Organic Chemistry Chap 8

Front 1

What compounds are in Group III?

Back 1

all families have electronegative atom or an electron-withdrawing group attached to an sp3 carbon, which creates a polar bond that allows the compound to undergo substitution and/or elimination reactions

Front 2

How would the following compounds react in a substitution versus an elimination reaction?

RCH2CH2X + Y-

Back 2

Front 3

Leaving Group

Back 3

the atom or group that is substituted or eliminated

Front 4

A better leaving group is (harder/easier) to substitute or eliminate from a compound.

Back 4

A better leaving group is easier to substitute or eliminate from a compound.

Front 5

Nucleophilic Substitution Reaction

Back 5

a reaction in which the nucleophile substitutes for an atom or group

Front 6

Rate Constant

Back 6

written k, a measure of how easy or difficult it is to reach the transition state of a reaction (to get over the energy barrier)

Front 7

Bimolecular Reaction

Back 7

a reaction in which two molecules are involved in the transition of the rate-determining step (the slowest one)

Front 8

An SN2 reaction is a (one-step/two-step) reaction that results in (inverted/identical/mixed) configuration.

Back 8

An SN2 reaction is a one-step reaction that results in inverted configuration.

Front 9

In the mechanism for an SN2 reaction of an alkyl halide, a(n) _____________ attacks the (front/back) side of the carbon that is bonded to the leaving group.

Back 9

In the mechanism for an SN2 reaction of an alkyl halide, a nucleophile attacks the back side of the carbon that is bonded to the leaving group.

Front 10

Steric Effects

Back 10

effects due to the fact that groups occupy a certain volume of space

Front 11

Steric Hindrance

Back 11

refers to bulky groups at the site of a reaction that makes it difficult for reactants to approach each other

Front 12

The relative lack of _________________________ causes methyl halides and primary alkyl halides to be the most reactive in SN2 reactions.

Back 12

The relative lack of steric hindrance causes methyl halides and primary alkyl halides to be the most reactive in SN2 reactions.

Front 13

When comparing bases of the same type, the weaker the basicity of a group (the (bigger/smaller) its pK_a value), the (better/worse) is its leaving propensity.

Back 13

When comparing bases of the same type, the weaker the basicity of a group (the bigger its pK_a value), the better is its leaving propensity.

Front 14

Rate the reactivities of the following:

RCl

RBr

RF

RI

Back 14

RI > RBr > RCl > RF

Front 15

The weaker the base, the (more/less) stable the compound and the (better/worse) it is as a leaving group.

Back 15

The weaker the base, the more stable the compound and the better it is as a leaving group.

Front 16

Basicity

Back 16

a measure of how well a compound shares its lone pair with a proton; the stronger the base, the better it shares

Front 17

Nucleophilicity

Back 17

a measure of how readily a compound is able to attack an electron-deficient atom

Front 18

The better the nucleophile, the (faster/slower) the rate of an SN2 reaction.

Back 18

The better the nucleophile, the faster the rate of an SN2 reaction.

Front 19

Stronger bases are (better/worse) nucleophiles and so will lead to (SN1/SN2) and (E1/E2) reactions.

Back 19

Stronger bases are better nucleophiles and so will lead to SN2 and E2 reactions.

Front 20

Nucleophilicity (is/is not) affected by steric effects. Basicity (is/is not) affected by steric effects.

Back 20

Nucleophilicity is affected by steric effects. Basicity is not affected by steric effects.

Front 21

An SN1 reaction is a (one-step/two-step) reaction that results in (identical/inverted/both) configuration(s).

Back 21

An SN1 reaction is a two-step reaction that results in both configurations.

Front 22

If the leaving group is attached to a(n) _______________________________, an SN1 reaction forms a pair of enantiomers and an SN2 reaction forms an (inverted/identical) molecule.

Back 22

If the leaving group is attached to an asymmetric/chiral center, an SN1 reaction forms a pair of enantiomers and an SN2 reaction forms an inverted molecule.

Front 23

Solvolysis

Back 23

reaction with a solvent

Front 24

Bifunctional Molecule

Back 24

a molecule with two functional groups (e.g., ester)

Front 25

A reaction between two separate molecules is called (intermolecular/intramolecular).

Back 25

A reaction between two separate molecules is called intermolecular.

Front 26

A reaction between two parts of the same molecule is called (intermolecular/intramolecular).

Back 26

A reaction between two parts of the same molecule is called intramolecular,

Front 27

(Three/Five)- and (four/six)-membered rings are strained, making them less stable.

Back 27

Three- and four-membered rings are strained, making them less stable.

