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PHSC 204 > Exam 3 > Flashcards

Exam 3 Flashcards

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1
Q

for radical stability, look at

A

resonance
primary, secondary, or tertiary
sp3 hybridized or not

most stable: resonance
then tertiary, secondary, primary
least stable: radical on vinylic position

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2
Q

hydrohalogenation

A

addition of H-X across an alkene
* Markovnikov
* enantiomers

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3
Q

what to look for in hydrohalogenation

A

rearrangment

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4
Q

hydrohalogenation mechanism

A
  • alkene attacks H
  • bond between H and X goes to X
  • electron pair on X goes to carbocation
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5
Q

hydration

A

addition of OH and H across an alkene
* markovnikov
* racemic if chiral center
* makes rearranged and not rearranged products

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6
Q

hydration steps

A
  1. proton transfer
  2. nucleophilic
  3. proton transfer
    * same as hydrohalogenation except 1 more step to neutralize molecule
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7
Q

oxymercuration-demercuration

A

hydration w/ out rearrangment

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8
Q

reagent used for oxymercuration-demercuration

A
  1. Hg(OAc)2
  2. NaBH4
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9
Q

hydroboration-oxidation

A

hydration but anti-markovnikov

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10
Q

hydroboration-oxidation

A
  1. BH3*THF
  2. H2O2, NaOH
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11
Q

hydroboration-oxidation rule

A
  • either H and OH are both syn (both cis or both trans)
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12
Q

catalytic hydrogenation

A

hydrogenation: (addition of H and H across an alkene) - alkene to alkane
cataylic hydrogenation: hydrogenation with a catalyst
* syn (both trans or both cis)
* enantiomers
* if meso compound, then 1 product, no enantiomers

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13
Q

remember

A

enantiomer only form if there’s a chiral center

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14
Q

catalysts for catalytic hydryogenation

A

wilkinson’s catalyst

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15
Q

how to get 1 enantiomer

A

replace phosphine ligand on wilkinson’s catalyst with chiral ligand

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16
Q

halogenation

A

addition of X and X across an alkene

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17
Q

is halogenation anti or syn

A

anti

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18
Q

how are halohydrins formed

A

when halogenation happens in water
* addition of 1 halogen and 1 OH across an alkene
* halogen to less subsituted

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19
Q

dihydroxylation

A

addition of OH and OH across an alkene
* anti and syn

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20
Q

what do you need to make an alkyne

A

dihalide

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21
Q

geminal dihalides

A

2 halognes on the same C

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22
Q

vicinal dihalides

A

2 halogens on adjacent Cs

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23
Q

reaction to form alkyne

A

2 E2 rxns because there are 2 leaving groups
* 1st E2 forms an alkene
* 2nd E2 forms an alkyne
* mech: electrons on base to H, bond of H to C-C, loss of L.G
* requires strong base

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24
Q

catalytic hydrogenation of alkynes

A

alkyne to alkane
* in between, alkene forms (cis)

