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Organic chemistry > final > Flashcards

final Flashcards

1
Q

formal charges

A

box method

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2
Q

relative contributions of resonance structures

A
  • smallest separation of oppositely charged atoms
  • negative charge on the most EN atom
  • minimize charges
  • complete octet
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3
Q

acid base reactions

A
  • equilibrium lies away from stronger acid
  • electrons flow from base to acidic H, and H leaves to form conjugate acid
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4
Q

lewis acid strength

A
  • lower pKa
  • larger atom connected
  • more EN atom connected
  • cationic
  • resonance
  • s character
  • nearby EN, inductive effect
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5
Q

lewis base strength

A
  • lower pKb
  • smaller
  • anionic
  • less resonance
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6
Q

boiling/melting point of alkanes

A

increases with molecular weight, less branching, and cyclic alkanes

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7
Q

IUPAC priority order

A
  1. alcohol
  2. alkenes
  3. alkynes
  4. halides/alkyl
    number rings to give all substituents lowest number
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8
Q

R-X

A

halide

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9
Q

R-OH

A

alcohol

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10
Q

R-O-R’

A

ether

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11
Q

R-SH

A

thoil

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12
Q

R-NH2

A

amine

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13
Q

R-S

A

sulfide

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14
Q

benzene as a functional group

A

arene

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15
Q

R-C(=O)-H

A

aldehyde

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16
Q

R-C(=O)-R

A

ketone

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17
Q

R-C(=O)-NH2

A

amide

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18
Q

R-C(=O)-OR

A

ester

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19
Q

R-C(=O)-OH

A

carboxylic acid

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20
Q

primary, secondary, tertiary carbons

A

only applies to alkanes, not multipe bonds

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21
Q

oxidation

A
  • increases oxidation state of carbon
  • increase C-O bonds
  • decrease C-H bonds
  • increase bonds more EN than C
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22
Q

torsional strain

A

from eclipsing interactions of neighboring groups

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23
Q

steric strain

A

groups that are separated by 3+ bonds interacting
Ex: 1,3-diaxial interactions

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24
Q

axial and equatorial substituents, chair flip

A
  • up C have up axial H and down equatorial H
  • down C have down axial H and up equatorial H
  • chair flip: axial becomes equatorial, but up stays up and down stays down
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25
Q

angle strain

A

when cycloalkane’s bond angles are forced to deviate from the ideal 109.5

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26
Q

cis and trans cycloalkanes

A

cis: both up or both down
trans: one up, one down

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27
Q

heteroaromatic rings

A

aromatic rings that include 1+ heteroatoms and pi bonds

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28
Q

chiral center

A
  • carbon with 4 different groups attached, not part of a multiple bond
  • ring path must be different in both directions
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29
Q

plane of symmetry

A

if present, molecule is achiral or mesocompound

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30
Q

enantiomer

A
  • mirror images are not superimposable
  • changing chirality at all the stereocenters
  • enantiomers have the same physical properties, except optical purity
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31
Q

diastereomer

A
  • changing chirality at some of the stereocenters
  • cis and trans are diastereomers
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32
Q

mesocompound

A
  • contain at least 2 chiral centers and a plane of symmetry
  • achiral compound with chirality centers
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33
Q

optical rotation

A

optically active: chiral, one enantiomer in excess
optically inactive: achiral

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34
Q

equivalent hydrogens

A
  • if there is a rotation axis or plane of symmetry that interchanges them
  • the two H on a terminal alkene are not equivalent because there is no rotation around a pi bond
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35
Q

number of signals in H NMR

A

number of nonequivalent H

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36
Q

integration

A
  • area under the peak
  • relative number of H in a particular environment
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37
Q

chemical shift of C or H

A
  • environment of C or H
  • adjacent EN and s character deshields and moves chemical shift left
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38
Q

splitting/multiplicity

A
  • how many neighboring H
  • # peaks - 1 = neighboring H
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39
Q

diastereotopic protons

A
  • if switch one H out, get diastereomers
  • attached to the same C, but are in different chemical environments
  • usually on a C next to a chiral C
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40
Q

number of signals in C NMR

A

number of non equivalent C

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41
Q

DEPT 45, 90, 135

A

45: C with H attached
90: CH
135: CH as negative

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42
Q

degree of unsaturation

A

1/2(2C + 2 + N - H - X)
- normal H: CnH2n+1
- O doesn’t matter
- N adds another H required
- X takes the place of an H

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43
Q

nitrogen in mass spec

A

molecular weight of a substance that contains C, H, O, and N is odd if the number of N is odd, VV

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44
Q

Br in mass spec

A

1:1

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45
Q

Cl in mass spec

A

3:1

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46
Q

benzene in mass spec

A

78g

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47
Q

carbocation

A
  • stability increases with substitution, especially with positive charge at benzylic position
  • sp2 planar, so nu can attack from either side
  • rearrangement by 1,2 alkyl or hydride shift, charge moves
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48
Q

