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Orgo > Orgo Test 2 > Flashcards

Orgo Test 2 Flashcards

1
Q

2 Carbon Alkene

A

Ethene

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2
Q

3 Carbon Alkene

A

Propene

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3
Q

4 carbon alkene

A

Butene

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4
Q

When naming an Alkene how do you number the parent chain?

A

Start with the side that reaches the double bond first

BOTH PARTS OF THE DOUBLE BOND MUST BE INCLUDED IN THE CHAIN

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5
Q

Cis Stereochemistry

A

Identical substitute to stick of the same side

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6
Q

Trans stereochemistry

A

Identical substituents stick off opposite sides of the double bond

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7
Q

Z stereochemistry

A

High priority substituents are on the same side β€œze zame zide” πŸ˜‚πŸ˜‚

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8
Q

E stereochemistry

A

High priority substituents are on opposite sides of the double bond

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9
Q

Diene

A

Suffix used when an Alkene has 2 double bonds

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10
Q

Triene

A

Suffix when an Alkene has 3 double bonds

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11
Q

Protonation

A

Use electrons from the double bond to form a bond with the proton (H) in the hydrohalic acid

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12
Q

Carbocation

A

Positively charged carbon

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13
Q

Tertiary (3 degree) cation

A

3+ carbon substituents….most stable

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14
Q

Secondary (2 degree) cation

A

2 carbon substituents…..more stable than primary (1degree) cations

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15
Q

Primary (1 degree) cation

A

1 carbon substituent…least stable

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16
Q

Adding a hydrohalic acid to an Alkene involves…

A

Markovnikov addition

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17
Q

Markovnikov’s rule

A

The proton prefers to attach to the less substituted carbon

Doing this leaves the more substituted carbon with the positive charge

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18
Q

The most stable carbocation reacts…

A

Fastest

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19
Q

Halogenation

A

Addition of Br2 or Cl2

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20
Q

Hydrogenation

A

Addition of H2

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21
Q

Hydrogenation and cis products

A

occurs when alkene interacts with activated H atoms on the surface of a catalyst so the H atoms add to the same side of the double bond (called syn addition) resulting in cis product

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22
Q

Halogenation and trans products

A

two halides add to opposite sides of the double bond (anti addition)

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23
Q

halohydrin

A

one halide and one alcohol [OH]

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24
Q

dihalide

A

molecule with two halide groups

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25
Q

R and S configuration

A

R –> clockwise S–> counterclockwise

Tip: when driving a car if you turn the steering wheel clockwise you’re going right (R)

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26
Q

Group Priority

A

1st priority goes to the atom/molecule with the highest atomic number

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27
Q

Priority for identical 1st atoms ex: CO and CH

A

CO has higher priority bc O has a higher atomic number than H

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28
Q

Priority for chains ex: CC and CCC

A

CCC has higher priority bc its a longer chain, this applies to all atoms except F

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29
Q

OH-R

A

alcohol

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30
Q

SH-R

A

thiol

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31
Q

NH2-R

A

amine

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32
Q

R-OR

A

ether

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33
Q

R-COO-R

A

ester

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34
Q

R-CtriplebondN

A

nitrile

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35
Q

enatinomer

A

non-identical, mirror image structures, not superimposable

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36
Q

stereoisomers

A

different orientations of atoms in space

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37
Q

Diastereomers

A

any stereoisomer that is not identical –> NOT MIRROR IMAGES

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38
Q

Mechanism of halogenations

A

the double bond attacks a halide while the halide attacks the carbon (looks like a circle) the one halide is connected to both carbons from the broken double bond
the other halide then attacks the backside of the positively charged halide breaking one of the halide carbon bonds resulting in each carbon for the double bond being single bonded to a halide in trans stereochemistry

39
Q

meso

A

superimposable –> if they were laid on top of each other they would be identical

40
Q

mechanism of hydrogenation

A

double bond breaks and the H attach bolded and with cis orientation –> the original substituents on the carbon double bond become dashed

41
Q

hydride shift

A

a hydrogen on an adjacent more highly substituted carbon moves to the cationic (+) carbon (hydride shifts are preferred over alkyl shifts)

42
Q

alkyl shift

A

if no hydrogens are on the adjacent carbon, an R group (like CH3) moves over to the positive carbon

43
Q

after a hydride or alkyl shift remember the C without a full octet has a

A

positive charge

44
Q

Naming alkynes

A

the parent chain has the suffix yne and is numbered with the lowest possible number
substituents end with yl unless they’re halogens in which case o ex: bromo

