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42 Cards in this Set
- Front
- Back
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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
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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
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Which is the most polar compound?
Benzoic Acid Benzoin 1,4-dibromobenzene |
Benzoic Acid
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The best solvent for crystallizing a compound will be. . .
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One in which the compound is least soluble @ lower temp and soluble @ higher temp
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If there is an impurity present with your sample. . .
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there will be a depression in the melting point
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What is the role of iodine in the chemical reaction?
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Solvent stabilizer
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The product, benzopinacolone, form is a ___ rxn
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B form
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To calculate the yield of the product- what is the limiting reagent?
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Benzopinacol
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What is the oxidizing agent in the following rxn?
Borneol --NaOCl/Ch3COOH--> Camphor --NaBH4--> Isoborneol |
Sodium hypochlorite
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In the reduxn of camphor by NaBH4, 2 diastereoisomers are obtained- with what product?
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more exo product
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Which spectroscopy will be more useful and quickest to infer oxidxn of borneol to camphor?
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IR spectroscopy
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Which spectroscopy will be more useful in determining the ratio of exo & endo product in rxn of camphor by NaBH4?
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H NMR spectroscopy
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In the reduxn experiment of camphor to isoborneol - NaBH4 is used over LiAlH4 because?
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It is easier to handle
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What conclusion can we draw from the stereochemistry of isoborneol?
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Hydride is delivered to the endo face of camphor.
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What do we measure in an infrared spectrum?
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vibrational frequencies of chem bonds
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What peak will disappear from the IR of camphor when it is reduced by NaBH4?
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the peak at 2100-2200
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In the Tollen's test for the aldehyde, the shinning on the test tube comes from the formation of what?
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Silver metal
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What's the electrophile bromination of anisole?
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Br2
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Why is anisole more reactive to electrophilic bromination than benzene?
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The oxygen atom in anisole stabilizes the intermediate due to e- donation thru resonance.
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Why does anisole undergo electrophilic substitution rather than addition when treated with Br?
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the aromatic ring is very stable thus this stability is lost in an addition rxn.
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What is the major product of dibromonation of anisole?
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OCH3-Aromatic Ring-Br-Br
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What's the active electrophile in the electrophilic nitration of methyl benzoate?
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NO2+
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Why is methyl benzoate less reactive to electrophilic nitration than benzene?
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The ester group in methyl benzoate destabilizes the intermediate due to e- withdrawl thru resonance.
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Why does the methyl benzoate undergo meta substitution rather than para when treated with bromine?
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Meta groes through the most stable intermediate cation
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Why does nitration of methyl benzoate give only monosubstitution and no di or tri-substitution?
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the nitro group is strongly deactivation due to e- withdrawl thru resonance
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What is the 1st step in base-catalyzed aldol condensation?
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depronation of alpha carbon
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What's the last step in base-catalyzed aldol condensation?
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elimation of H2O
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What intermediate elimates water in aldol condensation to give an alpha, beta-unsat.ketone?
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Beta-hydroxy ketone
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What's the 1st step in mech. of the rxn bw p-aminophenol and acetic anhydride to form acetaminophen?
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Nucleophilic addition of p-aminophenol to acetic anhydride to form a tetrahedral intermediate.
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What's the last step in mech. of the rxn bw p-aminophenol and acetic anhydride to form acetaminophen?
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proton transfer from protonated amide to acetate anion
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How does sodium hydrosulfite remove the colored impurities in the crude acetaminophen?
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by a redox rxn
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How will you purify your acetaminophen after you decolorize it
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by recrystallization
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what kind of substance is acetaminophen?
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analgesic
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In chlorosulfonation of acetanilide, why do we protect aniline?
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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 |
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What is the 1st step in the mechanism of chlorosulfonation of acetanilide?
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Electrophilicattack of chlorosulfonic acid para to the acetamido group acetanilide.
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What is the 1st step in conversion of sulfonyl chloride to sulfonamide?
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Nucelophilic attack of ammonia at the sulfonyl chloride
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How do we remove the acetate protecting group from sulfanilamide?
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by acid-catalyzed hydrolysis
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What is a hazardous reagent?
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chlorosulfonic acid
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What type of rxn is the formation of methyl salicylate from salicylic acid and methanol?
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esterification
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What aton is protonated at the the first step in the mech.?
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the carbonyl oxygen atom of the carboxylic acid
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What is a hazardous agent?
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sulfuric acid
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What danger can occur from cracked glassware when performing a distillation at reduced pressure?
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an explosion
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