17776833
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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Mechanism!
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**missing an arrow from double bond to O
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| What is the structure of an organometallic? | Can form dimers, tetramers, hexamers and can even involve solvent |
| How do you make a Grignard reagent? |
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When making a Grignard reagent, what CAN R be?
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Alkyl, Aryl, Vinyl |
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When making a Grignard reagent, what CAN NOT R be?
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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 |
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What is the mechanism?
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Why are 2 equivs of Li necessary?
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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
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| 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? |
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| Functional groups compatible with DOM? |
**first two structures are wrong!
alydehydes, ketones, and esters DO NOT work
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| 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 |
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What is the mechanism?
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| How do you make a 1° Alcohol using an organometallic? | Organometallic + dry formaldeyhde |
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| How do you make 2° and 3° alcohols using organometallics? | Add an organometallic to aldehyde or keytone |
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Why does the top reaction not occur?
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2 equivs of R2Li
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2 equivs of R2Li
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2 equivs of R2Li
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2 equivs of R2Li
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What is the mechanism?
2 equivs of R2Li
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| 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 |
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