17779632
Description
Flashcards by John Rivada, updated more than 1 year ago
|
Created by John Rivada
over 5 years ago
|
|
| 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 |
|
Image:
1b (binary/octet-stream)
|
Image:
1a (binary/octet-stream)
|
|
Image:
2b (binary/octet-stream)
|
Image:
2a (binary/octet-stream)
|
| What is the reactivity scale towards nucleophiles? |
Image:
3 (binary/octet-stream)
|
| 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 |
|
Image:
4b (binary/octet-stream)
|
Ester is more reactive than carboxylic acid!!
Image:
4a (binary/octet-stream)
|
| Mechanism for Aldehyde/Ketone reduction? |
Image:
5 (binary/octet-stream)
|
| Mechanism for Ester reduction? | ** |
| Mechanism for Amide reduction? | ** |
| Using a reducing agent as the reagent, how can you make an amine? | Amide |
|
Image:
6c (binary/octet-stream)
|
Image:
6a (binary/octet-stream)
|
|
Image:
6b (binary/octet-stream)
|
Image:
6a (binary/octet-stream)
|
| 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 | ** |
|
*Left aldehyde is supposed to be carboxylic acid
Image:
7b (binary/octet-stream)
|
*Left aldehyde is supposed to be carboxylic acid
Image:
7a (binary/octet-stream)
|
| What's so good about BH3 as a reducing agent? | It chemoselectivily reduces carboxylic acids over most things |
|
Image:
9b (binary/octet-stream)
|
second step is pH 5
Image:
9a (binary/octet-stream)
|
| 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 |
|
Image:
10b (binary/octet-stream)
|
Image:
10a (binary/octet-stream)
|
|
Image:
10c (binary/octet-stream)
|
Image:
10a (binary/octet-stream)
|
| 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 |
|
Fill in the reagents
Image:
11b (binary/octet-stream)
|
Image:
11a (binary/octet-stream)
|
|
Image:
11c (binary/octet-stream)
|
Image:
11a (binary/octet-stream)
|
| 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 |
|
Image:
12b (binary/octet-stream)
|
Image:
12a (binary/octet-stream)
|
|
Image:
12c (binary/octet-stream)
|
Image:
12a (binary/octet-stream)
|
| 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 | ** |
|
Image:
13b (binary/octet-stream)
|
Image:
13a (binary/octet-stream)
|
|
Image:
13c (binary/octet-stream)
|
Image:
13a (binary/octet-stream)
|
| 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
Image:
14 (binary/octet-stream)
|
| 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 |
|
Image:
15b (binary/octet-stream)
|
Image:
15a (binary/octet-stream)
|
|
Image:
15c (binary/octet-stream)
|
Image:
15a (binary/octet-stream)
|
| What does the Mozingo reaction do? | Dithioacetal + Raney Nickel Ketone/Aldehyde to Alkane |
|
Missing KOH in reagent
Image:
16b (binary/octet-stream)
|
Missing KOH in reagent
Image:
16a (binary/octet-stream)
|
|
Image:
16c (binary/octet-stream)
|
And KOH as reagent
Image:
16a (binary/octet-stream)
|
|
Missing KOH as reagent
Image:
16d (binary/octet-stream)
|
Missing KOH as reagent
Image:
16a (binary/octet-stream)
|
|
Image:
17b (binary/octet-stream)
|
Image:
17a (binary/octet-stream)
|
| How can you go from carboxylic acid or acid chloride to alkane? |
Image:
18a (binary/octet-stream)
|
|
Image:
18b (binary/octet-stream)
|
Image:
18a (binary/octet-stream)
|
|
Image:
18c (binary/octet-stream)
|
Image:
18a (binary/octet-stream)
|
| Mechanism Slide 35 + 36 | ** |
|
Image:
19b (binary/octet-stream)
|
Image:
19a (binary/octet-stream)
|
|
Image:
19c (binary/octet-stream)
|
Image:
19a (binary/octet-stream)
|
| 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 |
|
Image:
20b (binary/octet-stream)
|
Image:
20a (binary/octet-stream)
|
|
Image:
21b (binary/octet-stream)
|
Image:
21a (binary/octet-stream)
|
|
Image:
22b (binary/octet-stream)
|
Image:
22a (binary/octet-stream)
|
|
Image:
23b (binary/octet-stream)
|
Image:
23a (binary/octet-stream)
|
| Reagents for Pinnick/Lindgren Oxidation |
Image:
24a (binary/octet-stream)
|
| Swern Ox | ** |
|
Image:
25a (binary/octet-stream)
|
**
Image:
25b (binary/octet-stream)
|
|
Image:
26b (binary/octet-stream)
|
Image:
26a (binary/octet-stream)
|
|
Image:
27b (binary/octet-stream)
|
Image:
27a (binary/octet-stream)
|
|
Image:
28b (binary/octet-stream)
|
Image:
28a (binary/octet-stream)
|
|
Image:
28c (binary/octet-stream)
|
Image:
28a (binary/octet-stream)
|
|
Image:
29b (binary/octet-stream)
|
Image:
29a (binary/octet-stream)
|
|
Image:
30d (binary/octet-stream)
|
Image:
30a (binary/octet-stream)
|
|
Image:
30c (binary/octet-stream)
|
Image:
30a (binary/octet-stream)
|
|
Image:
30d (binary/octet-stream)
|
Image:
30a (binary/octet-stream)
|
|
Image:
31b (binary/octet-stream)
|
Image:
31a (binary/octet-stream)
|
|
Image:
31c (binary/octet-stream)
|
Image:
31a (binary/octet-stream)
|
|
Image:
31d (binary/octet-stream)
|
Image:
31a (binary/octet-stream)
|
|
Image:
32d (binary/octet-stream)
|
Image:
32a (binary/octet-stream)
|
|
Image:
32c (binary/octet-stream)
|
Image:
32a (binary/octet-stream)
|
|
Image:
32d (binary/octet-stream)
|
Image:
32a (binary/octet-stream)
|
|
Image:
33b (binary/octet-stream)
|
Image:
33a (binary/octet-stream)
|
|
Image:
33c (binary/octet-stream)
|
Image:
33a (binary/octet-stream)
|
|
Image:
33d (binary/octet-stream)
|
Image:
33a (binary/octet-stream)
|
|
Image:
34b (binary/octet-stream)
|
Image:
34a (binary/octet-stream)
|
|
Image:
34c (binary/octet-stream)
|
Image:
34a (binary/octet-stream)
|
| Slide 55 Hydroboration | ** |
| Slide 56 | ** |
Want to create your own Flashcards for free with GoConqr? Learn more.