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Ochem 2 > Final exam > Flashcards

Final exam Flashcards

1
Q

What does HONC tell you?

A

How many bonds those atoms want to be neutral
- 1,2,3,4

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2
Q

chpt 12

Why do alcohols have a high bp?

A

because of the hydrogen bonding

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3
Q

chpt 12

Alkoxides

A

conjugate bases of alcohols, RO- groups

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4
Q

chpt 12

What kind of bases are needed to deprotonate an alcohol?

A

C-, N-, H-

all very strong bases

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5
Q

chpt 12

CARIO

A

charge
atom
resonance
induction
orbital

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6
Q

chpt 12

when can you use substitution to form an alcohol?

A

only with a 1 or 3 substrated

2 would prompt elimination

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7
Q

chpt 12/chpt 8

what are the three ways an alcohol can be prepared via addition?

A
  1. acid cataylyzed (Dilute H2SO4)
  2. Hydroboration oxidation (BH3 THF)
  3. Oxymercuration demurcuration (Hg(AcO))
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8
Q

chpt 8

what is the intermediate for acid cataylyzed hydration of an alkene?

A

carbocation

be aware of rearrangements

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9
Q

chpt 8

Which one is markovnikov addition? Hydroboration or Oxymerucuration?

A

Oxymercuration

Hg(AcO)

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10
Q

chpt 12

Oxidation

A

increase in the number of C-e- atom bonds
decrease in the number of C-H bonds

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11
Q

chpt 12

reduction

A

increase in the number of C-H bonds
decrease in the number of C-e- atom bonds

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12
Q

chpt 12

What are the four reducing agents we know to change a ketone or aldehyde to a alcohol?

A
  1. LAH (strongest)
  2. NaBH4 (mild)
  3. H2 + metal catalyst
  4. grignard reagent
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13
Q

chpt 12

can LAH reduce carboxlyic acids and esters?

A

yes, it is strong enough. BH4 is not.

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14
Q

chpt 12

When do you need a protecting group with a grignard reagent?

A

When the group you are trying to react with contains an acidic proton

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15
Q

chpt 12

What are the reagents for adding a protecting group for a grignard reagent?

A

TMSCl +NE3+

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16
Q

chpt 12

What are the reagents for removing a protecting group for a grignard reagent?

A

TBAF

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17
Q

chpt 12

SOCl2 +PBr3 and a 1 or 2 alcohol =

A

a 1 or 2 alkyl halide

they just add the halogen to where the alcohol was

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18
Q

chpt 12

What are the two key oxidzing reagents we know?

A

PCC and Chromic acid

chromic acid stornger than PCC

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19
Q

chpt 13

Why are ethers often used as organic solvents?

A

bc they are not very reactive and have low bps

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20
Q

chpt 13

Williamson ether synthesis

A

makes an ether from an alcohol group
1. pt to create alkoxide
2. nuc attack on alkyl halide

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21
Q

chpt 13

Alkoxymercuration demurcuration

A

similar to oxymerucration but ads a RO group instead of an OH group

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22
Q

chpt 13

Acidic cleavage of ethers

A
  • heat + strong acid
  • converts an ether to two alkyl halides
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23
Q

chpt 13

What happens when a phenyl ether undergoes acidic cleavage?

A

one alkyl halide + one phenol

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24
Q

chpt 13

halohydrin +NaOH =

Br and OH must be anti to each other

A

creates an epoxide through an intermolecular reaction

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25
Q

chpt 13

what are the two ways to open epoxides?

A
  1. epoxide attacked by good nuc
  2. acid catalyzed ring opening
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26
Q

chpt 13

mechanism for opening of an epoxide using a good nucleophile

base catalyzed

A
  1. nuc attack
  2. proton transfer
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27
Q

chpt 13

mechanism for acid catalyzed opening of an epoxide?

A
  1. proton transfer
  2. nuc attack
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28
Q

chpt 13

if you have a primary and tertiary side of an epoxide which side will be attacked during acid catalyzed ring opeing?

A

the 3 side because of electronic effects

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29
Q

chpt 13

is sterochem conserved during acid catalyzed ring opening of an epoxide?

A

yes, conserved but inverted

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30
Q

chpt 13

how do you prepare a thiol?

A

alkyl halide + NaSH = thiol

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31
Q

chpt 13

How do you prepare a disulfide?

A
  1. Pt to make thiolate
  2. nuc attack by thiolate on halogen (Cl2, Brs)
  3. nuc attack by another thiolate
  4. pt for neutralization
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32
Q

chpt 13

disulfide

A

two sulfur atoms adjacent on a molecule

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33
Q

chpt 3

the — the pka value the weaker the acid

A

higher

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34
Q

chpt 3

equilibrium will move — from the strong acid/base

A

away

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35
Q

chtp 3

strong acid create — bases

A

weak

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36
Q

chpt 3

weak acids come from — bases

A

strong

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37
Q

chpt 3

Is a terminal alkyne or an amine more stable?

