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Lecture 11

CHEM 235 Lecture Notes - Lecture 11: Grignard Reaction, Phenylmagnesium Bromide, Separatory Funnel


Department
Chemistry
Course Code
CHEM 235
Professor
Dana Zendrowski
Lecture
11

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NOTES:
Grignard reaction: synthesis reaction involving an organometallic halide (yields
hydrogarbons and metal salts)
Grignard reagent = phenylmagnesium bromide
- Free radical reaction between bromobenzene and magnesium metal
- One of the most reactive reagent
- Act like an extremely strong base and as nucleophile
- Synthesized under anhydrous conditions
React Grignard reagent with benzophenone to form intermediate product (also under
anhydrous conditions).
Then add aqueous acid to intermediate to produce triphenylmethanol.
Byproduct of reaction: biphenyl
Remove biphenyl (highly soluble in petroleum ether) by washing crude with petroleum
ether, then recrystallize with ethanol.
EQUIPMENT:
drying tube (DRY) 125 mL Erlenmeyer flask
100 mL RB flask (DRY) 2350 mL separatory funnel
West condenser (DRY) + tubing filtering funnel
25 mL Erlenmeyer flask (DRY) Buchner funnel
2-400 mL beakers filtering flask + filtervac
10 mL graduated cylinder 100 mL beaker
25 mL graduated cylinder watchglass
spatula
CHEMICAL HAZARDS AND WASTE DISPOSAL
Magnesium
- HIGHLY FLAMMABLE. Inhalation of dust is irritating. Avoid direct viewing of burning
magnesium as eye injury may result
- Put in a “heavy-metal waste” container
Diethyl ether (anhydrous)
- HIGHLY FLAMMABLE. Keep away from open heat sources. May form explosive
peroxides. Harmful vapour.
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- Put in “liquid organic waste” container
Bromobenzene
- Irritating to skin
- Put in “liquid organic waste” container
Iodine
- Corrosive vapours. Avoid breathing vapour. Avoid contact with eyes and skin. Causes
burns.
- Put in “heavy-metal waste” container.
Benzophenone
- Use cautiously.
- Put in “solid waste” container
Sulfuric acid
- EXTREMELY CORROSIVE. CAUSES SEVERE BURNS. Prevent contact with skin and eyes.
- Dilute with plenty of water and wash down the sink
Sodium bicarbonate
- Use cautiously.
- Wash down sink with plenty of water.
Anhydrous sodium sulfate
- Use cautiously.
- Put in “solid waste” container
Petroleum ether
- HIGHLY FLAMMABLE.
- Put in “liquid organic waste” container
Ethanol
- FLAMMABLE. IRRITANT.
- Put in “liquid organic waste” container
Ethyl acetate
- FLAMMABLE. May ignite or explode with solid LiAlH4. Avoid vapours. Irritant to
mucous membranes, eyes and respiratory system.
- Put in “liquid organic waste” container.
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