Exam 2 (Information)

Question 1

Double bonds separated by one single bond

Answer 1

Conjugated

Question 2

p orbitals on 3 or more C,N, or O atoms in a row in the same plane

Answer 2

Conjugated

Question 3

A compound containing two adjacent (next to) pi nonds

Answer 3

Cumulated

Question 4

Double bonds are

Answer 4

Nucleophilic and attack the electrophil

Question 5

The product that forms the fastest forms the most

Answer 5

Kinetic Control

Question 6

Equilibrium is asserted and the most stable product predominates over time

Answer 6

Thermodynamic Control

Question 7

A reaction for which the product distribution is determined by the relative rates at which the products are formed

Answer 7

Kinetic Control

Question 8

A reaction for which the ratio of products is determined solely b the distribution of energy among the products

Answer 8

Thermodynamic Control

Question 9

At low temperatures, only few molecules have energy greater than Ea (1,4) so most

Answer 9

1,2 products form

Question 10

At high temperatures, first 1,2 product is formed, THEN

Answer 10

1,2 product reforms the intermediate and an equilibrium forms and some starts forming 1,4 product and is stuck there. As time passes, more 1,4 product forms and will predominate.

Question 11

Mechanism-less Reaction

Answer 11

Pericyclic Reactions

Question 12

Most common pericyclic reaction

Answer 12

Cycloaddition (Diels-Alder)

Question 13

Pericyclic Reactions (3)

Answer 13

Cycloaddition (Diels-Alder), Electrocyclization, and Sigmatropic Rearrangement

Question 14

A bond theory that treats a bond as the sharing of electrons that are associated individual atoms, rather than bing associated with the entire molecule

Answer 14

Valence Bond Theory (partial charges)

Question 15

A description of bonding in terms of molecular orbitals, which are orbitals associated with an entire molecule rather than an individual atom

Answer 15

Molecular Orbital Theory (orbitals in and out of phase)

Question 16

Orbitals in phase

Answer 16

Bond

Question 17

Orbitals out of phase

Answer 17

Antibond or Repulsion

Question 18

The analysis of a reaction using Molecular Orbit Theory, where only the frontier orbitals (HOMO and LUMO) are considered

Answer 18

Frontier Orbital Theory

Question 19

The highest occupied molecular orbital

Answer 19

HOMO

Question 20

The lowest unoccupied molecular orbital

Answer 20

LUMO

Question 21

The highest occupied molecular orbital and the lowest unoccupied molecular orbital that participate in a reaction

Answer 21

Frontier orbitals

Question 22

Dienes and dienophiles form no reaction when

Answer 22

only heat is present

Question 23

[4+2] Cycloaddition

Answer 23

Diels Alder

Question 24

hv changes

Answer 24

HOMO and LUMO

Question 25

A compound that possesses chirality centers and an internal plane of symmetry

Answer 25

meso compound

Question 26

A cis dienophile added to a cis diene

Answer 26

makes a meso compound

Question 27

A cis diene added to a trans dienophile

Answer 27

makes enatiomers (2 products)

Question 28

Other functional groups that can be dienophiles

Answer 28

C trpl C, C trpl N

Question 29

In Diels Alder reactions that produce bicyclic structures, the positions that are anti to the larger bridge

Answer 29

exo

Question 30

In Diels Alder reactions that produce bicyclic structures, the positions that are syn to the larger bridge

Answer 30

endo

Question 31

Trans to each other, lower energy, thermodynamic product at hight temp, higher Ea, no pi stacking

Answer 31

Exo

Question 32

Two groups pointing toward each other, Kinetic product (forms faster), cold, Lower Ea due to pi stacking

Answer 32

Endo

Question 33

Lower energy put off

Answer 33

more stable

Question 34

Aromatic if:

Answer 34

1. Cyclic 2. Every atom in ring must be part of the same conjugated system 3. Huckels rule: 4n+2=pi e- (n must be whole number)

Question 35

Obeys rules one and two of aromaticity rules but not three

Answer 35

Antiaromatic

Question 36

For antiaromatic to be stable

Answer 36

it resists conjugation and is flat

Question 37

Aromatic structures that contain N, O, S, NH, or a lone pair

Answer 37

Heteroaromatic Compounds

Question 38

Compounds containing multiple aromatic rings fused together

Answer 38

Polycyclic Aromatic Hydrocarbons (PAHs)

Question 39

1,2 substituents

Answer 39

Ortho-

Question 40

1,3 substituents

Answer 40

Meta-

Question 41

1,4 substituents

Answer 41

Para-

Question 42

A substitution reaction in which an aromatic proton is replaced by an electrophile and the aromatic moiety is preserved

Answer 42

Electrophilic Aromatic Substitution (EAS)

Question 43

A compound capable of functioning as an electron pair acceptor

Answer 43

Lewis Acid

Question 44

The positively charged intermediate of an electrophilic aromatic substitution reaction

Answer 44

Sigma Complex

Question 45

An electrophilic aromatic substitution reaction in which an SO3H group is installed on an aromatic ring

Answer 45

Sulfonation

Question 46

An electrophilic aromatic substitution reaction that involves the installation of a nitro group (NO2) on an aromatic ring

Answer 46

Nitration

Question 47

An electrophilic aromatic substitution reaction that installs an acyl group on an aromatic ring

Answer 47

Friedel-Crafts Acylation

Question 48

The term describing a carbonyl group (C=O) connected to an alkyl group (no pi bonds; only C and H) or an aryl group (aromatic ring)

Answer 48

Acyl Group

Question 49

An electrophilic aromatic substitution reaction that installs an alkyl group on an aromatic ring

Answer 49

Friedel-Crafts Alkylation

Question 50

A substituent lacking pi bonds and comprised of only carbon and hydrogen atoms

Answer 50

Alkyl

Question 51

Transition metals + Acid =

Answer 51

Good Reducing Agents | Ex) Br2/FeBr3 - - Only adds O and P

Question 52

Electron Poor, Electron Withdrawing Group

Answer 52

Deactivated | Ex) N(+)O2

Question 53

Electron Rich, Electron Donating Group

Answer 53

Activating | Ex) N(lone pair)H2

Question 54

Usually deactivating | Meta Directing

Answer 54

Electron Withdrawing Groups (EWGs)

Question 55

Usually activating | Ortho and Para Directing

Answer 55

Electron Donating Groups (EDGs)

Question 56

If atom attached to ring is + charged

Answer 56

Strongly Deactivating

Question 57

If atom attached to ring has a partial + charge due to resonance

Answer 57

Moderately Deactivating

Question 58

If atom attached to benzene has a lone pair

Answer 58

Strongly activating

Question 59

Alkyl groups

Answer 59

Weakly activating

Question 60

Deactivating groups can only add

Answer 60

one at a time

Question 61

Strong electron withdrawing group (resonance stabilized )

Answer 61

SNAr

Question 62

Elimination/Addition (Dow Process)

Answer 62

Benzyne (No strong EWGs)

Question 63

Nu- (either NH2 or OH or OR) | NO2 and CL

Answer 63

SNAr

Question 64

Cl | Can do Diels Alder

Answer 64

Benzyne

Question 65

The withdrawal of electron density that occurs when a bond is shared by two atoms of differing electronegativity

Answer 65

Induction

Question 66

Increase up and to the right on the periodic table

Answer 66

Electronegativity