Leaving group

A
  • can stabilize negative charge
  • EN, halides
  • larger
  • anion
  • resonance
  • SN1 and E1
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49
Q

nucleophile

A
  • anion
  • lone pair
  • less resonance
  • not EN
    Ex: CN-, N3-, RO-
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50
Q

electrophile

A
  • positive charge
  • resonance that makes positive charge
  • polarization away from C
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51
Q

strong nu, strong base

A
  • HO
  • CH3O-
  • EtO-
  • H2N-
  • E2 reactions
52
Q

strong nu, poor base

A
  • X-
  • nitrile
  • RS-
  • RSH-
53
Q

poor nu, strong base

A

tBuO-
E2 reaction

54
Q

poor nu, poor base

A
  • H2O
  • H3O+
  • EtNH2
  • CH3OH
  • E1 and SN1 reactions
55
Q

protic solvents

A
  • has a H that can leave
  • stabilizes nu and cationic intermediates and transition states
  • H2O
  • CH3OH/ethanol
  • NH3/ammonia
  • SN1, E1
56
Q

polar aprotic

A

DMSO, THF, acetone
SN2, E2

57
Q

SN1 and SN2 reactions of alcohols

A

requires initial protonation step to turn OH to H2O+, which is a good LG

58
Q

SN1: Alcohol + HX

A
  • inversion of stereochemistry because alcohol blocks, so nu does backside
  • faster and more favorable
    1. protonation
    2. LG leaves
    3. X- does backside attack
59
Q

SN2: Alcohol + HX

A
  • racemic mix
    1. protonation
    2. nu attacks electrophilic C, LG leaves
60
Q

SOCl2, pyridine

A

turns OH into Cl

61
Q

PX3

A

turns OH into Br or Cl

62
Q

TsCl, Pyridine

A

turns OH into OTs, great LG

63
Q

alcohol and H2SO4

A

elimination

64
Q

alcohol and POCl3

A

elimination

65
Q

SN1 mechanism

A
  1. LG leaves: rate determining
  2. nu attacks carbocation from either side
66
Q

SN2 mechanism

A
  1. nu backside attack, LG leaves
67
Q

E1 mechanism

A
  1. LG leaves
  2. base attacks beta H to form alkene
68
Q

E2 mechanism

A
  1. strong base attacks beta H to form alkene, LG leaves
69
Q

SN1 characteristics

A
  • 2, 3, resonance
  • weak nu, good LG
  • polar protic
  • two steps, carbocation
  • racemic mix
70
Q

SN2 characteristics

A
  • Me, 1
  • strong nu
  • polar aprotic
  • inversion of stereochemistry
  • one step, transition state
71
Q

E1 characteristics

A
  • 2,3
  • weak base, good LG
  • polar protic
  • mix, more sub alkene is major
  • two steps, carbocation
72
Q

E2 characteristics

A
  • 1 if bulky base, 2,3 if strong base
  • strong base/strong nu
  • polar aprotic
  • one product: more sub alkene (less sub alkene if bulky base)
  • one step, transition state
73
Q

what reaction mechanisms happen together

A

SN1 and E1

74
Q

activation energy

A

higher activation energy, higher hump, slower reaction rate, rate determining step

75
Q

energy diagram

A

max: transition state
local min: intermediate

76
Q

radical

A
  • species that contains an unpaired electron
  • single electron takes the place of an H
77
Q

radical stability

A
  • increases with substitution
  • most stable radical results from easiest C-H bond breaking
    vinylic, methyl, 1, 2, 3, allylic, benzylic
78
Q

bond dissociation energy (BDE)

A

increased radical stability, decrease BDE/bond strength

79
Q

homolytic bond cleavage

A

one bonding electron stays with each half of the molecule

80
Q

initiation

A
  • radical formation via homolytic bond cleavage of the weakest/lowest BDE bond
  • requires energy input: heat or hv
81
Q

propagation

A
  • non radical reacts with radical (atom abstraction) to form new radical and nonradical
  • radicals formed continue on
  • product usually formed
82
Q

termination

A
  • not included in reaction mechanism, non common or product forming
  • 2 radicals recombine to make a nonradical
83
Q

alkane + Cl2, hv

A
  • proceeds unselectively, forms mixtures based on radical stability
  • ratio depends on how many kind of each H and relative rate of forming each radical intermediate
  • put Cl on every C
84
Q

alkane + Br2, hv

A
  • proceeds selectively, one product forms
  • Br only adds to the more sub C
  • if equal sub, multiple products form
85
Q

alkene/alkyne + Br, ROOR/peroxides

A
  • Br on less sub C
86
Q

alkene + HX

A
  • alkane with X on more sub C
  • carbocation intermediate
  • mixture
  • markovnikov
87
Q

alkyne + HX

A
  • alkene with X on more sub C
  • markovnikov
  • trans/anti addition of H and X
88
Q

alkene + X2

A
  • alkane with trans X on each C
  • inversion at X- backside attack of halonium ion’s most sub C
89
Q

alkene + X2, H2O

A
  • alkane with OH on more sub C and X on less sub C
  • inversion at H2O backside attack of halonium ion’s most sub C
90
Q

