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64 Cards in this Set
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- 3rd side (hint)
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alkene + HX --> ?
regiochem? intermediate? stereochem? X=? |
alkyl halide (2º)
markov carbocation syn & anti I, Br, Cl |
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alkene + HBr/Peroxides
regiochem? intermediate? stereochem? |
1º alkyl halide
anti-markov radical syn & anti |
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alkene + H2O/H2SO4 --> ?
regiochem? intermediate? stereochem? alternatives to sulfuric acid? name? |
2º alcohol
markov carbocation syn & anti alcohols, H+ hydration, acid catalyzed |
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alkene + ROH/H2SO4 --> ?
regiochem? intermediate? stereochem? |
2º ether
markov carbocation syn & anti |
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alkene + ? --> 2º alcohol/ ether
step 1? step 2? |
1) Hg(OAc)2, H2O
>>use ROH to make ether 2)NaBH4 |
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alkene + Hg(OAc)2, H2O [or ROH] --> ?
regiochem? intermediate? stereochem? |
2º alcohol [ether]
markov--no rearrangements 3 membered ring (Hg(+)--OAc) is member anti |
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alkene + ? --> 1º alcohol
2 steps, 4 reagents |
1)BH3, THF
2)H2O2, OH(-) |
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alkene + BH3 --> ?
other reagents? regiochem? intermediate? stereochem? |
1º alcohol
BH3 w/ THF, then step 2:H2O2, OH(-) anti-markov--no rearrangements 4 membered ring (H--BH2--C--C) syn |
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alkene + X2 --> ?
possible additional reagents? regiochem? intermediate? stereochem? |
vicinal dihalide! (Rac)
Ch2Cl2, CCl4 ring-opening Nuc adds to more sub side 3-membered ring (C--C--Br+) anti (meso: trans AND anti) |
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alkene + X2/H2O --> ?
alternative to H2O? regiochem? intermediate? stereochem? |
halohydrin (1 OH, 1 X) (rac)
ROH ring-opening Nuc adds to more sub side 3-membered ring (C--C--Br+) anti |
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alkene + mCPBA --> ?
alternative to mCPBA? regiochem? stereochem? and then? |
epoxide (rac)
RCO3H ring-opening Nuc adds more sub if acidic, less if basic anti (meso: trans AND anti) and then-->H2O/H+[OH-]-->anti-diol (rac) |
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epoxide?
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3-membered ring, O is a member
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alkene + ? --> 2º alkyl halide
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HX
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alkene + ? --> 1º alkyl bromide
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HBr/peroxides or hv
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alkene + ? --> 2º alcohol
alternative solvents? |
H2O/H2SO4
alt: H2O, H+ |
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alkene + ? --> 2º ether
alternative solvents? |
ROH/H2SO4
alt: ROH, H+ |
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2-step way to:
alkene + ? --> 2º alcohol or ether intermediate? |
1) Hg(Oac)2, H2O
2) NaBH4 intermediate: 3m ring (C--C--Hg(+)) but Hg--OAc |
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alkene + ? --> 1º alcohol
intermediate? |
1) BH3, THF
2) H2O2, OH- intermediate: 4m pseudo-ring (C----C- - H - - BH2 - - ) |
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alkene + ? --> vicinal dihalide
intermediate? |
X2 (and maybe CH2Cl2 or CCl4)
intermediate: bromonium 3m ring |
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alkene + ? --> halohydrin
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X2/H2O [ROH]
intermediate: bromonium 3m ring |
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halohydrin?
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1 OH, 1 X vicinal
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alkene + ? --> epoxide
(2 choices) |
mCPBA
RCO3H |
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alkene + ? --> anti-diol
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mCBPA [RCO3H] --> epoxide
epoxide --> H2O + H+[OH-] |
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epoxide + ? --> anti-diol
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H2O + H+ [OH-]
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alkene + H2/cat --> ?
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alkane
meso possible: cis + syn |
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catalysts?
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Pd/C
Pd Pt Ni |
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alkane + ? --> alkane
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H2/Pt[Ni, Pd, etc]
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alkyne + H2/cat --> ?
