Master Reaction Chart: Starting Materials, Reagents, Products, and Purpose

Vocabulary flashcards summarizing the master reaction chart of starting materials, reagents, products, and functional transformations in organic chemistry.

Radical halogenation

A reaction converting an alkane (R-H) into an alkyl bromide or chloride using $Br_2$ / light ($h\nu$) or $Cl_2$ / light by replacing an H with Br or Cl.

SN1 substitution

A substitution reaction where the leaving group departs from usually a $3^\circ$ alkyl halide to form a carbocation intermediate, followed by nucleophilic attack using $H_2O$ or ROH to yield an alcohol or ether.

SN2 substitution

A one-step substitution reaction where a strong nucleophile (such as NaCN / DMSO or NaOH) replaces a leaving group on usually a methyl or $1^\circ$ alkyl halide to form a substituted molecule.

E1 elimination

An elimination reaction starting usually with a $3^\circ$ alkyl halide treated with $H_2O$ or ROH and heat, where the leaving group and beta H are removed via a carbocation intermediate to form an alkene.

E2 elimination

A concerted elimination reaction of an alkyl halide with a beta H using a strong base such as NaOEt / EtOH or KOtBu, removing a beta H as the leaving group departs to form an alkene.

NaBH4 reduction

A reduction reaction that changes a C=O carbonyl group of an aldehyde or ketone into a C-OH group using $NaBH_4$ / $CH_3OH$ to produce a $1^\circ$ or $2^\circ$ alcohol.

LiAlH4 reduction

A strong carbonyl reduction converting an aldehyde, ketone, or ester into alcohol(s) using 1. $LiAlH_4$ / ether followed by 2. $H_3O^+$.

PCC oxidation

An oxidation reaction using PCC / $CH_2Cl_2$ that oxidizes a $1^\circ$ or $2^\circ$ alcohol into an aldehyde or ketone, specifically stopping at the aldehyde for a $1^\circ$ alcohol.

Jones oxidation

An oxidation reaction using $CrO_3$ / $H_2SO_4$ / $H_2O$ that oxidizes a $1^\circ$ alcohol to a carboxylic acid and a $2^\circ$ alcohol to a ketone.

Grignard addition

A reaction converting an aldehyde, ketone, or ester into an alcohol by forming a new carbon-carbon bond at the carbonyl using 1. RMgBr / ether followed by 2. HCl / $H_2O$.

PBr3 substitution

A substitution reaction that replaces an OH group with Br on a $1^\circ$ or $2^\circ$ alcohol using $PBr_3$ to yield an alkyl bromide.

SOCl2 substitution

A substitution reaction that replaces an OH group with Cl on a $1^\circ$ or $2^\circ$ alcohol using $SOCl_2$ / base ($Et_3N$) to produce an alkyl chloride.

Acid halide conversion

A reaction converting an alcohol into an alkyl halide using HBr or HCl, which replaces the OH group with Br or Cl.

Tosylation

A reaction converting an alcohol into an alkyl tosylate (R-OTs) using TsCl / pyridine or $Et_3N$, which transforms the OH group into a good leaving group.

Alcohol dehydration

An elimination reaction that removes water from an alcohol using $H_2SO_4$ or $H_3PO_4$ with heat to form an alkene (C=C).