A

alkyne is more stable because of s character

CARIO exception

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38
Q

chpt 3

True or false? In a reaction with H2O and Cl- the reaction will favor the side the water

A

false, con bases of HCl are more stable than neutral water

cario exception

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39
Q

chpt 3

Lewis acid

A

electron pair acceptor

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40
Q

chpt 3

Lewis base

A

electron pair donor

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41
Q

chpt 4

What is a Newman projection

A

used to draw the conformation of a molecule from a specific pov, a front carbon and a back carbon

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42
Q

chpt 4

Staggard conformation

A

when the groups in a newman projection are equally spaced with no strain

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43
Q

chpt 4

eclipsed conformation

A

in a newman projection where the groups are close together, lots of strain

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44
Q

chpt 4

Torsional strain

A

torsional = twisted
strain that is only found in eclipsed conformations

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45
Q

chpt 4

Steric Strain

A

strain that can happen in eclipsed or staggard conformation, two groups that are not H are interacting

ex: an ethyl and a methyl interacting

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46
Q

chpt 4

Gauche conformation

A

staggard conformation that has steric strain

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47
Q

chpt 4

Why is the chair conformation the most stable/ strongest hexane conformation?

A

no ring strain, no torsional strain, no angle strain

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48
Q

chpt 4

True or false? every hexane can have only one chair conformation

A

false, every hexane can have two and only two chair conformations

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49
Q

chpt 4

What do you look for when considering what the most stable chair conformation is?

A
  1. are the largest substiuents equitorial?
  2. what are the interactions of the substituents?
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50
Q

chpt 4

Steroisomers

A

molecules that differ in their spatial arrangment of atoms

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51
Q

chpt 16

What is the difference between conjugated and cumulated dienes?

A

conjugated have a sigma bond separating the two double bonds
cumulated are pi bonds right next to each other

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52
Q

chpt 16

How do you prepare a diene?

A
  1. double elimination with two adjacent halogens and a strong bulky base
  2. single elimination with a pi bond and one adjacent halogen and a strong bulky base
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52
Q

chpt 16

Isolated dienes

A

pi bonds separated by 2 or more sigma carbon bonds

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52
Q

chpt 16

diene +HX =

A

pi bond + adjacent halogen

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53
Q

chpt 16

mechanism for addition of H + X to a diene

A
  1. pt to create resonance stabilized c+
  2. nuc attack by X- on both resonance structures
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54
Q

chpt 16

Thermodynamic product

A

the product favored at high temperatures, the most stable alkene

most stable usually = most substituted

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55
Q

chpt 16

kinetic product

A

product favored at low temperatures, most stable c+

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56
Q

chpt 16

is the diels alder reaction concerted or stepwise?

A

it is a peri cylic reaction so it is concerted

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57
Q

chpt 16

Is diels alder favored at high or low temperatures

A

at low temperatures the forward reaction is favored

reverse at high temps

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58
Q

cht 16

What makes a good diene for diels alder?

A

you need the diene to be cis for reaction so one locked into a ring will react faster

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59
Q

chpt 16

what makes a good dieneophile for diels alder?

A

dienophiles with ewg lower the activation energy to react faster

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60
Q

chpt 16

explain the endo and exo prefrence for diels alder products

A

endo: favored bc it is close to the pi bond of the product
exo: not favored

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61
Q

chpt 17

If you have a molecule with a chain that is longer that 6 carbons + a benzene ring what will you use for the parent name?

A

if the chain is longer than 6 carbons the chain will be the parent, not the ring

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62
Q

chpt 17

ortho

A

adjacent to each other, no carbons apart

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63
Q

chpt 17

meta

A

substituents that are one carbon apart

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64
Q

chpt 17

para

A

substituents that are two carbons apart

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65
Q

chpt 17

Why is benzene so stable?

A

because of its 6 overlapping p orbitals
- all bonding MOs filled

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66
Q

chpt 17

What does huckles rule state?

A

a ring must have an odd number of pi bonds to be aromatic

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67
Q

chpt 17

How do you draw a frost circle?

