Organic Chemistry Final Review

Comprehensive vocabulary and reagent flashcards for Alkenes, Alkynes, EAS, Carbonyls, and Carboxylic Acids based on the Organic Chemistry final review notes.

Markovnikov's Rule

A rule in alkene addition where the $X$ group (from $HX$) goes to the more substituted carbon.

Anti-addition

A stereochemical outcome where groups add to opposite sides of a molecule, occurring during the formation of a 1,2-Dihalide from an alkene and $X_2$ ($Br_2$, $Cl_2$).

Oxymercuration-Demercuration

A process involving $1.{ }Hg(OAc)_2,H_2O/2.NaBH_4$ that converts an alkene into an alcohol with Markovnikov selectivity and no carbocation rearrangements.

Hydroboration-Oxidation

A process involving $1. { }BH_3, THF / 2. { }H_2O_2, NaOH$ that converts an alkene into an alcohol with Anti-Markovnikov selectivity and syn-addition.

Oxidative Cleavage

A reaction using $1.O_3/2.{ }Zn,H_3O^{+}$ that cuts a double bond in half to produce aldehydes or ketones.

Alkyne Hydration (Markovnikov)

The reaction of an alkyne with $H_2O, H_2SO_4$, and $HgSO_4$ to form a methyl ketone via tautomerization from an enol to a keto form.

Lindlar Catalyst

A reagent used with $H_2$ for the syn-addition of hydrogen to an alkyne, stopping the reaction at a cis-alkene.

Dissolving Metal Reduction

The reduction of an alkyne using $Li / Na, NH_3(l)$ to produce a trans-alkene.

EAS Halogenation

The addition of $-Br$ or $-Cl$ to an aromatic ring using $Br_2, FeBr_3$ or $Cl_2, FeCl_3$.

Nitration

The addition of a $-NO_2$ group to an aromatic ring using $HNO_3$ and $H_2SO_4$.

Sulfonation

The addition of a $-SO_3H$ group to an aromatic ring using $SO_3$ and $H_2SO_4$.

Friedel-Crafts Alkylation

The reaction of an aromatic ring with $R-Cl$ and $AlCl_3$; requires monitoring for carbocation rearrangements.

Friedel-Crafts Acylation

The addition of an $-COR$ group to an aromatic ring using $RCOCl$ and $AlCl_3$; involves no rearrangements and deactivates the ring.

Benzoic Acid Formation (from Alkylbenzene)

The oxidation of an alkylbenzene using $KMnO_4$ and $H_3O^+$, which only occurs if there is a benzylic hydrogen.

PCC (Pyridinium Chlorochromate)

A reagent for mild oxidation that stops the conversion of a primary (1°) alcohol at the aldehyde stage.

Jones Reagent

The combination of $CrO_3$ and $H_3O^+$ used for strong oxidation of a primary (1°) alcohol to a carboxylic acid.

NaBH4

A mild reducing agent that converts aldehydes or ketones to alcohols but does NOT reduce esters or carboxylic acids.

LiAlH4 (LAH)

A strong reducing agent that reduces aldehydes, ketones, esters, and carboxylic acids to primary alcohols.

Grignard Reagent ($RMgX$)

A reagent that reacts with aldehydes or ketones to add an R-group, create a new $C-C$ bond, and form an alcohol.

Wittig Reaction

A reaction using $Ph_3P=CR_2$ where the $C=O$ of an aldehyde is replaced by a $C=C$ to produce an alkene.

Reactivity Ladder

The order of reactivity for carboxylic acid derivatives: Acid Chloride > Anhydride > Ester/Acid > Amide.

Zaitsev's Rule

During an elimination reaction, the most substituted alkene is the major product.

O/P Directors

EAS starting groups that direct incoming substituents to the ortho or para positions, including $-NH_2, -OH, -OR, -R$, and Halogens (deactivators).

Meta Directors

EAS starting groups that direct incoming substituents to the meta position, including $-NO_2, -CN, -CHO, -COOH$, and $-SO_3H$.