OChem final

Question 1

down carbon wedge for fisher projection

Answer 1

right

Question 2

endergonic

Answer 2

reaction favors reactants (G>0)

Question 3

during proton transfer/carbocation transfer avoid these 3 things

Answer 3

strong acid in base vice versa
intramolecular proton transfer
termolecular steps (three molecules in one step)

Question 4

energy diagram

Answer 4

go over notes chapter 8

Question 5

electrophile

Answer 5

electron poor

Question 6

exergonic

Answer 6

reaction favor products (G<0)

Question 7

sn1 and stereochemistry

Answer 7

not stereospecific
50:50 mixture of wedge and dash

Question 8

lower gibbs free energy corresponds to

Answer 8

greater stability

Question 9

strength of IMF

Answer 9

LDF, dipole-dipole, H-bond, Ion-dipole, ion-ion

Question 10

for species on the same row, nucleophilicity increases from…

Answer 10

right to left
F<OH<NH2

Question 11

polar aprotic solvents favor

Answer 11

Sn2 and E2

Question 12

polar protic solvents favor

Answer 12

Sn1 and E1

Question 13

Avoid incompatible acid and bases during proton transfer/carbocation rearrangements

Answer 13

strong bases can’t appear under acidic conditions
strong acids can’t appear under basic conditions

Question 14

leaving group ability increases as

Answer 14

charge stability increases

Question 15

dextrorotary

Answer 15

rotate light clockwise (+)

Question 16

E2 mechanism

Answer 16

base attacks beta hydrogen, creating a double bond and kicking out leaving group

Question 17

up carbon wedge for fisher projection

Answer 17

left

Question 18

polyhalogenation

Answer 18

Basic conditions
all alpha hydrogens are replaced

Question 19

Sn2 mechanism

Answer 19

nucleophile kicks off leaving group

Question 20

strong nucleophile favors

Answer 20

sn2

Question 21

E2 and stereochemisty

Answer 21

leaving group and leaving H must be antiperiplanar
newman projection

Question 22

strong, bulky bases favor

Answer 22

E2 over Sn2 due to steric hinderance

Question 23

three factors that affect light rotation

Answer 23

1. ability of the molecule to rotate light
2. concentration of molecule, as concentration increases rotation increases
3. path length, as path length increases rotation increases

Question 24

Rate law of Sn2 and E2

Answer 24

depend on reactant and nucleophile/base

Question 25

degree of unsaturation formula

Answer 25

(C(2)-H-X+N+2)/2

Question 26

when reacting with cl2, br2, or i2 under basic conditions

Answer 26

all alpha hydrogens are replaced with halogen

Question 27

weak base favors

Answer 27

E1

Question 28

pka of H2O and H3O

Answer 28

H2O = 14 H3O = 0

Question 29

study page 17, chapter 9

Answer 29

study page 17, chapter 9

Question 30

side of the reaction that's favored has lower...

Answer 30

Gibbs free energy

Question 31

antiperiplanar

Answer 31

understand how to do Newman projection

Question 32

halogenation rate in acidic conditions

Answer 32

halogen increase = rate decrease

Question 33

weak nucleophile favors

Answer 33

sn1

Question 34

in chair flip axial down becomes...

Answer 34

equatorial down and vice versa

Question 35

atoms in same column when comparing acidity

Answer 35

compare size larger atom means stronger acid size increases going down

Question 36

halogenation under acidic conditions

Answer 36

only a single alpha hydrogen is replaced

Question 37

epoxides are protonated under

Answer 37

acid conditions

Question 38

hydrogen donar

Answer 38

N, O, F with H bond

Question 39

atoms in same row when comparing acidity

Answer 39

compare EN acid strength goes up as EN goes up (F>O>N>C)

Question 40

fisher projection

Answer 40

the T one

Question 41

enthalpy

Answer 41

heat absorbed/released by a reaction

Question 42

for species on the same column, nucleophilicity increase from...

Answer 42

top to bottom F

Question 43

E1 mechanism

Answer 43

leaving group leaves on its own and creates a carbocation, base attacks beta hydrogen of carbocation and creates double bond

Question 44

relationship between G, Ka, pKa, acidity

Answer 44

low G high Ka low pka high acidity (strong acid)

Question 45

chiral or achiral can rotate light

Answer 45

chiral

Question 46

levorotartory

Answer 46

rotate light counterclockwise (-)

Question 47

CARDIN-al

Answer 47

Charge Atom Resonance Delocalization INductive effects

Question 48

hydrogen acceptor

Answer 48

N, O, F with lone pair of electrons

Question 49

sn2 and stereochemistry

Answer 49

inversion of stereochemical configuration = wedge becomes dash/dash becomes wedge

Question 50

amine stretching

Answer 50

primary (1 R): 2 peak secondary (2 R): 1 peak tertiary (3 R): 0 peak

Question 51

advantages of pcl3/pbr3 over hcl/hbr

Answer 51

mild conditions no elimination products stereospecific = inversions no carbocations

Question 52

halogenation rate in basic condititions

Answer 52

halogen increase = rate increase

Question 53

amide stretching

Answer 53

primary (1 R): 2 peaks secondary (2 R): 1 peak

Question 54

strong base favors

Answer 54

E2

Question 55

know how to draw diazomethane and understand reaction page 16 chapter 10

Answer 55

know how to draw diazomethane and understand reaction

Question 56

Rate law of Sn1 and E1

Answer 56

only depend on reactant

Question 57

Zaitsev rule

Answer 57

major product of an elimination is the most stable one

Question 58

entropy

Answer 58

measure of randomness S<0 = less random S>0 = more random

Question 59

what makes a strong base

Answer 59

pka>14

Question 60

linear molecule with have higher/lower boiling point than T shaped molecule

Answer 60

higher

Question 61

Sn1 mechanism

Answer 61

leaving group leaves on its own creating a carbocation, nucleophile attacks carbocation

Question 62

what makes a strong acid

Answer 62

pka<0

Question 63

base strength increase as

Answer 63

stability of negative charge decreases

Question 64

rate determining step (RDS)

Answer 64

step with the highest transition state

Question 65

epoxides under basic, neutral, acidic conditions

Answer 65

basic = less hindered C neutral = less hindered C acid = most hindered C | review from notes

Question 66

deprotonating a carbon is only possible for an...

Answer 66

alkyne

Question 67

E1 and stereochemistry

Answer 67

not stereospecific molecule with less steric hinderance are favored