A
  1. draw a circle
  2. draw the molecule you are refrencing to with the pint down
  3. draw a line through each intersecting point in the shape to get all your bonding, anti bonding and non bonding MOs
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68
Q

chpt 17

toluene

A

benzene with a methyl

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69
Q

chpt 17

anisole

A

benzene with a methyl ether

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70
Q

chpt 17

styrene

A

benzene with an ethyl that has a 1-2 pi bond

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71
Q

chpt 17

Anti aromatic

A

if the molecule does not satisfy the 4n+1 rule, has an even number of pi bonds
- rings of 5 atoms or less

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72
Q

chpt 17

non aromatic

A

rings with 6 atoms or more than can change their shape to avoid antiaromaticity
- not fully conjugated
- follow huckles rule

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73
Q

chpt 17

positive charges on rings do what for orbtials?

A

it frees up a orbital and still participates in conjugation

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74
Q

chpt 17

negative charges do what for orbitals?

A

fills an orbital that participates in conjugation

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75
Q

chpt 17

Do localized electrons count towards huckles number of electrons?

A

No, bc they do not participate in resonance

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76
Q

chpt 17

Alkyl benzene + chromic acid

or KMnO4

A

benzoic acid
- benzoic position is completely oxidized to a carb acid

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77
Q

chpt 17

Can a benzylic carbon with no protons be oxidized?

A

No, there must be a benzylic proton present

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78
Q

chpt 17

alkyl benzene + NBS and heat

A

allylic/adjacent bromination, bromine added to benzylic position

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79
Q

chpt 17

Benzene ring + 3Eq H and lots of pressure

A

comletely reduced, all pi bonds removed

poof

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80
Q

chpt 18

EAS/ electrophilic aromatic substitution

A

one of the protons on the benzene is replaced with an electrophile

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81
Q

chpt 18

Does bezene act as a nucleophile or electrophile in EAS?

A

nucleophile

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82
Q

chpt 18

Mechanism for halogenation by EAS

A

1 nuc attack by benzene
(resonance structures)
2. pt to restore aromaticitiy

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83
Q

chpt 17

What does it mean when you say aromatic moiety is preserved?

A

the molecule starts aromatic and ends aromatic

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84
Q

chpt 5

constitutional isomers

A

same formula different connectivity

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85
Q

chpt 5

sterosiomers

A

same formula and connectivity but different spacial arrangements of atoms

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86
Q

chpt 5

chiral

A

to be non superimposable on your mirror image (can rotate polarized light)

eg: hands

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87
Q

chpt 5

achiral

A

superimposable over your mirror image

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88
Q

chpt 5

all chiral centers are stereocenters but —–

A

not all stereocenters are chiral centers

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89
Q

chpt 5

what hybridization of an atom often yields a stereocenter?

A

an sp2 atom attatched to a double bond is often a stereocenter

either both atoms of the double bond are or neither of them

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90
Q

chpt 5

enantiomers rotate light in equal but —

A

opposite directions

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91
Q

chpt 5

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

A

2^n rule
n= number of chiral centers
- plane of symmetry: subtract one from 2^n number
- count the 2 stereoisomers on either side of pi bond as 1

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92
Q

chpt 5

Meso compound

A

two or more chiral centers with a plane of symmetry

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93
Q

chpt 6

enthalpy

A

the exchange of energy between a system and its surroundings

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94
Q

chpt 6

entropy

A

the measure of disorder in a system

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95
Q

chpt 6

what favors a spontaneous reaction?

A

exothermic, negative enthalpy
increase in disorder, positive entropy (opposite sign of G)

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96
Q

chpt 6

What does endergonic mean?

A

that there is energy absorbed, reactants are lower in E than products

non favorabole

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97
Q

chpt 6

what does exergonic mean?

A

that energy was lost, reactants are higher in E than products

favorable

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98
Q

chpt 6

spontaneous does not mean —

A

fast, it can be slow and still be spontaneous

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99
Q

chpt 6

What kinds of things affect the rate of a reaction?

A
  1. activation energy of reaction
  2. temperature
  3. sterics of molecules that are reacting
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100
Q

chpt 6

by looking at a reaction coordinate diagram how can you tell how many transition and intermediate states there are?

A

transition states are the top of the hills
intermediates are ‘in the well’ they are the dips in the graph

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101
Q

chpt 6

The number of transition states tell you what?

A

how many mechanistic steps there are

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102
Q

chpt 6

hammonds postulate

A

in an exergonic reaction the reactants resemble the transition states
in an endergonic reaction the products resemble the transition states

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103
Q

chpt 6

What makes a good nucleophile?

A

small, and unhinderd with lots of electron density

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104
Q

chpt 6

What makes a good electrophile?

A

electron deficent, positve charge

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105
Q

chpt 18

What is the intermediate for EAS?

A

sigma complex

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106
Q

chpt 18

Reagants for Sulfonation by EAS?

