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OChem 1 > Final > Flashcards

Final Flashcards

1
Q

chpt 1

HONC

A

Hydrogen 1
Oxygen 2
Nitrogen 3
Carbon 4

number of bonds to be neutral

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2
Q

chpt 1

What molecules perform hydrogen bonding?

A

NOF

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3
Q

chpt 1

Constructive interference

A

produces a bonding MO + larger wave amplitude

waves have effective overlap

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4
Q

chpt 1

Destructive interference

A

creates an anti bonding MO, or a node

waves do not have overlap

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5
Q

chpt 1

Orbitals are — in MO theory

A

conserved, the number you start with is the number you will end with

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6
Q

chpt 1

HOMO

A

highest energy occupied molecular orbital

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7
Q

chpt. 1

LUMO

A

lowest energy unoccupied molecular orbital

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8
Q

chpt 1

How many unhyridized p orbitals are there on an sp3 hybridized molecule?

A

0, 1 S orbital with 3 p orbitals

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9
Q

chpt 1

how many orbitals are formed in an sp2 hybridized molecule

A

3 orbitals

one unhybiridzed p orbital

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10
Q

chpt 1

what kind of orbitals overlap to form sigma bonds?

A

hybridized orbitals

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11
Q

chpt 1

what kind of bonds overlap to form pi bonds?

A

unhybridized

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12
Q

chpt 2

if a carbon has a - charge what is attatched to it?

A

three bonds and a lone pair

sp3 hybridized

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13
Q

chpt 2

if a carbon has a + charge what is attatched to it?

A

three bonds and no electrons

sp2 hybridized

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14
Q

chpt 2

localized electrons

A

e- that do not participate in resonance, if they cannot participate they are localized

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15
Q

chpt 2

delocalized electrons

A

e- that can participate in resonance

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16
Q

chpt 2

True or false? if you have a molecule that has lone pairs + a pi bond both will participate in resonance

A

false, the pi bond will participate, not the lone pairs

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17
Q

chpt. 2

How do you determine the most significant resonance structure?

A
  1. one with no charge will be the most significant
  2. if there are charges, the one with the fewest charges is most significant
  3. the structure with a negative charge on the most electronegative atom is most significant

stability = significance

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18
Q

chpt 3

Bronsted Lowry Acid

A

proton donor

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19
Q

chpt 3

Bronsted Lowry base

A

proton acceptor

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20
Q

chpt 3

acids will not lose a proton without a — present

A

base

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21
Q

chpt 3

explain the proton transfer mechanism

A

two arrows, one arrow from the atom to be protonated to the hydrogen and one arrow from the bond connecting the hydrogen to the connecting molecule

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22
Q

chpt 3

curved arrows start at places of — —

A

electron density

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23
Q

chpt 3

the — the pka value the stronger the acid

A

lower

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24
Q

chpt 3

strong acids create — bases

A

weak

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25
Q

chpt 3

CARIO

A

Charge
Atom
Resonance
Induction
Ortbials

weak is winner!

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26
Q

chpt 3

explain charge in CARIO

A

the neutral atom will be more stable than a charged atom

bases will likely be negative or neutral

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27
Q

chpt 3

Explain Atom in CARIO

A

a more electronegative atom with a charge will stabilize better

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28
Q

chpt 3

In the choice between S- and O- in CARIO which one would you choose?

A

you would choose S because if atoms are in the same colum the larger one is more stable

same row = electronegativity

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29
Q

chpt 3

explain resonace in CARIO

A

a charged atom stabilized by resonace will be more stable than one without resonance

delocalization stabilizes

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30
Q

chpt 3

Explain induction in CARIO

A

more electronegative atoms (like halogens) will stabilize a negative charge, the more electronegative atoms the better

the closer it is the better

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31
Q

chpt 3

explain Orbitals in CARIO

A

the more s character the better
sp>sp2>sp3

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32
Q

chpt 3

Which is the more stable base? NH2 or terminal alkyne?

A

this is an exception! a terminal alkyene is more stable than an amine

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33
Q

chpt 3

Lewis Acid

A

electron pair acceptor

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34
Q

chpt 3

Lewis base

A

electron pair donator

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35
Q

chpt. 4

Newman Projection

A

used to view a front and back carbon of a molecule

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36
Q

chpt. 4

staggard conformation

A

lower E, angles between groups are equal

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37
Q

chpt. 4

eclipsed conformation

A

high E, groups are close together likely creating strain

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38
Q

chpt. 4

Torsional strain

A

twisted, only occurs with ecplised conformations

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39
Q

chpt 4

steric strain

A

can occur in staggard and ecplised conformations where two groups that are not hydrogens interact

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40
Q

chpt 4

gauche conformation

A

staggard conformation with steric strain

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41
Q

chpt 4

what is the most stable conformation of cyclohexane?

