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29 Cards in this Set
- Front
- Back
List 13 different reactions that yield alcohols a product
(1 forms a diol) |
1. Hydrolysis of Alkyl Halides
2. Acid-Catalyzed Hydration of Alkenes 3. Hydroboration-Oxidation 4. Oxymercuration-Demurcuration 5. Reaction of Grignards (R--MgBr) with Aldehydes or Ketones 6. Reaction of Grignards (R--MgBr) with Esters 7. Reaction of Organolithiums (R--Li) with Aldehydes and Ketones 8. Reduction of Aldehydes and Ketones #1 9. Reduction of Carboxylic Acids 10. Reduction of Esters 11. Reaction of Grignards with Epoxides 12. Hydroxylation of Alkenes to form Diols 13. Reduction of Aldehydes and Ketones #2 |
|
REAGENTS FOR:
Hydrolysis of Alkyl Halides |
H2O, Ca(OH)2
-------------------------> |
|
REAGENTS FOR:
Acid-Catalyzed Hydration of Alkenes |
H3O+, H2O
------------------------> |
|
REAGENTS FOR:
Hydroboration-Oxidation |
1. B2H6, diglyme
----------------------------> 2. H2O2, HO- |
|
REAGENTS FOR:
Oxymercuration-Demurcuration |
1. Hg(OAc)2, THF, H2O
----------------------------> 2. NaBH4 |
|
REAGENTS FOR:
Reaction of Grignards (R--MgBr) with Aldehydes or Ketones |
1. diethyl ether
--------------------------> 2. H3O+ workup |
|
REAGENTS FOR:
Reaction of Grignards (R--MgBr) with Esters |
1. diethyl ether
--------------------------> 2. H3O+ workup |
|
REAGENTS FOR:
Reaction of Organolithiums (R--Li) with Aldehydes and Ketones |
1. diethyl ether
--------------------------> 2. H3O+ workup |
|
REAGENTS FOR:
Reduction of Aldehydes and Ketones #1 |
1. NaBH4 or LiAlH4
diethyl ether ----------------------------> 2. H2O |
|
REAGENTS FOR:
Reduction of Carboxylic Acids |
1. LiAlH4, diethyl ether
----------------------------> 2. H2O |
|
REAGENTS FOR:
Reduction of Esters |
1. LiAlH4, diethyl ether
----------------------------> 2. H2O |
|
REAGENTS FOR:
Reaction of Grignards with Epoxides |
1. diethyl ether
---------------------------> 2. H3O+ workup |
|
REAGENTS FOR:
Hydroxylation of Alkenes to form Diols |
(CH3)3COOH, OsO4 (cat)
----------------------------> tert-butyl alcohol, HO- |
|
PROPERTIES OF:
Hydrolysis of Alkyl Halides |
SN2 pathway
H2O used as nucleophile HO- can be used, but gives some elimination |
|
PROPERTIES OF:
Acid-Catalyzed Hydration of Alkenes |
'mark' addition
|
|
PROPERTIES OF:
Hydroboration-Oxidation |
'anti-mark' addition of OH to alkene
syn no rearrangement |
|
PROPERTIES OF:
Oxymercuration-Demurcuration |
'mark'
no stereoselectivity (only one isomeric product) - Overall transformation C=C to H-C-C-OH - Alternate method for hydrating alkenes to give alcohols |
|
PROPERTIES OF:
Reaction of Grignards (R--MgBr) with Aldehydes or Ketones |
1. forms 1*, 2*, and 3* alcohols
2. nucleophilic carbon of grignard attacks electrophilic carbon of carbonyl group. 3. workup with acid to protonate. |
|
PROPERTIES OF:
Reaction of Grignards (R--MgBr) with Esters |
1. standard grignard pathway that cycles through twice
2. molecule is cleaved at the ether oxygen before 2nd cycle |
|
PROPERTIES OF:
Reaction of Organolithiums (R--Li) with Aldehydes and Ketones |
Standard grignard pathway
2 Eq. of reagents required |
|
PRODUCTS OF:
Reduction of Aldehydes and Ketones #1 |
Aldehydes: 1* alcohols
Ketones: 2* alcohols |
|
PRODUCTS OF:
Reduction of Carboxylic Acids |
1* alcohols formed
|
|
PRODUCTS OF:
Reduction of Esters |
1* alcohols formed
|
|
POSSIBLE REAGENTS FOR:
Metal Reduction of Aldehydes and Ketones |
metal catalyst = Ni,Pd, Pt, or Ru
H2 |
|
PROPERTIES OF:
Reduction of Aldehydes and Ketones #2 |
syn addition
|
|
List:
- 3 reactions that form Thiols |
Thiols:
1. Substitution using an alkanethiolate (analogous to alkoxides) 2. Thiourea Reaction 3. Sulfide-Disulfide Reduction |
|
PROPERTIES/PRODUCTS OF:
Substitution using an alkanethiolate |
Sn2 of 1* and 2* alkyl chlorides
Inversion Product: thiol |
|
REAGENTS FOR:
Thiourea Reaction |
1. Thiourea (NH2)2CS
2. HO- 3. H3O+ |
|
REAGENTS/PROPERTIES FOR:
"Sulfide-Disulfide Redox Pair" - Di/sulfide Reduction - Thiol Oxidation |
Oxidation of a dithiol or 2 eq. of regular thiol:
- Product: Disulfide - Reagents: O2, FeCl Reduction of disulfide: - Product: Thiol - Reagent: (none listed) |