A

SO3 +H2SO4= SO3H on a benzene ring

extra pt step

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107
Q

chpt 18

Nitration by EAS

A

benzene ring + HNO3 and H2SO4 = NO2 on a benzene ring

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108
Q

chpt 18

Friedel Crafts Alkylation

A

adding a alkyl group to a benzene ring
- alkyl halide + benzene ring and lewis acid

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109
Q

chpt 18

Why is a lewis acid so important for the friedel crafts alkylation?

A

the lewis acid makes the halide more electrophilic

110
Q

chpt 18

If the alkyl halide for friedel crafts is not 2 or 3 what happens?

A

there will likley be C+ rearrangments unless its a methyl group

halide must also be sp3 to react

111
Q

chpt 18

Friedel crafts acylation

A
  • adding a acyl (C=O) group to a benzene ring using an acid halide + Lewis acid + benzene ring
112
Q

chpt 18

True or false? Acylation will undergo polyacylation like how alkylation will undergo polyalkylation

A

False, acylation does not undergo poly reactions

113
Q

chpt 18

clemmensen reduction

A

A benzene ring with a C=O group attatched has the C=O group completely removed by HCl and Zn

114
Q

chpt 18

How do most activators direct?

A

ortho, para directors

115
Q

chpt 18

How do most deactivators direct?

A

para

not halogens tho

116
Q

chpt 18

Strong activators

A

lone pair that can only resonate within the ring

O minus, N minus groups

117
Q

chpt 18

Medium activators

A

lp that can resonate inside and outside the ring

esters, ethers

118
Q

chpt 18

weak activators

A

alkyl groups that donate via hyper conjugation not resonance

119
Q

chpt 18

Strong deactivators

A

NO2, CX3, any N+ atom

120
Q

chpt 18

Moderate deactivators

A

acyl groups with a double bond that is part of the congjuation of the ring

121
Q

chpt 18

weak deactivators

A

halogens that deactivate via induction, not resonance

ortho para directors

122
Q

chpt 18

Always follow the directing of the —- —-

A

strongest activator

123
Q

chpt 18

Examples of blocking groups

A

sulftonation is a popular blocking group because it can be easily removed by dilute H2SO4

124
Q

chpt 18

When can nitration NOT be performed?

A

when there is an amine or alcohol group already present

125
Q

chpt 18

How do you reduce nitrobenzene to aniline?

A

Fe/ Zn and HCl

126
Q

chpt 18

NAS, nucleophilic aromatic subtitution

A

the ring acts electrophilic in these reactions and is attacked by a nucleophile

127
Q

chpt 18

What are the three qualifications to undergo NAS?

A
  1. nitrogroup must be present
  2. LLG and nitrogroup must be ortho or para to each other
  3. LG must be a good LG
128
Q

chpt 18

Mechanism for NAS

A
  1. nuc attack
    (resonance pattern)
  2. LLG
129
Q

chpt 18

What is the intermediate for NAS?

A

meisenheimer complex

130
Q

chpt 18

Elimination addtion

A

this is used for addition to a ring when there is not a NO2 group present to perform NAS

131
Q

chpt 18

mechanism for elimination addition

A
  1. pt to create lp
  2. LLG
  3. nuc attack
  4. pt to restore aromaticitiy
132
Q

chpt 19

Why are aldehydes better electrophiles than ketones?

A

because they dont have two alkyl groups to stabilize and create steric hinderence

133
Q

chpt 19

Hydrate formation in acidic condtions

two OH on the same carbon

A

Ketone/aldehyde + H2O
- pt to create strong electrophile
- nuc attack
- pt for neutral product

134
Q

chpt 19

Hydrate formation under basic conditions

two OH attatches to same carbon

A

ketone/ aldehyde + NaOH
- nuc attack
- pt

135
Q

chpt 19

Acetal formation

two R-O groups on the same carbon

A

ketone/ aldehyde + excess R-OH group = acetal
- pt to create better electrophile
- nuc attack
- pt to create neutral intermediate
(hemiacetal is formed)
- pt to create good LG
- nuc attack
- LLG
- pt for neutral product

136
Q

chpt 19

How are acetals easily removed?

A

an acetal treated with water will be removed

makes good blocking group

137
Q

chpt 19

Imine formation

A

ketone/aldehyde treated with a primary amine

138
Q

chpt 19

Imine mechanism

A
  1. nuc attack by amine
  2. proton transfer
  3. proton transfer to create neutral intermediate
    (carbinol formed)
  4. proton transfer to create good LG
  5. LLG
  6. proton transfer to create neutral product
139
Q

chpt 19

Wolf Kishner reduction

A

imine treated with heat and a strong base reduces completley to an alkane

poof imine gone

140
Q

chpt 19

enamine formation

A

ketone/aldehyde + secondary amine

141
Q

chpt 19

Mechansim for enamine formation

A
  1. nuc attack
  2. proton transfer
  3. proton transfer for neutral intermediate
  4. pt for better LLG
  5. LLG
  6. pt to create adjacent double bond
142
Q

chpt 19

Cyanohydrin formation

CN +OH attatched to same carbon

A

HCN + ketone/aldehyde = cyanohydrin
- nuc attack
- pt

143
Q

chpt 19

Wittig reaction

A

ketone/aldehyde + witting reagent/ylide = alkene where C=O bond was

144
Q

chpt 19

is the witting reagent a carbon nucleophile or a phosphorus electrophile?