A

chair conformation, no strain

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42
Q

chpt 4

every cyclohexane can have a max of – chair conformations

A

two

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43
Q

chpt. 4

True or false? after a ring flip the substiuents direction and position change

A

false, positon changes but not direction

if its up then its up if its down then its down

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44
Q

chpt 4

the most stable conformation will be one with all equitorial positions or ——

A

with the largest groups in equitorial positions

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45
Q

chpt. 5

Constiutional Isomers

A

same formula, different connectivity

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46
Q

chpt 5

stereoisomers

A

same formula, same connectivity, different spatial arrangments

different wedges and dashes

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47
Q

chpt 5

what does it mean to be chiral?

A

to be non superimposable on your mirror image

achrial= you can super impose

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48
Q

chpt 5

chiral center

A

a carbon with four different groups attatched

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49
Q

chpt 5

stereocenter

A

an atom where swapping two groups produces a stereoisomer of the atom

often sp2 atoms attatched to double bonds

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50
Q

chpt 5

enantiomer

A

the mirror image of a molecule

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51
Q

chpt 5

if you see a molecule that has been flipped across a mirrored surface and the wedges and dashes have also been flipped what is its relationship to the original molecule?

A

It is an identical molecule, if you do both options it creates an identical molecule

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52
Q

chpt 5

Steps to designating R and S

A

1, find the chiral center
2. assign priority 1-4 to the four groups
3. is the 1st group wedged forward? is the fourth group dashed back? If not you will count 1-3 and then switch your answer to the oppostie of what you got

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53
Q

chpt 5

what does it mean to optically active?

A

to be able to rotate a plane of polarized light

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54
Q

chpt 5

enantiomers will rotate light in equal but —–

A

opposite directions

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55
Q

chpt 5

how do you assign E and Z?

A
  1. assign priority to one of the two groups on either side of alkene
  2. if the higher priority groups are on the same side = Z
  3. if the higher priority groups are on the oppostie side = E
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56
Q
A
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57
Q

chpt 5

any compound with a plane of symmetry will be —

-or no chiral center

A

Achiral

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58
Q

chpt 5

How do you determine the number of stereoisomers in a molecule?

A

2^n where n= number of chiral centers
- subtract 1 if there is a plane of symmetry
- count two stereocenters on either side of a pi bond as 1
- draw out possible stereoisomers

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59
Q

chpt 6

enthalpy

A

the change in heat from reactants to products in a reaction

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60
Q

chpt 6

what is the favorable sign for H (enthalpy)?

A

a negative H sign = an exothermic reaction= favorable
a positive H sign= endothermic reaction = non favorable

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61
Q

chpt 6

entropy

A

the amount of disorder in a system

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62
Q

chpt 6

what is the favorable sign for entropy?

A

a positive entropy = favorbale
a negative entropy = non favorable

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63
Q

chpt 6

what sign of gibbs free energy indicates a spontaneous reaction?

A

a negative G indicates a spontaneous reaciton

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64
Q

chpt 6

exergonic

A

spontaneous, negative G, reactants are higher in E than products

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65
Q

chpt 6

endergonic

A

non spon, positive g, products are higher in E than reactants

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66
Q

chpt 6

Keq>1

A

products favored

67
Q

chpt 6

Keq < 1

A

reactants favored

68
Q

chpt 6

What are the four factors that affect the rate constant?

A
  1. temperature
  2. presence of a catalyst
  3. energy of activation
  4. steric orientation
69
Q

chpt 6

transition states

A

the peaks of energy diagrams, high energy and unstable, the number of them indicates the number of mechanistic steps

70
Q

chpt 6

intermediates

A

‘in’ the well, lower energy and more stable

71
Q

chpt 6

hammonds postulate

A
  • in an endergonic reation the transition states will more closely resemble products
  • in an exergonic reaction the transition states will more closely resemble the reactants
72
Q

chpt. 6

nucleophile

A

electron dense, often have a - charge or l.p.

ex: halides, negatively charged bases, HS-

73
Q

chpt 6

electrophile

A

electron deficent, attacked by nucleophiles

ex: carbocations, alkykl halide, carbonyl group

74
Q

chpt 9

alkyne

A

triple bond, one sigma two pi bonds, can react as nucleophiles in reactions

sp, 180, linear geometry

75
Q

chpt. 9

terminal alykne

A

end of a chain with an acidic H

76
Q

chpt 9

internal alkyne

A

sandwhiched between two carbons, within the chain

77
Q

chpt. 9

what sort of bases are strong enough to deprotonate a terminal alkyne?