Front 28

A (low/high) concentration of reactant favors an intramolecular reaction because...

Back 28

A low concentration of reactant favors an intramolecular reaction because the functional groups of the same molecule are more likely to collide in the proper orientation.

Front 29

In rings larger than ______ carbons, the likelihood of functional groups in the same molecule colliding decreases sharply; thus, (intramolecular/intermolecular) reactions are favored for large molecules.

Back 29

In rings larger than seven carbons, the likelihood of functional groups in the same molecule colliding decreases sharply; thus, intermolecular reactions are favored for large molecules.

Front 30

Epoxide

Back 30

an ether in which the oxygen is incorporated into a three-membered ring

Front 31

Elimination Reaction

Back 31

a reaction that involves the elimination of atoms (or molecules) from the reactant

Front 32

The product of an elimination reaction is a(n) ____________________.

Back 32

The product of an elimination reaction is an alkene.

Front 33

E2 Reaction

Back 33

an elimination reaction with a bimolecular transition state

Front 34

Beta-Carbon

Back 34

a carbon adjacent to an alpha-carbon

Front 35

Alpha-Carbon

Back 35

a carbon bonded to a halogen

Front 36

E1 Reaction

Back 36

an elimination reaction with a unimolecular transition state

Front 37

Regioselective reactions produce (equal/unequal) amounts of constitutional isomers.

Back 37

Regioselective reactions produce unequal amounts of constitutional isomers.

Front 38

The major product of an E2 reaction is generally the (more/less) stable alkene.

Back 38

The major product of an E2 reaction is generally the more stable alkene.

Front 39

Stereoselective Reaction

Back 39

a reaction which forms more of one stereoisomer than of another

Front 40

E1 and E2 reactions are stereoselective and thus produce (equal/unequal) amounts of stereoisomer products.

Back 40

E1 and E2 reactions are stereoselective and thus produce unequal amounts of stereoisomer products.

Front 41

The major product of E1 and E2 reactions is the (more/less) stable stereoisomer, which has less __________ strain, which is (cis/trans) or (E/Z).

Back 41

The major product of E1 and E2 reactions is the more stable stereoisomer, which has less steric strain, which is trans or E.

Front 42

What factors determine whether SN2/E2 or SN1/E1 reactions take place?

Back 42

1. Halide configuration (methyl, primary, secondary, tertiary)

2. Strength of nucleophile

3. Strength of base

4. polar protic solvent = elimination; polar aprotic solvent = substitution

Front 43

If a reactant that participates in the rate-determining step is charged, increasing the polarity of the solvent will (increase/decrease/not affect) the rate of the reaction.

Back 43

If a reactant that participates in the rate-determining step is charged, increasing the polarity of the solvent will decrease the rate of the reaction.

Front 44

If none of the reactants that participates in the rate-determining step is charged, increasing the polarity of the solvent will (increase/decrease/not affect) the rate of the reaction.

Back 44

If none of the reactants that partipates in the rate-determining step is charged, increasing the polarity of the solvent will increase the rate of the reaction.

Front 45

The greater or more concentrated the charge on a molecule, the (stronger/weaker) will be its interactions with a polar solvent and the more the charge will be (stabilized/destabilized).

Back 45

The greater or more concentrated the charge on a molecule, the stronger will be its interactions with a polar solvent and the more the charge will be stabilized.

Front 46

A carboxylic acid will be a weaker acid in a solvent that is (more/less) polar than water.

Back 46

A carboxylic acid will be a weaker acid in a solvent that is less polar than water.

Front 47

Alkoxide Ion

Back 47

RO-

Front 48

Williamson Ether Synthesis

Back 48

formation of an ether (ROR) from the reaction of an alkoxide ion with an alkyl halide

Front 49

The Williamson ether synthesis reaction is an (SN1/SN2/E1/E2) reaction.

Back 49

The Williamson ether synthesis reaction is an SN2 reaction.

Front 50

In ether synthesis, the less hindered group should be provided by the (alkyl halide/alkoxide ion).

Back 50

In ether synthesis, the less hindered group should be provided by the alkyl halide.

Front 51

Zaitsev's Rule

Back 51

the proton in an elimination reaction is removed from the beta-carbon atom bonded to the fewest hydrogen atoms

Front 52

Back 52

Front 53

What mechanism will this use?

Back 53

E2

Front 54

What mechanism will this use?

Back 54

SN2 and E2

Front 55

Polar Protic Solvent

Back 55

1. Polar - molecules have partial charges due to differences in electronegativity (e.g., O-H bond)

2. Protic - have OH or NH bonds which can participate in hydrogen bonding

Front 56

Back 56