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42 Cards in this Set

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Which of the following can be extracted from an organic solvent with 6M of aqueous NaOH?

Benzoic Acid
Benzoin
1,4-dibromobenzene
Benzoic Acid
Which of the following can be extracted from an organic solvent with 6M of aqueous HCl?

Benzoic Acid
Benzoin
1,4-dibromobenzene
None of them can
Which is the most polar compound?

Benzoic Acid
Benzoin
1,4-dibromobenzene
Benzoic Acid
The best solvent for crystallizing a compound will be. . .
One in which the compound is least soluble @ lower temp and soluble @ higher temp
If there is an impurity present with your sample. . .
there will be a depression in the melting point
What is the role of iodine in the chemical reaction?
Solvent stabilizer
The product, benzopinacolone, form is a ___ rxn
B form
To calculate the yield of the product- what is the limiting reagent?
Benzopinacol
What is the oxidizing agent in the following rxn?

Borneol --NaOCl/Ch3COOH-->
Camphor --NaBH4--> Isoborneol
Sodium hypochlorite
In the reduxn of camphor by NaBH4, 2 diastereoisomers are obtained- with what product?
more exo product
Which spectroscopy will be more useful and quickest to infer oxidxn of borneol to camphor?
IR spectroscopy
Which spectroscopy will be more useful in determining the ratio of exo & endo product in rxn of camphor by NaBH4?
H NMR spectroscopy
In the reduxn experiment of camphor to isoborneol - NaBH4 is used over LiAlH4 because?
It is easier to handle
What conclusion can we draw from the stereochemistry of isoborneol?
Hydride is delivered to the endo face of camphor.
What do we measure in an infrared spectrum?
vibrational frequencies of chem bonds
What peak will disappear from the IR of camphor when it is reduced by NaBH4?
the peak at 2100-2200
In the Tollen's test for the aldehyde, the shinning on the test tube comes from the formation of what?
Silver metal
What's the electrophile bromination of anisole?
Br2
Why is anisole more reactive to electrophilic bromination than benzene?
The oxygen atom in anisole stabilizes the intermediate due to e- donation thru resonance.
Why does anisole undergo electrophilic substitution rather than addition when treated with Br?
the aromatic ring is very stable thus this stability is lost in an addition rxn.
What is the major product of dibromonation of anisole?
OCH3-Aromatic Ring-Br-Br
What's the active electrophile in the electrophilic nitration of methyl benzoate?
NO2+
Why is methyl benzoate less reactive to electrophilic nitration than benzene?
The ester group in methyl benzoate destabilizes the intermediate due to e- withdrawl thru resonance.
Why does the methyl benzoate undergo meta substitution rather than para when treated with bromine?
Meta groes through the most stable intermediate cation
Why does nitration of methyl benzoate give only monosubstitution and no di or tri-substitution?
the nitro group is strongly deactivation due to e- withdrawl thru resonance
What is the 1st step in base-catalyzed aldol condensation?
depronation of alpha carbon
What's the last step in base-catalyzed aldol condensation?
elimation of H2O
What intermediate elimates water in aldol condensation to give an alpha, beta-unsat.ketone?
Beta-hydroxy ketone
What's the 1st step in mech. of the rxn bw p-aminophenol and acetic anhydride to form acetaminophen?
Nucleophilic addition of p-aminophenol to acetic anhydride to form a tetrahedral intermediate.
What's the last step in mech. of the rxn bw p-aminophenol and acetic anhydride to form acetaminophen?
proton transfer from protonated amide to acetate anion
How does sodium hydrosulfite remove the colored impurities in the crude acetaminophen?
by a redox rxn
How will you purify your acetaminophen after you decolorize it
by recrystallization
what kind of substance is acetaminophen?
analgesic
In chlorosulfonation of acetanilide, why do we protect aniline?
aniline is more nucleophilic than the aromatic ring - so it will attack chlorosulfonic acid 1st;
aniline would be protonated by chlorosulfonic acid and turn to a meta directing group;
acetamido group is bulkier and favors P and O substitution
What is the 1st step in the mechanism of chlorosulfonation of acetanilide?
Electrophilicattack of chlorosulfonic acid para to the acetamido group acetanilide.
What is the 1st step in conversion of sulfonyl chloride to sulfonamide?
Nucelophilic attack of ammonia at the sulfonyl chloride
How do we remove the acetate protecting group from sulfanilamide?
by acid-catalyzed hydrolysis
What is a hazardous reagent?
chlorosulfonic acid
What type of rxn is the formation of methyl salicylate from salicylic acid and methanol?
esterification
What aton is protonated at the the first step in the mech.?
the carbonyl oxygen atom of the carboxylic acid
What is a hazardous agent?
sulfuric acid
What danger can occur from cracked glassware when performing a distillation at reduced pressure?
an explosion