CHM2211Lab

a. Why is the 5% sodium carbonate (aq) added to the organic layer?
(t-butyl chloride)
to neutralize the HCl
Why is Anhydrous magnesium sulfate is added to the organic layer?
(t-butyl chloride)
to dry the solution
What IR peak is missing from the cyclohexanone that originally was in the product?
(cyclohexanone)
the alcohol peak
What new peak shows up in the IR for cyclohexanone that wasn’t previously there?
(cyclohexanone)
carbonyl peak
How does the IR spectrum of the starting cyclohexanone change when product cyclohexanol forms?
(cyclohexanol)
The product will have an alcohol peak, the cyclohexanone does not.
What substance is extracted into the ether layer after the reaction is over?
(cyclohexanol)
cyclohexanol
What is the purpose of heating the dicyclopentadiene before addition of maleic anhydride?
(diels-alder)
convert it into useable cyclopentadienes
What happens to the cyclopentadiene if it is allowed to stand too long?
(diels-alder)
If left at room temperature the cyclopentadienes will dimerize into dicyclopentadiene (undesireable).
Why is sulfuric acid used?
(Methyl Nitrobenzoate)
to produce the electrophile needed for the reaction.
Why is the product washed with water?
(Methyl Nitrobenzoate)
to remove the acids
Why is the product washed with methanol?
(Methyl Nitrobenzoate)
We then washed the product with methanol to remove the more soluble ortho isomer.
Besides bromination at the para position, what small amount of other product might form when bromine reacts with acetanilide?
(Bromination of Acetanilide)
the isomer that forms besides the para is the ortho.
After the reaction, sodium bisulfite is added to react with what leftover substance?
(Bromination of Acetanilide)
Sodium bisulfite is added to the product to destroy any remaining unreacted BR₂
How will the IR spectrum of alcohol product differ from the ketone reactant?
(Grignard Reaction)
The product will have an alcohol peak at around 3300, which the reactant doesn’t
The glassware and reagents must be water free. With what substance will water react resulting in an unwanted side reaction?
(Grignard Reaction)
The Grignard reagents will react with H₂0, an unwanted side reaction.
What substance is extracted into the ether layer?
(Grignard Reaction)
The substance extracted into the ether layer is our product, 2-methyl-2-hexanol.
The diazonium salt is kept cold and used right away. What unwanted side reaction takes place with water?
(Azo dyes)
H₂0 and diazonium salt will react to produce a phenol, an unwanted product
Why is a solvent containing a solid product often cooled before filtering to obtain the solid product?
The solvent containing the product is often cooled before filtering so that all the product is allowed to crystalize and be caught on our filter.
After filtering with a Buchner funnel, why is the solid washed with a cold solvent?
The solid is washed with a cold solvent in order to further purify the solid and remove any clinging products that are not wanted.
When doing the Diels-Alder experiment, what was the purpose of cooling the receiving flask?
to prevent evaporation and dimerization.
What major peak is found in the reactant and product of the experiment in which we converted cyclohexanol to cyclohexanone? What two reagents were used to do this?
The major peak found on both the cyclohexanol and cyclohexanone is the sp3 peak which appears a little below 3000. The two reagents used for cyclohexanol to cyclohexanone were Na2Cr2O7 and H2SO4
How did we remove excess bromine in the bromination of acetanilide?
by using NaHSO3 aka sodium carbonate
In the azo dye methyl orange lab:

What color is the conjugate base?

dark red
In the azo dye methyl orange lab:

What color is the acid form?

bright orange
What does Glacial acetic acid mean?
“water free” (anhydrous) acetic acid
Alkyl Halide
R-X

X=F, Cl, Br, I

Amine
R’-N-R
|
H
Carboxylic acid
R-C-OH
||
O
ketone
O
||
R-C-R
Ether
/O/
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