Organic Chemistry

Chapter 4: Analyzing Organic Reactions

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Assuming an atom has a pair of electrons to donate, the ability of a species to donate that pair should be inversely proportional to ____.

A polar ____ solvent can participate in hydrogen bonding with a nucleophile.

A polar ____ solvent does not hydrogen bond to nucleophiles to a significant extent.

If ____ are present, an incoming nucleophile can make a bond with the electrophile without displacing the leaving group.

If empty orbitals are present, ____

The carboxylic acid derivatives are often ranked by electrophilicity. ____.

The carboxylic acid derivatives are often ranked by ____. Anhydrides are the most reactive, followed by carboxylic acids and esters, and th…

The bond breaks in such a way that the two bonding electrons divide equally between the two participating atoms or fragments, in the proces…

The bond breaks in such a way that ____, in the process called homolytic cleavage.

The bond breaks in such a way that the entire bonding electron pair is donated to one of the atoms, in the process called ____.

The bond breaks in such a way that ____, in the process called heterolytic cleavage.

In homolytic cleavage of bonds, ____ are formed.

In ____ cleavage of bonds, radicals are formed.

In heterolytic cleavage of bonds, ____ are formed.

In ____ cleavage of bonds, ions are formed.

____ are the molecular fragments that retain the electrons after heterolysis.

____ reactions are essentially the opposite of coordinate covalent bond formation.

Heterolytic reactions are essentially the opposite of ____ formation.

The best leaving groups will be able to ____

____ are more stable with an extra set of electrons and therefore make good leaving groups.

The conjugate bases of strong acids (like I – , Br – , and Cl – ) tend to make ____ leaving groups.

The conjugate bases of ____ acids (like I – , Br – , and Cl – ) tend to make good leaving groups.

Nucleophilic attack can occur when leaving group is just as reactive as the nucleophile. ____

In both ____ reactions, a nucleophile forms a bond with a substrate carbon and a leaving group leaves.

In both S N 1 and S N 2 reactions, ____

S N 1 reactions contain ____ step(s).

S N 2 reactions contain ____ step(s).

The first step of S N 1 is ____.

The second step in S N 1 reactions is ____.

The ____ substituted the carbocation, the more stable it is.

The more substituted the carbocation, the more stable it is because ____.

S N 1 rate of reaction can be represented by rate = ____.

____ rate of reaction can be represented by rate = k [R–L].

S N 2 rate of reaction can be represented by rate = ____.

____ rate of reaction can be represented by rate = k [Nu:][R–L].

S N 1 rate of reaction is determined by ____.

S N 2 rate of reaction is determined by ____.

S N 1 is a ____ order rate reaction.

S N 2 is a ____ order rate reaction.

____ reactions pass through a planar intermediate before the nucleophile attacks, the product will usually be a racemic mixture.

S N 1 reactions pass through ____ before the nucleophile attacks, the product will usually be a racemic mixture.

S N 1 reactions pass through a planar intermediate before the nucleophile attacks, the product will usually be ____.

A ____ reaction is a chemical reaction in which all bond breaking and bond making occurs in a single step(s).

A concerted reaction is a chemical reaction in which all bond breaking and bond making occurs in ____ step(s).

____ is a concerted reaction.

In S N 2 reactions, the nucleophile actively displaces the leaving group in a ____ attack.

In ____ reactions, the nucleophile actively displaces the leaving group in a backside attack.

For backside attack to occur, ____

The less substituted the carbon, the ____ reactive it is in S N 2 reactions.

____ reactions are accompanied by an inversion of relative configuration.

S N 2 reactions are accompanied by ____

____ reaction, one in which the configuration of the reactant determines the configuration of the product due to the reaction mechanism.

Stereospecific reaction, one in which ____

The S N 2 reaction is ____ and proceeds by backside displacement, thereby producing inversion of configuration at the reacting center.

The S N 2 reaction is stereospecific and proceeds by backside displacement, thereby producing ____.

The S N 2 reaction is stereospecific and proceeds by ____, thereby producing inversion of configuration at the reacting center.

In oxidation–reduction (redox) reactions , o____f the reactants change.

____ is an indicator of the hypothetical charge that an atom would have if all bonds were completely ionic.

Oxidation state is an indicator of ____.

Oxidation refers to an in____ oxidation state.

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