A

C-, H-, N-

Not O-!

78
Q

true or false?

a reaction will react towards the weak acid weak base?

A

true! it moves away from the strong acid strong base

79
Q

chpt 7

substiutution reactions

A

loss of a leaving group + nucleophilic attack

will not react with tertiary alpha or beta carbons

80
Q

chpt 7

elimination reactions

A

loss of a leaving group + proton transfer to form an alkene

likely to react with a secondary or tertiary alpha carbon

81
Q

chpt 7

SN2 reaction

A

a bimolecular substiution (depends on the substrate and the nucleophile) reaction that favors unsubstitued substrate also concerted

only reaction that doesn’t want to be substitued

82
Q

chpt 7

Factors that affect nucleophilicity

A
  1. charge
  2. polarizability
  3. size
83
Q

chpt 7

How does charge affect nucleophilicity?

A

a charged nucleophile is a stronger one

84
Q

chpt 7

how does size affect a nucleophile?

A

a small nucleophile is a stronger one

ex: Br-, Cl-

85
Q

chpt 7

Polar protic solvent

A

Has hydrogen bonding, not favored for bimolecular reactions

favored for unimolecular reactions

86
Q

chpt 7

polar aprotic solvent

A

solvent without hydrogen bonding, not favored by unimolecular reactions

favored by bimolecular reactions

87
Q

chpt 7

Backside attack

A

During an SN2 reaction the nucleophile attacks opposite to the leaving group and inverts the carbon

88
Q

chpt 7

E2 reaction

A

bimolecular,loss of a leaving group + proton transfer to form an alkene

89
Q

chpt 7

are bimolecular reactions concerted or stepwise?

A

concerted

90
Q

chpt 7

what kind of base do you want for a E2 reaction?

A

strong base with a charge, no resonance and no induction

you want the loser of CARIO

91
Q

chpt 7

explain the characterisitics of a stable alkene

A
  • a trans alkene is more stable than a cis alkene
  • mono< di< tri< tetra substiuted
92
Q

chpt 7

Regiochemistry

A

where the reaction is taking place

zaitsev or hoffman? markovnikov? anti?

93
Q

chpt 7

Zatisev product

A

more substitued product

94
Q

chpt 7

Hoffman product

A

less substitued product

95
Q

chpt 7

examples of weak bases/ weak nucleophiles

A

H2O, MeOH, EtOH

96
Q

chpt 7

examples of strong nucleophiles (weak base)

A

Br-, Cl-, HS-

97
Q

chpt 7

Examples of strong base (weak nucleophile)

A

DBU, DBN, TBuOk

98
Q

chpt 7

examples of strong base strong nucleophile

A

MeO-, EtO-

99
Q

chpt 7

what position do the hydrogen and leaving group need to be in for E2 to happen

A

they need to be anti to each other, the leaving group also has to be axial if there is a ring

100
Q

chpt 7

Unimolecular reactions

SN1 and E1

A

stepwise reactions that are only dependent on the substrate

101
Q

chpt 7

True or false? Both unimolecular and bimolecular reactions can have rearrangments

A

False! bimolecular are concerted so no charges fully form

102
Q

chpt 7

Unimolecular reactions favor a — substrate

A

hinderd, heavily substitued

a tertiary substrate indicates unimolecular

103
Q

chpt. 7

a — reaction will produce both SN1 and E1 one will be — favored than the other

A

unimolecular, more

which is more favored depends on substrate

104
Q

chpt 5

Meso compound

A

two or more chiral centers and a plane of symmetry

rotate single bonds to check for ‘invisible symmetry’

105
Q

chpt 9

How are alkynes prepared?

A

By a double elimination reaction using excess base

106
Q

chpt 9

Does the first or second elimination in alkyne preparation require a strong base?

A

the second elimination requires a strong base to push the reaction to products

107
Q

chpt 9

Geminal Dihalide

A

both X are attatched to the same carbon

108
Q

chpt 9

vicinyl dihalide

A

the two X are attatched to adjacent carbons

109
Q

chpt 9

Why do we deprotonate to form the alkylide ion and then protonate it again?