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alkane
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alkyne + ? --> alkane
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H2/
Pd, Pt, Ni, etc |
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Lindlar's catalyst?
more like _______'s catalyst! |
SYN-dlars
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alkyne + H2/Lindlar --> ?
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CIS alkene (z)
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alkyne + ? --> cis (z) alkene
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LINDLAR and H2
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Alkyne + Na/NH3 (liq) --> ?
alternate metal? |
trans alkene (anti) (E)
lithium |
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alkyne + ? --> trans alkene (E)
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Na[Li]/NH3 (liq)
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alkene + KMnO4, OH(-) --> ?
KMnO4 is cold, dilute regio? |
vicinal diol (rac)
syn, meso: cis and syn |
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alkene + 1)OsO4, 2)H2O2 --> ?
alternative to H-perox? regio? |
vicinal diol (rac)
NaHSO3/H2O syn, meso: cis and syn |
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ozonolysis?
if step 2 is H2O2? |
cleaves pi-bond, creates aldehydes
creates COOH's |
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alkene + 1) O3, 2) Me2S --> ?
alternate reagent 2? alternate step 2 pathway? creates? |
2 aldehydes
Zn, H2O H2O2 --> COOH's |
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alkene + ? --> aldehydes
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1) Ozone
2) Zn H2O or DMS |
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alkene + ? --> carboxylic acids
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1) ozone
2) H2O2 |
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alkene + K2Cr2O7 conc --> ?
alternate reagent? |
carbox acids (cleavage)
KMnO4 + ∆ + OH(-) |
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K2Cr2O7 is the same as?
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Na2Cr2O7
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Na2Cr2O7 is the same as?
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K2Cr2O7
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alkene + KMnO4, OH(-), ∆ --> ?
step 2? |
carbox acids (cleavage)
2) H3O+ |
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alkene + ? --> carbox acids?
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K2Cr2O7
or? |
1) KMnO4, OH(-). ∆
2) H3O+ |
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cleave a pi bond!
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ozone + Me2S --> ?
ozone + H2O2 --> ? K2Cr2O7 --> ? KMnO4, ∆, OH(-) -->? |
aldehydes
carbox acids carbox acids carbox acids |
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terminal alkyne + HBr --> ?
regiochem? |
<bromoalkene> + HBr again --> ?
markov step 2 regiochem? |
geminal dihalide (both bromos on same C)
markov again |
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terminal alkyne + Br2 --> ?
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trans alkene + Br2 again --> ?
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tetrabromo (digeminal)
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terminal alkyne + ? --> geminal dihalide
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HBr (2eq)
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terminal alkyne + ? --> tetrahalo alkane
intermediate stereochem? |
Br2 (2eq)
trans |
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terminal alkyne + ? --> alkane
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H2/Pd
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terminal alkyne + H2/Pd --> ?
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alkane
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internal alkyne + H2/lindlar --> ?
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cis alkene
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internal alkyne + ? --> cis alkene?
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H2/lindlar
SYNLAR |
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internal alkyne + Na/NH3 (liq) --> ?
Na or? |
trans alkene
Li |
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internal alkyne + ? --> trans alkene?
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Na/NH3 (liq)
or lithium |
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terminal alkyne + Hg2+, H2O, H+
or [HgSO4, H2SO4] |
ketone
intermediate? |
enol
OH | R--CH=CH2 |
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terminal alkyne + 1) R2BH [Sia2BH], 2) NaOH, H2O2
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aldehyde
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enol
OH | R--CH=CH |
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internal alkyne + 1) ozone 2) H2O --> ?
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carboxylic acids
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internal alkyne + ? --> carboxylic acids
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ozone, then water
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internal alkyne + cold, dilute KMnO4, H2O --> ?
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vicinal diketone
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internal alkyne + ? --> diketone (neighboring Cs)
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KMnO4 (cold and dilute)
H2O |
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internal alkyne + 1)KMnO4, KOH, H2O 2) H2O, HCl --> ?
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carboxylic acids
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internal alkyne + ? --> carboxylic acids
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1)KMnO4, KOH, H2O
2) H2O, HCl |
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