohols only (inversion).

$-OH \rightarrow C=C$ (Acid-Catalyzed Dehydration)

Reagents: $H_2SO_4$ or $H_3PO_4$ and heat. Notes: $2^\circ$ or $3^\circ$ alcohols only (beware of rearrangements).

$-OH \rightarrow C=C$ (Base-Mediated Elimination)

Reagents: $POCl_3$, pyridine. Notes: $2^\circ$ or $3^\circ$ alcohols only.

$-OH \rightarrow C=O$ (Oxidation)

Reagents: $KMnO_4, H_2O$; $Na_2Cr_2O_7, H_3O^+$; $CrO_3, H_2SO_4, H_2O$; $PCC$. Notes: $2^\circ$ alcohols form ketones; $1^\circ$ alcohols form either c. acids or aldehydes.