A

to form more products/ push towards the products

110
Q

chpt 9

True or false? One equivalent of HX for hydrohalogenation of an alkyne can produce a geminal dihalide and an alkene with a X group?

A

false, it requires excess HX to form a geminal dihalide from an alkyne

111
Q

chpt 9

What alkyne reaction is teramolecular?

A

hydrohalogenation of alkynes

R= k[alkyne][HX]^2

112
Q

chpt 9

Which alkyne reaction can produce ketones and aldehydes?

A

hydration of alkynes
- Acid catalyzed= ketone
- boration= aldehyde

113
Q

chpt 9

Hydration of alkynes: Acid cataylized

A

markovnikov addition of OH +H across an alkyne using an acid and HgSO4 as a cataylst

creates an enol that converts into a ketone

114
Q

chpt 9

enol

A

an OH group is attatched to a C=C bond, it will likely be rapidly interconverting to another molecule

115
Q

chpt 9

tautomers

A

constiutuional isomers that interconvert between each other because of the migration of a proton

116
Q

chpt 9

Hydroboration Oxidation for alkynes

A

anti markovinikov addition of OH +H across an alkyne using a Boron molecule
- final product is an aldehyde

117
Q

chpt 9

Why is BH3 not often used for boration of alkynes?

A

Because a larger molecule is necesary to keep from adding to the enol twice

118
Q

chpt 9

alkylation of alkynes

A

addition of groups to an alkyne using a strong base to deprotonate a terminal alkyne

119
Q

chpt 9

If you want to do a double alkylation with acetylene what must you not do?

A

Add all the reagants in at once, this will not produce the products you want

120
Q

chpt 8

Additions reactions are favored at — temperatures

A

low

elimination is favored at high temp

121
Q

chpt 8

Hydrohalogenation: alkenes
- intermediate?
- rearrangment?
- regiochem?
- stereochem?
- reagants?

A
  1. carbocation intermediate
  2. yes can rearrange
  3. markovnikov addition
  4. if a chiral center is created R and S is observed
  5. HX
122
Q

chpt 8

Acid catalyzed hydration: alkenes
- intermediate?
- rearrangment?
- regiochem?
- stereochem?
- reagants?

A
  1. carbocation
  2. yes
  3. markovnikov addition
  4. same as hydrohalogenation, if chrial center is formed R and S is observed
  5. Dilute H2SO4 +H2O (concentrated favors reagants)
123
Q

chpt 8

Hydroboration oxidation: alkenes
- intermediate?
- rearrangement?
- regiochem?
- stereochem?
- reagants?

A
  1. boron intermediate
  2. no rearrangment
  3. antimarkovnikov
  4. syn addition
  5. BH3, THF
124
Q

chpt 8

Oxymercuration Demercuration: alkenes
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagants?

A
  1. cylic
  2. no
  3. markovnikov
  4. anti addition
  5. Hg(OAc)2
125
Q

chpt 8

Catalytic Hydrogenation: alkenes
- Intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagant?

A
  1. spaceship
  2. no
  3. N/A (adding same thing)
  4. syn addition
  5. H2 + metal catalyst
126
Q

chpt 8

halogenation: alkenes
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagant?

A
  1. cylic
  2. no
  3. N/A (Adding same thing)
  4. anti addition
  5. Cl2 or Br2
127
Q

chpt 8

Halohydrin: alkene
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagant?

A
  1. cylic
  2. no
  3. OH on more substitued position
  4. anti addition
  5. Cl2 or Br2 and H2O
128
Q

chpt 8

syn- Dihydroxylation: alkenes
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagant?

A
  1. concerted reaction
  2. no
  3. N/A
  4. syn addition
  5. Osmate ester or Postassium permangante (cold)
129
Q

chpt 8

Anti dihydroxylatin: alkenes
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagant?

A
  1. cylic epoxide
  2. no
  3. N/A
  4. anti addition
  5. Peroxy acids (MCPBA)
130
Q

chpt 8

Ozonolysis: alkenes
- intermediate?
- rearrange?
- regiochem?
- stereochem?
- reagants?

A
  1. N/A
  2. no
  3. N/A
  4. N/A
  5. O3
131
Q

chpt 8

Will concentrated or dilute acid favor the products?

A

a dilute acid will favor the products for an alkene addition reaction

132
Q

chpt 9

If the alkyne looks the same on both sides what kind of products can you expect?

A

A mix of products with the OH placed on either side of the alkyne

133
Q

chpt 9

Catalytic Hydrogenation: alkynes

A

using H2 + a metal cataylst or poisoned catalyst to get a alkane or the cis alkene

134
Q

chpt 9

What is lindlars catalyst?

