17779632
Description
Flashcards by John Rivada, updated more than 1 year ago
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Created by John Rivada
about 5 years ago
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| Question | Answer |
| What are the three types of selectivity? | Regioselectivity: Which are of the molecule or which direction Stereoselectivity: How it will react (R vs S) Chemoselectivity: Which functional group(s) will react |
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| What is the reactivity scale towards nucleophiles? |
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| Oxidation vs. Reduction | Oxidation: decrease in # of H or increase in # of atoms that are more electronegative Reduction: increase in # of H or decrease in # of atoms that are more electronegative |
| What are the 4 classes of reducing agents? | 1. Group 13 hydrides 2. H2 + metal. cat. 3. 2H+ and 2e- (from metal) 4. Sn Hydrides |
| What are good reducing agents? | LAH DIBAL (diisobutylaluminum hydride) NaBH4 LiBH4 Borane something |
| Which is the harsher reducing agent of the two: NaBH4 or LiAlH4 | NaBH4 |
| Which of the following is the mildest and which is the strongest reducing agent: LiAlH4, DIBAL, LiBH4 | Strongest: LiAlH4 Mildest: LiBH4 |
| Using a reducing agent as the reagent, how can you make a 1° alcohol? | Aldehyde Ester Carboxylic Acid |
| Using a reducing agent as the reagent, how can you make a 2° alcohol? | Ketone |
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Ester is more reactive than carboxylic acid!!
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| Mechanism for Aldehyde/Ketone reduction? |
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| Mechanism for Ester reduction? | ** |
| Mechanism for Amide reduction? | ** |
| Using a reducing agent as the reagent, how can you make an amine? | Amide |
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| What should I use if I have a compound that has an eseter and a ketone and want to reduce both to alcohols? LiAlH4 or NaBH4? | LiAlH4 |
| What should I use if I have a compound that has an eseter and a ketone and want to reduce just the ketone? LiAlH4 or NaBH4? | NaBH4 |
| Slide 18 | ** |
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*Left aldehyde is supposed to be carboxylic acid
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*Left aldehyde is supposed to be carboxylic acid
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| What's so good about BH3 as a reducing agent? | It chemoselectivily reduces carboxylic acids over most things |
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second step is pH 5
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| Difference between NaBH3 and NaCNBh3 | CN on B make it a very week reducing agent NaCNBH3 is chemoselective for the reduction of IMINIUM ions |
| What is the difference between hydrogenation and hydrogenolysis? | Hydrogenation: addition of H2 across a double bond Hydrogenolysis: using H2 to break a single bond |
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| If your substrate is a benzyl amine or ether, what kind of metal should you use for hydrogenation? | Pd |
| If your substrate is an alkene, what kind of metal should you use for hydrogenation? | Pd Pt Ni |
| If your substrate is an aromatic ring what kind of metal should you use for hydrogenation? | Pt Rh Ni under high pressure |
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Fill in the reagents
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| Examples of Lindlar Catalysts | Pd, CaCO3, Pb(OAc)2 |
| Using a reducing agent as the reagent , how can I turn an imine into an amine? | NaCNBH3 and pH5 buffer H2 + cat. Pd/C |
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| What is the Rosenmund Reaction? | Acyl chloride to aldehyde Using H2, PD, and BaSO4 as support Doesn't reduce aromatic ring or carbonyl |
| Product of this reaction: Aromatic Ring - O - R + H2 , Pd/C | ROH Toluene |
| Product of this reaction: Aromatic Ring - CH2 - N-R2 + H2 , Pd/C | R2NH Toluene |
| Slide 26 | ** |
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| If you want to reduce a nitrile to an amine what should you use as a reagent? | LiAlH4, Bh3 Ra Ni (+H2), H2 + cat Pd/C Hydrogentation regaents (second list) tend to form 2° amine side products |
| If you want to reduce a nitrile to an aldeyde what should you use as a reagent? | DIBAL then acid dry HCl and SnCl2 then acid |
| Mechanism of thiocarbonyl formation? | Do we need to know this? |
| What is the Barton-McCombie Radical deoxygenation Reaction? |
Alcohols to Alkanes
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| What do you need to use to get an alcohol to an alkane? | The Barton-McCombie Radical deoxygenation Reaction |
| Slide 32 | ** |
| What do you need to use to get halide to an alkane? | The Barton-McCombie Radical deoxygenation Reaction |
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| What does the Mozingo reaction do? | Dithioacetal + Raney Nickel Ketone/Aldehyde to Alkane |
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Missing KOH in reagent
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Missing KOH in reagent
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And KOH as reagent
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Missing KOH as reagent
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| How can you go from carboxylic acid or acid chloride to alkane? |
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| Mechanism Slide 35 + 36 | ** |
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| Birch reduction mechanism | ** |
| EDG for birch reduction | Or, OH (becomes O-), NR2, alkyl |
| EWG for birch reduction | CO2H (as CO2-), amide |
| Incompatible groups for birch reduction | Ketone, aldehyde, nitro, acid chloride |
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| Reagents for Pinnick/Lindgren Oxidation |
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| Swern Ox | ** |
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**
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| Slide 55 Hydroboration | ** |
| Slide 56 | ** |
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