45
Q

if there is an alkene and an alkyne the parent chain is named with the suffix

A

enyne

46
Q

H2/Lindlar catalyst

A

reduces alkynes to cis alkenes

47
Q

Na/NH3 reagents

A

reduces alkynes to trans-alkenes with Trans Hydrogens

48
Q

H2/Pd(C) or H2/Pt catalysts

A

highly active catalysts and reduce alkynes to alkanes not stopping at alkenes

49
Q

Adding water to alkynes

A

add water across the triple bond to form the unstable enol

perform tautomerization that converts the enol into the carbonyl form

50
Q

tautomerization

A

proton transfer and double bond shift take place

the proton on oxygen transfers to the adjacent carbon while the double bond changes from C=C to C=O

51
Q

enol

A

alcohol-substituted alkene –> unstable and rapidly rearrange through tautomerization

52
Q

Markovnikov addition with oxymercuration reaction (no B)

A

OH adds to more substituted carbon

53
Q

anti-Markovnikov addition with borane reaction

A

OH adds to less substituted carbon

54
Q

creating alkynes

A

reactions require terminal alkyne and a very strong base (usually 2NaNH2 or 2NaOH)
the halides get kicked off and a triple bond is formed, if there is already a triple bond and youre using only a strong acid add an ethyl to the triple bond if there is a strong acid and a solvent add whatever CH(n) in the 2nd solvent to the triple bond
ex: NaNH2 and CH3Br add CH3 to the triple bond

55
Q

double dehydrohalogenation reactions

A

double-elimination reaction –> kicks off 2 halides and 2 H

56
Q

Sn1

A 
prefers tertiary and secondary (okay)
Has NH or OH
Poor nucleophile okay
mix of stereoisomers
rate = k[substrate]
57
Q

Sn2

A 
prefers methyl and primary substrates
prefers less steric crowding 
no NH or OH bonds
good nucleophile needed
product has inverted stereochemistry
rate = k[substrate][nucleophile]
58
Q

secondary substrates

A

look for strength of nucleophile
negatively charged nucleophiles and strong bases (OH) are for Sn2
poor nucleophiles –> sn1

59
Q

E1

A 
tertiary best secondary okay
weak base okay
has NH or OH bond
no stereochemistry requirements
rate=k[substrate]
60
Q

E2

A 
all substrates okay
strong base needed
all solvents okay
antiperiplanar geometry required --> Ξ² -elimination
rate=k[substrate][base]
61
Q

E1 and E2 reactions form

A

alkenes –> a base abstracts a proton for the carbon adjacent to the leaving group

62
Q

one step elimination reaction

A

E2

63
Q

two step elimination reaction

A

E1

64
Q

Naming alcohols

A

begin with normal naming rules, but number with the side that reaches OH first
parent chain ends in anol
assign stereo chemistry –> if a chiral center is shown number this before the substituents

65
Q

Alcohol reactivity

A

primary least –> tertiary most reactive

66
Q

Boiling point increases in alkyls…

A

with larger groups ex: methyl has a lower boiling point than propyl

67
Q

nucleophile

A

atom/ion with lone pairs used to form bonds –> lewis base –> anionic

68
Q

N3

A

azide

69
Q

OR

A

alkoxide

70
Q

Rate of substitution with halides..

A

F is least reactant –> I is most reactant

71
Q

Leaving group

A

group lost during nucleophile substitution or elimination –> usually halide

72
Q

sn2 is

A

single step

73
Q

sn1

A

multi step

74
Q

inversion of configuration

A

nucleophile attacks from opposite of LG
backside attack
changes orientation

75
Q

Sn2 substitution reactivity

A 
tertiary is very slow --> methyl is fast
most steric (most crowded) --> least crowded
76
Q

Anion is most reactive in

A

neutral form (no charge)

77
Q

nucleophilic trend across row

A

stronger base –> strong nucleophile

78
Q

nucleophilic trend down group

A

larger atoms –> stronger nucleophile

79
Q

Sn1 reactivity

A

methyl least reactive –> tertiary most reactive

80
Q

x<12 carbons

A

cis

81
Q

x>12 carbons

A

trans

82
Q

stability of radicals

A

methyl least stable –> tertiary most stable

83
Q

homolytic cleavage

A

bond breaking where each atoms retains a electron

84
Q

F2

A

most reactive and exothermic

85
Q

other halides

A

endothermic less reactive

86
Q

LiALH4

A

reduces RCOOR (ester), RCOOH (carboxyl acids), RCOR (ketones) and RCHO (aldehydes)

87
Q

R-CHO

A

aldehydes

88
Q

R-CO-R

A

ketones

89
Q

R-COOH

A

carboxyl acids

90
Q

NaBH4

A

only reduces ketones and aldehydes

91
Q

Grignard reagent

A

MgBr –> add to carbonyl (C=O) compounds,acts like an anion and attaches the C chain to the C=O and reduces the double bond while adding OH

92
Q

1) BH3, THF –> 2) H2O2

A

hydroboration, OH goes to least substituted carbon and the double bond is reduced

93
Q

free radical

A

an uncharged molecule (typically highly reactive and short-lived) having an unpaired valence electron

94
Q

formal charge

A

valence electrons - sticks -dots

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