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Stereochemistry of Bromine Addition to trans-Cinnamic Acid

reaction separation purification analysis


1) To your 125 mL Erlenmeyer flask containing a stir bar,
add 10.0 mmol of trans-cinnamic acid and 6.0 mL of acetic acid. Collect the product by vacuum filtration and wash Purify the product by recrystallization Measure the melting point
2) Add 10 mL of a 1.0 M solution of bromine in acetic acid in the it on the filter with portions of ice-cold water until from 50% aqueous ethanol.
separatory funnel. the acetic odor is hardly noticeable.
3) Start the stirrer and add the bromine/acetic acid solution to the
Erlenmeyer flask in five or more portions waiting until the color
has faded to light orange before the addition of the next portion.
4) Allow the reaction mixture to stir 15 minutes at room temperature.
Chemical Safety

Bromine is highly toxic and corrosive, and its vapors can damage the eyes and respiratory tract. Wear gloves when
handling the bromine solution and dispense it under a hood; avoid contact and do not inhale its vapors.

Acetic acid causes chemical burns that can seriously damage skin and eyes; its vapors are highly irritating to the eyes
and respiratory tract. Wear gloves and dispense it under a hood; avoid contact and do not breath its vapors.

Cyclohexene is flammable; inhalation or skin absorption may be harmful. Avoid contact and do not breath its vapors.
Measure Melting Points

Unknown
Unknown + acetanilide
Unknown + phenacetin

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