A

it is a carbon nucleophile

145
Q

chpt 19

Bayer Village oxidation

A

ketone + peroxy acid = ester formation

146
Q

chpt 19

for the bayer village reaction what is the order of prefrences?

A

H>3>2>ph>1>methyl

147
Q

chpt 20

True or false? carb acids are flat

A

True

148
Q

chpt 20

True or false? ewg destabilize acids, making them stronger

A

false, ewg stabilize acids making them weaker

149
Q

chpt 20

What are the four ways to make a carb acid?

not including hydrolysis of derivatives

A
  1. Ozonolysis of terminal alkynes
  2. oxidation of a primary alcohols with chromic acid or KnMO4
  3. oxidation of a benzlyic carbon with chromic acid
  4. CO2 + grignard reagent
150
Q

chpt 20

Mechanism for reduction of a carb acid to a alcohol using LAH/ BH3 THF

A
  1. pt to create carboxylate
  2. weird AlH2 and carb acid structure to create aldehyde (elimination)
  3. nuc attack by LAH
  4. pt to neutralize
151
Q

chpt 20

List the carb acid derivatives we know in order of most reactive to least

A
  1. acid halide
  2. acid anhydride
  3. ester
  4. amide
  5. nitrile
152
Q

chpt 20

nucleophilic acyl substitution

A

nuc attack on a carb acid to replace the OH group with something else

153
Q

chp 20

Where are the three places a pt will occur? for nucleophilic acyl subtituion

A
  1. before nuc attack if in acidic conditions
  2. between nuc attack and LLG for good LG
  3. After LLG if your nucleophile is neutral
154
Q

chpt 20

How can you prepare a acid halide?

A

carb acid (and other molecules) + SOCl2

155
Q

chpt 20

Hydrolysis (acid or base) of any carb acid derivative will yield?

A

a carb acid

156
Q

chpt 20

Alcoholysis of acid halides

A

acid halide + OH group = ester

157
Q

chpt 20

Aminolysis of acid halides

A

acid halide + amine = amide

158
Q

chpt 20

Reduction of acid halides

A

haldie + LAH and H3O = primary alcohol
acid halide +LiAl(OR)3 = stop reduction at aldehyde
acid halide + R2CuLi= stop reduction at ketone
acid halide + grignard = tertiary alcohol

159
Q

chpt 20

Preparation of acid anhydrides

A

acid halide + carboxylate = acid anhydride

160
Q

chpt 20

Four ways to prepare ester

A
  1. SN2
  2. Bayer Village reaction
  3. fischer esterification
  4. alcoholysis of acid halides
161
Q

chpt 20

Mechanism for saponification of esters

A
  1. nuc attck
  2. LLG
  3. pt
  4. pt to restore carb acid
162
Q

chpt 20

Mechanism for acid hydrolysis of esters

A
  1. pt
  2. nuc attack
  3. pt
  4. pt
  5. LLG
  6. pt

- same for esterification but with an OH group

163
Q

chpt 20

three ways to reduce esters

A
  1. ester + xs LAH = primary alcohol
  2. ester + grignard = tertiary alcohol
  3. ester + DIBAH = stops at the aldehyde
164
Q

chpt 20

amide + xs LAH =

A

amine

imine intermediate

165
Q

chpt 20

Two ways to prepare nitriles

A
  1. amide + SOCl2
  2. NaCN + alkyl halide
166
Q

chpt 20

Nitriles + grignard reagent

A

ketone

imine intermediate

167
Q

chpt 20

Nitriles + xs LAH =

A

amine

168
Q

chpt 21

which hydrogens are the most acidic on carbonyl containing compounds?

A

alpha hydrogens which are on the alpha carbons that are adjacent to the carbonyl containg carbon

169
Q

chpt 21

Enols

A

Overall neutral molecules that tautomerize with ketones

170
Q

chpt 21

stabilizing factors for enols

A
  1. an enol with conjugation
  2. an enol that is aromatic
  3. an enol that can form intermolecular hydrogen bonds
171
Q

chpt 21

enolates

A

over all negativley charged, often act as nucleophiles in reactions

172
Q

chpt 21

What are the two nucleophilic sites on a enolate and which one has the favored attack?

