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22 Cards in this Set
- Front
- Back
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BH3
-------> THF |
Hyrdoboration
Anti-markovnikov syn addition hydration -H and -OH added on the alkene Racemic mixture |
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(Li)NH3
---------------> |
produces a trans alkene from an alkyne
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Lindlar's Catalyst
--------------------> |
produces a cis alkene from an alkyne
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CH2I2
or CH2Cl2 |
produces a carbene
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NaNH2
----------> NH3 |
2* or 3* - dehydrohalogenation
1* only yeilds Alkylation of terminal alkynes builds carbon backbones removes H to form acetylide ion, add halogenated carbons, halogen leaves, carbons bond. |
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Zaitsev product
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elimination - the most substituted alkene produces the major product.
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group shifts
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methyl and hydride
when charging a 2* molecule, look in all directions for a shift to form a 3* |
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Markovnikov addition
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Hydrogens add to where there are already more hydrogens.
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Peroxides
(ROOR) |
produce antimarkovnikov
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OsO4
-------------> |
adds 2 -OH groups to a double bond. syn addition in a racemic form.
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KMnO4
---------------> heat |
Cleaves double bond
Unsubstituted carbons become CO2, monosubstituted carbons become carboxylates and disubstituted carbons become ketones |
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O3
---------------> |
Cleaves the double bond
Unsubstituted carbons are oxidized to formaldehyde, monosubstituted carbons are oxidized to aldehydes and disubstituted carbons are oxidized to ketones |
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Hydrogen Halides
(H-Br, H-I, H-X) ------------------> |
electrophilic addition to alkenes
Markovnikov addition to the double bond. Racemic reverse of an elimination reaction. |
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H2O(excess), H3O+
------------------------------> |
Acid catalyzed hydration of alkenes. Reverse reaction of dehydration of alcohols. First step adds H to double bond in zaitsev. Racemic. acid regenerated. *rearrangements*.
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Hg(OAc)2
----------------> THF |
Markovnikov alcohols from alkenes. rearrangements seldom occur. Non sterioselective. uses NaBH4 in second, unknown step.
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Br2
-----------> |
electrophillic addition of br2 or cl2 to alkenes. anti addition - cis in cyclic molecules.
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Br2
---------> H20 |
halohydrin formation.
before the second Br can attach itself to the alkene, H20 adds an -OH group. |
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SN1, SN2, E1, E2
general determinations |
consider:
leaving group 1*, 2*, 3* solvent heat |
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SN1
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always competes with E1
racemization from carbocation polar protic solvents 3*, or 2* w/ a weak nucleophile leaving group, nucleophile attacks, hydrogen leaves. |
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SN2
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aprotic polar (DMF, DMSO, HMPA)
1*, or 2* with a strong nucleophile. nucleophile backside attacks and "pushes off" the leaving group. |
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E2
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Classic dehydrohalogenation.
Base removes H, electrons swing to close C=C, kicks off leaving group. |
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E1
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competes w/ SN1 - when carbocation is formed, if the solvent can remove a H before substitution, forms an alkene via elim. bulky alkyl halides are good.
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