|
Created by John Rivada
over 5 years ago
|
|
Question | Answer |
Image:
1b (binary/octet-stream)
|
Image:
1a (binary/octet-stream)
|
Image:
1c (binary/octet-stream)
|
Image:
1a (binary/octet-stream)
|
Mechanism!
Image:
1a (binary/octet-stream)
|
**missing an arrow from double bond to O
Image:
1d (binary/octet-stream)
|
What is the structure of an organometallic? | Can form dimers, tetramers, hexamers and can even involve solvent |
How do you make a Grignard reagent? |
Image:
2 (binary/octet-stream)
|
When making a Grignard reagent, what CAN R be?
Image:
2 (binary/octet-stream)
|
Alkyl, Aryl, Vinyl |
When making a Grignard reagent, what CAN NOT R be?
Image:
2 (binary/octet-stream)
|
Aldehyde Carbonyl Carboxylc Acid Acid Chloride Ester Nitrile Alcohol |
When making a Grignard reagent, what can the solvent be? | An ether of some sort: THF diethyl ether dimethoxyethane (DME) 1,4-dioxane |
What is the mechanism?
Image:
2 (binary/octet-stream)
|
Image:
3 (binary/octet-stream)
|
Why are 2 equivs of Li necessary?
Image:
4 (binary/octet-stream)
|
Li only has one e- in its valence shell |
What is Wurtz coupling? | Na or K pulls X and methyl groups bond |
Can you use organometallics with water? |
No!!! Pkb of H3C-Li is 48 and pka of H2O is 15.7 so full reaction
Image:
5 (binary/octet-stream)
|
What's great about an organometallic? | They can act as a base if no electrophilic site is present |
What is a a neo-pentyl position? | Next to a quaternary carbon |
What is Directed Ortho Metallation (DOM?) | When a heteroatom (O or N) complexes to the Li of the base and 'guides' the bas to the proton on the ortho carbon Occurs at RT or 0 C |
Mechanism for DOM? |
Image:
6 (binary/octet-stream)
|
Functional groups compatible with DOM? |
**first two structures are wrong!
alydehydes, ketones, and esters DO NOT work
Image:
7 (binary/octet-stream)
|
ROM | ** |
Why do you need 2 equivs of t-BuLi when reacting with t-BuX? | it likes to induce eliminations so 2 equivs are required |
Image:
8c (binary/octet-stream)
|
Image:
8a (binary/octet-stream)
|
Image:
8b (binary/octet-stream)
|
Image:
8a (binary/octet-stream)
|
Image:
9b (binary/octet-stream)
|
Image:
9a (binary/octet-stream)
|
Image:
9c (binary/octet-stream)
|
Image:
9a (binary/octet-stream)
|
Image:
10b (binary/octet-stream)
|
Image:
10a (binary/octet-stream)
|
Image:
10c (binary/octet-stream)
|
Image:
10a (binary/octet-stream)
|
Image:
11b (binary/octet-stream)
|
Image:
11a (binary/octet-stream)
|
Image:
11c (binary/octet-stream)
|
Image:
11a (binary/octet-stream)
|
Image:
12c (binary/octet-stream)
|
Image:
12a (binary/octet-stream)
|
Image:
12b (binary/octet-stream)
|
Image:
12a (binary/octet-stream)
|
What is the mechanism?
Image:
13a (binary/octet-stream)
|
Image:
13b (binary/octet-stream)
|
Image:
14c (binary/octet-stream)
|
Image:
14a (binary/octet-stream)
|
Image:
15b (binary/octet-stream)
|
Image:
15a (binary/octet-stream)
|
Image:
15c (binary/octet-stream)
|
Image:
15a (binary/octet-stream)
|
Image:
15d (binary/octet-stream)
|
Image:
15a (binary/octet-stream)
|
How do you make a 1° Alcohol using an organometallic? | Organometallic + dry formaldeyhde |
Image:
16b (binary/octet-stream)
|
Image:
16a (binary/octet-stream)
|
Image:
16c (binary/octet-stream)
|
Image:
16a (binary/octet-stream)
|
How do you make 2° and 3° alcohols using organometallics? | Add an organometallic to aldehyde or keytone |
Why does the top reaction not occur?
Image:
17a (binary/octet-stream)
|
Image:
17b (binary/octet-stream)
|
2 equivs of R2Li
Image:
18b (binary/octet-stream)
|
2 equivs of R2Li
Image:
18a (binary/octet-stream)
|
2 equivs of R2Li
Image:
18c (binary/octet-stream)
|
2 equivs of R2Li
Image:
18a (binary/octet-stream)
|
What is the mechanism?
2 equivs of R2Li
Image:
18a (binary/octet-stream)
|
Image:
18d (binary/octet-stream)
|
Slide 29 | ** |
Slide 30 | ** |
What is the best estimate for the mechanism for a Grignard Reaction? | ** |
What is the best estimate for he mechanism for allylic organometallics? | ** |
What is the Barbier Reaction? | Grignard Reagent using an allylic halide as Grignard precursor BUT Grignard formation and Grignard reaction are all in one pot |
Using organometallic reagents, what can you use as starting material to make carboxylic acids? | CO2 |
Using organometallic reagents, what can you use as starting material to make 1° alcohols? | DRY formaldehyde |
Using organometallic reagents, what can you use as starting material to make 2° and 3° alcohols? | Aldehyde for 2° Ketones for 3° |
Using organometallic reagents, what can you use as starting material to make ketones? | NOT esters Carboxylic acids Special Amides Nitriles |
Want to create your own Flashcards for free with GoConqr? Learn more.