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25
for catalytic hydrogenation, how to stop reaction an alkene (not reach alkane)
poisoned catalyst ex. Lindlar's catalyst, Pd/BaSO4, Ch3OH
26
dissolving metal reaction
alkyne to trans alkene using sodium metal and ammonia
27
hydrohalogenation with ROOR alkynes
AM produces E and Z alkene
28
excess HX
1. same as normal HX to make an alkene 2. halohydrogenation from alkene to alkane
29
hydrogenation of alkynes w/ roor
e and z products retained
30
reactions that make enol - alkynes
acid catalyzed hydration and hydroboration oxidation
31
alkynes - acid catalyzed hydration
* hydration out make enol * enol has a constitutional isomer = keytone - arrow from pi bond to O
32
acid catalyzed hydration reagents
water with an acid ex. H2SO4
33
hydroboration-oxidation alkynes
1. alkyn to alkene 2. to keytone
34
what happens to alkynes when BH3 is used
2 successive addition rxns
35
how to prevent the second addition rxn?
use a diaxyl borane, not BH3
36
terminal alkene
* M yields a ketone * AM yields an aldehyde
37
what happens when an alkyne is treated with NH2
electrons on N go to H of alkyne bond of H and C to C ion formed SN2 rxn
38
alkylation
addition of an alkyl group to alkyne * leave everything the same * add #2 but not the halogen
39
alkylation reagents
1. NH2 2. RX
40
which alkyn reactions lead to the enol
* hydration * hydroboration
41
radical resonance mech
1. electron to middle of sigma bond 2. middle of pi bond to middle of sigma b ond 3. middle of pi bond to end of pi bond
42
is bromination or chlorination slower + more selcetive
bromintation
43
halogenation with radicals leads to what products
racemic
44
allylic bromination
Br atom to allylic position reagent: NBS
45
when to use bromination vs chrorination
* chlorination - one type of H * bromination - different types of H
46
alkyl halides rxn type
primary = sn2 tertiary = sn1 secondary=neither
47
naming alcohols
* replace e with ol * parent chain has OH * OH on lowest numbered C * write C # before parent name * cyclic alcohols, don't need to # alcohol C * include stereochemistry if chircal center
48
oxidation rxn
-H or +O
49
reduction rxn
+H or -O
50
reducing agents
1. H2 and catalyst 2. NaBH4 3. LiAlH4
51
what do reducing agents do
same structure but double bonded O becomes single bond OH
52
what is different about LiAlH4
strong enough to reduce esters and carboxylic acids
53
grignard reagent
same as reducing agent: double bonded O to single bonded OH & adds R of RMgX to the C w/ the OH 1. RMgX 2. H3O+
54
reagents to replace OH w/ Cl
SOCl2 py
55
reagents to replace OH w/ Br
PBr3
56
primary alcohol oxidation
1st oxidation = aldehyde * loses 2H: 1 from OH and 1 from alpha carbon 2nd oxidation = O added to OH
57
secondary alcohol oxidation
keytone formed * loses 2H: 1 from OH and 1 from alpha carbon
58
tertiary alcohol oxidation
no rxn
59
primary alcohols with chromic acid
carboxylic acid
60
chromic acid
CrO4H2
61
primary alcohols with PCC w/ CH2Cl2
aldehyde
62
secondary alcohols with PCC w/ CH2Cl2
keytone
63
swern oxidation
does same thing as PCC 1. DMSO, (CHCl)2 2. EtN
64
steps for alcohols being treated
1. find alcohols and label them as primary, secondary, tertiary 2. look at oxidizing agent 3. draw rxns based on alc. and agent off to the sode 4. draw backbone of og molecule 5. replace alcohols w/ new version
65
williamson ether synthesis reagents
1. NaH 2. RX
66
williamson ether mechanism
1. proton transfer (H to H) 2. SN2
67
alkoxymercuration-demercuration
addition of H and OH across an alkene (markovnikov)
68
epoxides
cyclic ethers
69
how are epoxides formed
treated with peroxy acids ex. MCPBA and peroxyacetic acid
70
epoxides are stereospecific, so
cis remains cis trans remainds trans
71
what do you need to open a ring
1. strong nuceleophile ex. NaOH, NaBr 2. H3O+
72
a ring opening rxn is similar to what
sn2 loss of a LG and nuc. attack except LG is leaving the carbon, not the molecule
73
which carbon gets attacked for ring opening
less subsituted one
74
ring opening vs acid catalyzed ring opening
ring opening: strong nuc. - sn2 (nuc attacks less subsituted C, loss of L.G) acid catalyzed ring opening: weak nuc. - protonation (electrons on O attack H), then SN2
75
if h2so4 is used as the nuc. for acid catalyzed ring opening, what is the nucleophile
CH3OH methanol
76
which carbon gets attacked for ring opening with acid
less subsituted one EXCEPT if there's a tertiary carbon, it attacks there
77
naming thiol
same thing but added thiol at the end
78
making a thiol
sn2 w/ NaSH
79
sulfide
ether but S instead of O
80
mass spectrum - peak height meanings
tall peak = more common = more stable short peak = less common = less stable
81
base peak
tallest peak and most stable
82
odd M+ peak
odd number of nitrogens, odd M.W
83
even M+ peak
even number of nitrogens, even M.W
84
M+1 peak
peak of itotop
85
chorine on mass spec
M = 3 M+2 = 1
86
bromine on mass specc
M=1 M+2=1
87
degree of unsaturation formula
88
radicals
1. split the X-X 2. draw hydrogen on the allylic position 3. draw arrow from middle of hydrogen bond to C, arrow from middle of H bond to air, arrow from halogen radical to air 4. attach radical * note product is H-X and radical on main thing, not radical on halogen

PHSC 204 (5 decks)

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