A

a poisoned cataylst used to form the cis alkene from an alykne

135
Q

chpt 9

Dissolving metal reduction

A

Using Na + NH3 (l) to create the trans alkene from an alkyne

136
Q

chpt 9

Why is reduction of alkynes so synthetically useful?

A

Bc you can go from an alkyne to an alkene to a alkane

137
Q

chpr 9

What kind of product does excess X2 w/CCl4 and an alkyne yield?

A

A tetra halide alkane

no excess will yield a dihalide alkane

138
Q

chpt 9

What kind of product does an alkyne treated with 1 eq of X2 yield?

A

a tetrasubtitued alkene where the halogens are placed vicinally

anti and syn addition

139
Q

chpt 9

What kind of products will a terminal alkyne treated w/ O3 produce?

A

A carboxlyic acid + CO2

terminal carbon becomes CO2

140
Q

chpt 9

What kind of products will an internal alkyne treated with O3 produce?

A

Two carboxylic acids

141
Q

chpt 10

Radicals

A

species with one lone electron present, can be very reactive and unstable

142
Q

chpt 10

What kind of bond cleavage forms radicals?

A

homolytic bond clevage

143
Q

chpt 10

How would you describe the geometry of radicals?

A

A flatter trigonal pyramidal bc it is inbetween a carbanion and a carbocation

144
Q

chpt 10

True or false? Radicals and carbocations follow the same rearrangement rules.

A

False, radicals will not rearrange

145
Q

CHpt 10

homolytic BDE decreases with increasing —–

A

radical stability

146
Q

chpt 10

How many fish hook arrows for the most popular resonance pattern of radicals?

A

three arrows for a radical allylic to a pi bond

147
Q

chpt 10

Homolytic cleavage

A

intitation step, creates radicals by treatment of heat, light or peroxy acids (ROOR)

148
Q

chpt 10

Addition to a pi bond

radical reactions

A

formation of an alkane radical from an alkene, propogation step

opposite of elimination

149
Q

chpt 10

Hydrogen abstraction

A

removing hydrogen from its R group to form a carbon radical, propogation step

150
Q

chpt 10

Halogen abstraction

A

removal of X from X2 to form a radical group, propogation step

used in halogenation of an alkane

151
Q

chpt 10

Elimination

for radical reactions

A

X group is removed from molecule to form a double bond w/ contribution from the radical, propagation step

opposite of addition to a pi bond

152
Q

chpt 10

Couping

radical reactions

A

two radicals join together to form a bond, termination step

153
Q

chpt 10

Initiation

A

creation of radicals, start with none and end with some

154
Q

chpt 10

Propogation

A

movement of a radical around a molecule

155
Q

chpt 10

Termination

A

gets rid of radicals, start with some end with none

156
Q

chpt 10

what are the products and reagants of halogenation of an alkane?

A

reagnts: Br2 + light
products: alkyl halide + HX

enantiomers if chiral carbon is created

157
Q

chpt 10

what are the mechanistic steps of halogenation of an alkane?

A
  1. Homolytic clevage
  2. hydrogen abstraction to form carbon radical
  3. halogen abstraction to create alkyl halide
  4. coupling
158
Q

chpt 10

Halogenation occurs at the — substitued carbon for halogenation of an alkane

A

more substitued carbon, where more stable radical would be

159
Q

chpt 10

allylic bromination

A

the addition of bromine to an allylic positon on a compound by homolytic clevage of the weakest C-H bond

160
Q

chpt 10

regants and products of allylic bromination

A

reagants: an alkene + NBS and light
products: bromine on allylic postion with products from both radical resonance contributors

NBS reduces addition products

161
Q

chpt 10

Mechanism for allylic bromination

A
  1. initiation
  2. hydrogen abstraction from weakest C-H bond
  3. Halogen abstraction
  4. termination
162
Q

chpt 10

Hydrohalogenation of an alkene w/ peroxides (ROOR)

A

anti markovnikov addition of HBr across a pi bond

163
Q

chpt 10

reagants and products of antimarkovnikov additon of HBr

A

reagants: alkene+ HBr and ROOR
products: anti markovnikov addition of HBR

164
Q

chpt 10

Mechanism for hydrohalogenation of an alkene using HBr and ROOR

A
  1. initiaition, cleav O-O bond
  2. hydrogen abstraction
  3. addition of Br
  4. hydrogen abstraction of H to more sub. position
  5. termination

OChem 1 (8 decks)

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