A

C and O nucleophilic sites, C- attack is favored

173
Q

chpt 21

What bases are used for irreversible enolate formation?

A

LDA and NaH

174
Q

chpt 21

Mechanism for acidic alpha halogenation

A
  1. pt
  2. enol formation
  3. nuc attack by enol pi bond on Br2
  4. pt for neutral product
175
Q

chpt 21

Does acid alpha bromination monobrominate or polybrominate?

A

it mono brominates at the more substitued position

176
Q

chpt 21

Does basic alpha halogenation monobrominate or polybrominate?

A

it will brominate until there are no longer alpha hydrogens at the least substitued postion

177
Q

chpt 21

What is the product of a ketone with three alpha hydrogen protons undergoing basic alpha halogenation?

A

a carboxylic acid

178
Q

chpt 21

Hell Volhard Zelinsky reaction

A

carb acid + PBr3 and Br2= Br at the alpha position of the carb acid

179
Q

chpt 21

Aldol addition reaction

A

aldehyde or ketone reacts with itself in basic conditions to form an aldehyde and alcohol group on one molecule

180
Q

chpt 21

Ways to keep crossed reactions from getting too messy

A
  1. have a reagent with no alpha protons
  2. treat with LDA or NaH to get irreversible enolate formation
181
Q

chpt 21

Aldol condensation

A

Aldol treated with a base and heat to get a pi bond and loss of the OH group in the form of water

182
Q

chpt 21

What is the driving force behind aldol condensation?

A

to create conjugated pi systems and improve stability through conjugation

183
Q

chpt 21

We know that aldol condesations are favored at most temperatures, at what temperatures are they not favored?

A

at very low temperatures (-10 C) may be low enough to not completley favor the aldol condensation

184
Q

chpt 21

What kind of rings are favored to form in diekmann and aldol intramolecualr reactions?

A

5, 6 membered rings

185
Q

chpt 21

Claisen condensation

A

Aldol condensation but with ethers which leaves a ketone and one ether

186
Q

chpt 21

What is necessary for the claisen condensation to happen?

A
  1. NO NaOH
  2. base must match ether R group
  3. at least 2 alpha protons present
187
Q

chpt 7

substitution reactions

A

nucleophilic attack + loss of a leaving group

188
Q

chpt 7

elimination reactions

A

forms a pi bond via pt and LLG

189
Q

chpt 7

True or false? SN2 prefers unhinderd, non sterically hindered substrates

A

true, SN2 is the only one that prefers nosteric hinderence

190
Q

chpt 7

SN2 and E2 are both — reactions

A

concerted reactions

191
Q

chpt 7

What makes a good nucleophile?

A
  1. charged = more e- density
  2. polarizibility aka how well they stabilize a charge
  3. size, smaller nucleophiles are stronger
192
Q

chpt 7

Polar protic solvent

A

has hydrogen bonding and creates a solvent shell around nucleophile
- only favored by unimolecular reactions

bad for bimolecular reactions

193
Q

chpt 7

Polar aprotic solvent

A

has no hydrogen bonding, does not create a solvent shell around nucleophile
- favorable by bimolecular reactions

194
Q

chpt 7

(for E2) the more highly substitued the base the more likely the product will be — substituted

A

less

195
Q

chpt 7

Zaitsev product

A

more substitued alkene

196
Q

chpt 7

Hoffman product

A

less substitued alkene

197
Q

chpt 7

What sterochemistry is necessary for elimination reactions?

A

the leaving group and proton need to be anti, if not the E2 reaction will not proceed

198
Q

chpt 7

what stereochemistry is necessary for E2 to happen on a ring?

A

the leaving group and proton must be anti AND leaving group has to be axial if not E2 will not happen

199
Q

chpt 7

How do unimolecular reactions differ from bimolecular

A

they are stepwise (rearrangements) and only rely on one thing (concentration of substrate) vs two things

200
Q

chpt 7

What promotes unimolecular reactions

A
  • polar protic base
  • 3 substrate with a weak base/ nucleophile
201
Q

chpt 7

sterospecific

A

only one stereoisomer is formed

202
Q

chpt 7

stereoselective

A

both stereoisomers are made but one is favored

203
Q

chpt 7

Regiospecific

A

only one product is formed, only one place on the molecule is reacted

204
Q

chpt 7

regioselective

A

two products are formed, two possible areas on the molecule to react

205
Q

chpt 7

Is the zaitsev or hoffman product favored by E1?

A

zaitsev always favored for E1

206
Q

chpt 7

Is zaitsev or hoffman favored by E2

A

with a bulky base hoffman is favored but other wise zaitsev is favored

207
Q

chpt 7

when turning an O into a better LG with TsCl is there inversion of the carbon?

