Haloalkanes and Haloarenes Lecture Flashcards

Vocabulary based flashcards identifying key classifications, reagents, and reaction mechanisms from the Haloalkanes and Haloarenes chapter.

Alkylic halide

A compound where a halogen is directly attached to an $sp^3$ hybridized carbon.

Arylic halide

Also called a phenylic halide, this is a compound where the halogen is attached to an $sp^2$ hybridized carbon of a benzene ring.

Benzylic carbon

An $sp^3$ hybridized carbon atom that is directly attached to a benzene ring.

Vinylic carbon

A carbon atom part of a double bond ($C=C$); halogens attached to this carbon are called vinyl halides.

Allylic carbon

The carbon atom adjacent to a double-bonded carbon ($sp^3$ carbon next to a $C=C$ bond).

Gemical (Gem) dihalogen

A dihalogen derivative where two halogen atoms are attached to the same carbon atom, also known as Alkyledene chloride.

Vicinal (Vic) dihalogen

A dihalogen derivative where two halogen atoms are attached to adjacent carbon atoms, also known as Alkylene dichloride.

Chloroform

A trihalogen derivative with the chemical formula $CHCl_3$.

Carbon tetrachloride

A tetrahalogen derivative with the chemical formula $CCl_4$.

Grooves-Reaction

A method using primary alcohols, $HCl$, and anhydrous $ZnCl_2$ to prepare alkyl chlorides.

Sn2 Mechanism

Substitution Nucleophilic Bimolecular; a one-step concerted process involving a transition state that leads to Walden Inversion of configuration.

Sn1 Mechanism

Substitution Nucleophilic Unimolecular; a two-step process involving the formation of a carbocation intermediate and leading to a racemized product.

Darzens Process

The reaction between an alcohol and thionyl chloride ($SOCl_2$), considered the best method for preparing alkyl halides because the side products ($SO_2$ and $HCl$) are gases.

Finkelstein's Reaction

A halogen exchange reaction where an alkyl chloride or bromide reacts with $NaI$ in acetone to produce an alkyl iodide.

Swarts Reaction

A reaction used to synthesize alkyl fluorides using metallic fluorides such as $AgF$, $Hg_2F_2$, $CoF_2$, or $SbF_3$.

NBS (N-Bromosuccinimide)

A reagent used for allylic bromination which follows a free radical mechanism.

Sandmeyer's Reaction

The preparation of aryl halides from benzene diazonium cation (BDC) using copper salts like $CuCl/HCl$ or $CuBr/HBr$.

Gattermann's Reaction

A preparation method for aryl halides from BDC using copper powder and an aqueous hydrogen halide ($HX$).

Balz-Schiemann Reaction

The conversion of benzene diazonium cation to aryl fluoride using fluoroboric acid ($HBF_4$).

Ambident Nucleophile

A nucleophile that contains two nucleophilic centers but can only attack through one center at a given time, such as $CN^-$ or $NO_2^-$.

Sni Mechanism

Substitution Nucleophilic Internal; a reaction mechanism leading to the retention of configuration.

SnAr Mechanism

Substitution Nucleophilic Aromatic; a mechanism for a substitution reaction on an aromatic ring that proceeds via a Meisenheimer complex.

Meisenheimer Complex

The anionic intermediate formed during Nucleophilic Aromatic Substitution ($SNAr$).

Dow's Process

The industrial preparation of phenol from chlorobenzene using $NaOH$ at $623 K$ and $300 atm$.

NGP

Short for Neighboring Group Participation; involves a substituent with a lone pair at the $\beta$-carbon assisting in substitution reactions.

Wurtz Reaction

A coupling reaction where two molecules of alkyl halide react with sodium in dry ether to form a higher symmetrical alkane.

Fittig Reaction

The coupling of two molecules of aryl halide using sodium in dry ether to form biphenyl.

Wurtz-Fittig Reaction

The reaction of one aryl halide and one alkyl halide with sodium in dry ether to produce an alkylbenzene.

Ulmann Reaction

The synthesis of biphenyl by heating aryl iodides in the presence of copper powder.

Grignard Reagent

An organometallic compound with the formula $R-Mg-X$, formed by reacting an alkyl halide with magnesium in dry ether.

Frankland's Reagent

An organozinc compound with the formula $R_2Zn$.

E1 Reaction

Elimination Unimolecular; a two-step process starting with carbocation formation, typically favored by high temperatures and polar protic solvents.

E2 Reaction

Elimination Bimolecular; a concerted one-step mechanism characterized by an antiperiplanar transition state.

Saytzeff Rule

A rule stating that in elimination reactions, the major product is the more substituted alkene.