alkyne + X2

A
  • 1 equiv: alkene with trans X on each C
  • 2 equiv: alkane with 2 X’s on each C
  • X- does backside attack of halonium ion’s most sub C
91
Q

alkene + BH3, NaOH, H2O2

A
  • alkane with OH on less sub C
  • syn addition of H and BH2
  • antimarkovinikov, BH2 on less sub C
  • replace BH2 with OH with retention of stereochemistry
92
Q

alkyne + BH3, NaOH, H2O2

A
  • carbonyl on less sub C
  • syn addition of H and BH2
  • antimarkovinikov, BH2 on less sub C
  • replace BH2 with OH
    enol tautomerizes to ketone or aldehyde
93
Q

alkene + H2, Pd/C

A
  • alkane with syn addition of H2 to less bulky face
94
Q

alkyne + H2, Pd/C

A

alkane

95
Q

alkyne + H2, Lindlar’s catalyst

A

cis alkene

96
Q

alkyne + H2, Na(s), NH3(l)

A

trans alkene
radical mechanism

97
Q

alkene + Hg(OAc)2, H2O, THF, NaBH4

A
  • alkane with OH on more sub C
  • mercurium ion intermediate
  • NaBH4 gets rid of HgOAc on less sub C
98
Q

alkyne + H2SO4, HgSO4, H2O

A
  • carbonyl on more sub C
  • enol tautomerization to ketone
99
Q

tautomerization

A
  • constitutional isomers that exist in equilibrium
  • enol (OH on =) is unstable
  • H2O attacks more sub C, so carbonyl ends up here
100
Q

acetylide anion

A
  • terminal alkynes are acidic
  • can be deprotonated by strong base (NaNH2) to form acetylide anion, which is a strong nu
  • acetylide anion can be used in SN2 reaction to form new C-C bond
101
Q

alkene + O3, Zn, H3O+

A

cleave double bond and add O

102
Q

alkyne + O3, H2O

A

cleave triple bond to double bond and add O, add OH to other bonds

103
Q

alkene + mCPBA

A

cis epoxide + carboxylic acid

104
Q

heat of hydrogenation

A

lower heat for more stable alkene

105
Q

allenes/cumulated dienes

A
  • structures that contain two adjacent double bonds
  • perpendicular pi bonds
  • chiral, but no chiral center
106
Q

substitution reactions of allylic halides

A
  • faster
    SN1: carbocation is resonance stabilized
    SN2: sterically more accessible to attack and delocalization lowers activation energy
107
Q

alkene + NBS, hv

A
  • allylic bromination
  • NBS releases Br radical
  • Br installs next to alkene
  • multiple products due to resonance
108
Q

alkene + Cl2, heat

A
  • allylic chlorination
  • Cl installs next to alkene
  • multiple products due to resonance
109
Q

diene

A

molecules that contain 2 alkenes

110
Q

conjugated dienes

A
  • two alkenes next to one another, resonance stabilized
  • S-trans configuration is more stable than S-cis
  • synthesized by elimination reaction of alkenes
111
Q

isolated diene

A

2 bonds between

112
Q

conjugated diene + HX and X2

A
  • low temp: 1,2 addition, terminal alkene, kinetic product forms before rearrangement
  • high temp: 1,4 addition, internal alkene, thermodynamic product forms after rearrangement
113
Q

diels alder reaction

A
  • cycloaddition of diene to alkenes to form two new C-C bonds
  • syn selectivity
  • requires s-cis conformation
  • trans alkene makes anti product, cis makes syn
114
Q

naming disubstituted aromatic compounds

A

ortho (o): 1,2
meta (m): 1,3
para (p): 1,4

115
Q

benzene with C(=O)-H

A

benzaldehyde

116
Q

benzyne with C(=O)-OH

A

benzoic acid

117
Q

benzene with alkene at benzylic position

A

styrene

118
Q

benzene with C(=O)-C

A

acetophenone

119
Q

benzene with OH

A

phenol

120
Q

benzene with OCH3

A

anisole

121
Q

benzene with NH2

A

aniline

122
Q

benzene with methyl

A

toluene

123
Q

substitution reactions of benzylic

A

faster because carbocation/transition state is more stable

124
Q

radical halogenation of benzylic

A
  • selectivity at benzylic position because breaking CH bond here gives us the most stable radical
  • rapid
125
Q

aromatic rules

A
  1. cyclic: each p orbital must overlap with p orbitals on 2 adjacent atoms
  2. planar: all p orbitals must be aligned so pi electron density can be delocalized. assume planar if ring size is over 7C
  3. completely conjugated: p orbital on every atom in the ring. p orbitals must be perpindicular
  4. satisfy huckel’s rule: 4n + 2 pi electrons where n is any integer
    - includes ions and heterocycles, but location/orbital of the lone pair on the heteroatom determines how many pi electrons there are for Huckel’s rule
126
Q

antiaromatic

A

cyclic, planar, conjugated, but has 4n pi electrons
less stable

127
Q

not aromatic

A

lack one of the 4
stability similar to acyclic analogs

Organic chemistry (6 decks)

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