A

no, bc its reacting with the O not the carbon

208
Q

chpt 8

Addition reactions

A

adding two groups to either side of a pi bond

209
Q

chpt 8

alkenes can act both as weak — and —

A

bases and nucleophiles

210
Q

chpt 8

Addditions are favored at — temperatures

A

low temps

elimination is favored by high temperatures

211
Q

chpt 8

Hydrohalogenation addition

A

H and X added across an alkene
- markovnikov reaction

212
Q

chpt 8

Acid catalyzed hydration of an alkene

A

add of H and OH across a pi bond
- H3O+ and an alkene

markovnikov addition

213
Q

chpt 8

Hydroboration Oxidation

A

BH3
- addition of OH and H across a pi bond

anti markovnikov

214
Q

chpt 8

Does hydroboration oxidation undergo syn or anti addition?

A

only syn addition

215
Q

chpt 8

Oxymercuration Demercuration

A

Hg(OAc2)
- addition of water across a pi bond

markovnikov addition

216
Q

chpt 8

Catalytic Hydrogenation

A

H2 and a metal catalyst to add H across a pi bond

217
Q

chpt 8

does catalytic hydrogenation have syn or anti addition?

A

syn addition bc of the intermediate (space ship, metal coordinates with alkene)

218
Q

chpt 8

Halogenation of alkenes

A

two halogens added across a pi bond using Cl2 or Br2

219
Q

chpt 8

does halogenation of an alkene do syn or anti addition

A

anti, bc of cylic intermediate

220
Q

chpt 8

why do cylic intermediates result in anti addition?

A

bc the ring takes up all the space on either the top or the bottom of the molecule

221
Q

chpt 8

Halohydrin addition

A

O-R + X across a pi bond

O added to more substituted position

222
Q

chpt 8

Does the halohydrin reaction do syn or anti addition?

A

anti bc of cyclic intermediate formed

223
Q

chpt 8

Dihydroxylation reaction

A

addition of two OH groups across an alkene
- can be anti or syn addition

224
Q

chpt 8

anti dihydroxylation

A

MCPBA/ Peroxy acids

225
Q

chpt 8

syn dihydroxylation

A

Osmate ester/ cold potassium permangenate

concerted process

226
Q

chpt 21

alkylation of the alpha position

A

alkyl halide + ketone/aldehyde = ketone/aldehyde with additional carbons

227
Q

chpt 21

mechanism for alkylation of the alpha position

A
  1. pt to form enolate
  2. nuc attack by enolate on alkyl halide`
228
Q

chpt 21

True or false? alkylation of the alpha position is an SN1 reaction

A

false, it is an SN2 reaction

229
Q

chpt 21

How do you form the kinetic product for alkylation of the alpha position

A

LDA and cold temps (-78 C)

230
Q

chpt 21

How do you form the thermodynamic product for alkylation of the alpha postion?

A

NaH at warm temperatures (25 C)

231
Q

chpt 21

Maloic ester synthesis

A

diethyl malonate treated with an akyl halide and then heated with acid yields a carb acid with additional carbons

232
Q

chpt 21

Mechanism for Malonic ester synthesis

A
  1. formation of the enolate
  2. nuc attack by enolate on alkyl halide
  3. hydrolyze esters into carb acids
  4. heat to yield CO2 and a carb acid with additional carbons
233
Q

chpt 21

Acetoacetic Ester Synthesis

A

ethyl acetoacetate + alkyl halide = ketone

234
Q

chpt 21

Mechanism for Aceotacetic ester synthesis

similar to Malnoic ester synthesis

A
  1. formation of enolate
  2. nuc attack by enolate on alkyl halide
  3. hydrolyze the one ester into carb acid
  4. heat to yield CO2 + ketone
235
Q

chpt 18

What are the issues with friedel crafts alkylation?

A
  1. if halide is not 2 or 3 rearrangments will occur which slow the reaction down
  2. polyalkylation is possible
  3. some rings are too deactivated to be added to
236
Q

chpt 21

Conjugated addition reactions

A

using the products of aldol condensation as electrophile bc of their 2 and 4 reaction positions to get alkylated ketones

237
Q

chpt 21

An attack at the 4 position is a — —

A

conjugated attack

238
Q

chpt 21

An attack at the 2 position is a — —

A

direct attack

239
Q

chpt 21

A strong nucleophile/ strong base used in conjugated addtion reactions gives what?

A

1’2 attack

kinetic product

240
Q

chpt 21

A weak nucleophile/base used in conjugated addition reactions gives what?

