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Orgo Test 2 Flashcards

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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 “ze zame zide” 😂😂

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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
R and S configuration
R --> clockwise S--> counterclockwise | Tip: when driving a car if you turn the steering wheel clockwise you're going right (R)
26
Group Priority
1st priority goes to the atom/molecule with the highest atomic number
27
Priority for identical 1st atoms ex: CO and CH
CO has higher priority bc O has a higher atomic number than H
28
Priority for chains ex: CC and CCC
CCC has higher priority bc its a longer chain, this applies to all atoms except F
29
OH-R
alcohol
30
SH-R
thiol
31
NH2-R
amine
32
R-OR
ether
33
R-COO-R
ester
34
R-CtriplebondN
nitrile
35
enatinomer
non-identical, mirror image structures, not superimposable
36
stereoisomers
different orientations of atoms in space
37
Diastereomers
any stereoisomer that is not identical --> NOT MIRROR IMAGES
38
Mechanism of halogenations
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
meso
superimposable --> if they were laid on top of each other they would be identical
40
mechanism of hydrogenation
double bond breaks and the H attach bolded and with cis orientation --> the original substituents on the carbon double bond become dashed
41
hydride shift
a hydrogen on an adjacent more highly substituted carbon moves to the cationic (+) carbon (hydride shifts are preferred over alkyl shifts)
42
alkyl shift
if no hydrogens are on the adjacent carbon, an R group (like CH3) moves over to the positive carbon
43
after a hydride or alkyl shift remember the C without a full octet has a
positive charge
44
Naming alkynes
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
if there is an alkene and an alkyne the parent chain is named with the suffix
enyne
46
H2/Lindlar catalyst
reduces alkynes to cis alkenes
47
Na/NH3 reagents
reduces alkynes to trans-alkenes with Trans Hydrogens
48
H2/Pd(C) or H2/Pt catalysts
highly active catalysts and reduce alkynes to alkanes not stopping at alkenes
49
Adding water to alkynes
add water across the triple bond to form the unstable enol | perform tautomerization that converts the enol into the carbonyl form
50
tautomerization
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
enol
alcohol-substituted alkene --> unstable and rapidly rearrange through tautomerization
52
Markovnikov addition with oxymercuration reaction (no B)
OH adds to more substituted carbon
53
anti-Markovnikov addition with borane reaction
OH adds to less substituted carbon
54
creating alkynes
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
double dehydrohalogenation reactions
double-elimination reaction --> kicks off 2 halides and 2 H
56
Sn1
``` prefers tertiary and secondary (okay) Has NH or OH Poor nucleophile okay mix of stereoisomers rate = k[substrate] ```
57
Sn2
``` 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
secondary substrates
look for strength of nucleophile negatively charged nucleophiles and strong bases (OH) are for Sn2 poor nucleophiles --> sn1
59
E1
``` tertiary best secondary okay weak base okay has NH or OH bond no stereochemistry requirements rate=k[substrate] ```
60
E2
``` all substrates okay strong base needed all solvents okay antiperiplanar geometry required --> β -elimination rate=k[substrate][base] ```
61
E1 and E2 reactions form
alkenes --> a base abstracts a proton for the carbon adjacent to the leaving group
62
one step elimination reaction
E2
63
two step elimination reaction
E1
64
Naming alcohols
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
Alcohol reactivity
primary least --> tertiary most reactive
66
Boiling point increases in alkyls...
with larger groups ex: methyl has a lower boiling point than propyl
67
nucleophile
atom/ion with lone pairs used to form bonds --> lewis base --> anionic
68
N3
azide
69
OR
alkoxide
70
Rate of substitution with halides..
F is least reactant --> I is most reactant
71
Leaving group
group lost during nucleophile substitution or elimination --> usually halide
72
sn2 is
single step
73
sn1
multi step
74
inversion of configuration
nucleophile attacks from opposite of LG backside attack changes orientation
75
Sn2 substitution reactivity
``` tertiary is very slow --> methyl is fast most steric (most crowded) --> least crowded ```
76
Anion is most reactive in
neutral form (no charge)
77
nucleophilic trend across row
stronger base --> strong nucleophile
78
nucleophilic trend down group
larger atoms --> stronger nucleophile
79
Sn1 reactivity
methyl least reactive --> tertiary most reactive
80
x<12 carbons
cis
81
x>12 carbons
trans
82
stability of radicals
methyl least stable --> tertiary most stable
83
homolytic cleavage
bond breaking where each atoms retains a electron
84
F2
most reactive and exothermic
85
other halides
endothermic less reactive
86
LiALH4
reduces RCOOR (ester), RCOOH (carboxyl acids), RCOR (ketones) and RCHO (aldehydes)
87
R-CHO
aldehydes
88
R-CO-R
ketones
89
R-COOH
carboxyl acids
90
NaBH4
only reduces ketones and aldehydes
91
Grignard reagent
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
1) BH3, THF --> 2) H2O2
hydroboration, OH goes to least substituted carbon and the double bond is reduced
93
free radical
an uncharged molecule (typically highly reactive and short-lived) having an unpaired valence electron
94
formal charge
valence electrons - sticks -dots

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