A

1’4 attack

thermodynamic product

241
Q

chpt 21

Mechansim for conjugate attack

A
  1. nuc attack by michael donor at 4 position
  2. pt to form enol
  3. tautomerization
242
Q

chpt 21

Michael reactions

A

michael donors attack michael acceptors to form alkylated ketones

243
Q

chpt 21

examples of michael donors

A

doubly stabilized enolates, R2CuLi, C- NO2 molecule

244
Q

chpt 21

Stork Enamine synthesis

A

converting a singly stabilized enolate into an enamine so it can act as a michael donor and perform conjugate addition reactions

245
Q

chpt 21

How do you alkylate at both the alpha and beta positions using conjugate addition?

A

In the second step, before you protonate to form an enol you can react the alpha position to get a second alkylation

246
Q

chpt 9

What kind of bases are strong enough to deprotonate an alkyne?

A

N-, C-, H-

NOT O-

247
Q

chpt 9

How do you prepare an alkyne?

A

double elimination using a geminal or vicinal dihalide
- 1st base can be anything
- 2nd base for 2nd elimination needs a strong base

248
Q

chpt 9

Mechansim for preparation of an alkyne

A
  • elimination 1 (pt and LLG)
  • elimination 2 (pt and LLG)
  • pt to creat alkynide ion (if alkyne is terminal)
249
Q

chpt 9

What is the purpose of the deprotonating step at the end of preparing an alkyne?

A

it yields the most product

250
Q

chpt 9

Hydrohalogenation of Alkynes

markovnikov

A

exs HX adds X to the more substitued position to get a dihalide

1 eq HX creates an alkene + 1 X at more sub positon

251
Q

chpt 9

Acid catalyzed Hydration of alkynes

markovnikov addition

A

forms ketones with H2SO4 and HgSO4 via enol and ketone tautomerization

252
Q

chpt 9

Hydroboration Oxidation of Alkynes

A

anti markovnikov addition of OH and H yields aldehydes

253
Q

chpt 9

Alkylation of Alkynes

A

Strong base used to deprotonate alkynes to react with 1 or methyl akyl halides

254
Q

chpt 9

Catalytic Hydrogenation of Alkynes

A

H2 + metal catalyst = alkane

255
Q

chpt 9

H2 + Lindlars catalyst and a alkyne =

Poisoned catalyst

A

cis alkene

256
Q

chpt 9

Na + NH3 (l) and an alkyne =

dissolving metal reduction

A

trans alkene

257
Q

chpt 9

terminal alkyne + O3 and H2O =

A

a carb acid + CO2

258
Q

chpt 22

Amines can act as bases, nucleophiles, and acids but never as —

A

eletrophiles

259
Q

chpt 22

Why are amines typically better bases than alcohols?

A

bc/ they are less electronegative so they don’t dissociate in water

260
Q

chpt 22

True or false? Amines are only deprotonted in neutral and basic conditions

A

false, they are only deprotonated in basic conditions

261
Q

chpt 22

What are the four old ways we know to make amines?

A
  1. reduction of NO2 on a benzene ring
  2. reduction of amide w/ xs LAH
  3. reduction of nitrile w/ xs LAH
  4. EA with NH2
262
Q

chpt 22

What are the three new ways we know to make amines

A
  1. Gabriel synthesis/ Potassium pthalimide
  2. Azide synthesis
  3. reduction amination
263
Q

chpt 22

Which of the three new ways can make 1, 2 and 3 amines?

A

reduction amination

264
Q

chpt 10

Heterolytic bond cleavage creates —

A

ions

265
Q

chpt 10

homolytic bond cleavage forms —

A

radicals

266
Q

chpt 10

stability of radicals

A

1< 2< 3< anything with resonance

resonance trumps all

267
Q

chpt 10

What is an Intiation step for radicals?

A

creates the radical

homolytic cleavage

268
Q

chpt 10

What is a propagation step for radicals?

A

electrons migrating around the the moleucle

addition, abstraction, elimination

269
Q

chpt 10

What is a termination step for radicals?

A

an ending step that gets rid of the radical

coupling

270
Q

chpt 10

halogenation of an alkane

A

Br2 + light = halogen at most stable position on alkane

271
Q

chpt 10

Allylic Bromination

A

NBS + heat = bromine on an allylic position

272
Q

chpt 10

Hydrohalogenation of an alkene

anti markovnikov

A

HBr + ROOR = anti markovnikov addition of H and Br

273
Q

chpt 10

True or false? Radicals do not rearrange?

A

True

unlike carbocations

274
Q

chpt 20

mechanism for fischer esterification

A
  1. pt
  2. nuc attack
  3. pt
  4. pt
  5. LLG
  6. pt
275
Q

chpt 20

reagents for a fischer esterification

A

carb acid + alcohol group and an acid catalyst

Ochem 2 (7 decks)

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