Orgo Lab Final Quiz

24 July 2022
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question
Do you expect chlorophyll b to be more or less polar than chlorophyll a? why?
answer
Chlorophyll b is more polar than chlorophyll a because chlorophyll a has a methyl group in the same position that chlorophyll b has an aldehyde
question
Do you expect xanthophyll to be more or less polar than B-carotene?
answer
Xanthophyll would be more polar than B-carotene because there is an alcohol on one of the phenol groups of xanthophyll
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Would you consider ethyl acetate to be a polar or non-polar solvent?
answer
I would consider ethyl acetate a polar solvent b/c the two oxygens pull the compound in different directions
question
Why do we mark TLC plates with pencil and not with pen?
answer
The ink from pen is polar so it will run up the TLC plate along with the TLC solvent
question
Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
answer
If one dilutes the initial sample prior to it being loaded onto the chromatography column, it would become a wide band in the column. You wouldn't be able to separate the compounds.
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How do you calculate Rf?
answer
(distance from origin to center of spot)/(distance from origin to solvent front)
question
A more polar compound would be closer or farther away from the origin point?
answer
closer
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Which compound would you expect to elute first from the column: unreacted ferrocene, acetylferrocene, or diacetylferrocene?
answer
Unreacted ferrocene would elute first from the column because it is the least polar of the group
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What is a monomer?
answer
the repeating units of polymers
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What is a repeating unit?
answer
some molecule that is binded together repeatedly until a polymer is formed
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What is condensation polymerization?
answer
reaction where molecules join together to form polymers
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What is a cross-linked polymer?
answer
a polymer formed from the linkage of two polymers
question
What are the layers formed when using interfacial polymerization from bottom to top?
answer
sebacoyl chloride -> hexamethylenediamine -> Nylon 10,6
question
Why cant we use vinyl alcohol in polymerization?
answer
Vinyl alcohol almost always exists as the tautomer
question
What is the purpose of sodium carbonate in the Dyeing lab?
answer
Sodium carbonate deprotonates napthol resulting in an alkoxide ion
question
Why do we add glacial acetic acid in Part 1B when we react with N, N-dimethylaniline, but we don't use it with the other aromatic coupling reagents?
answer
Glacial acetic acid catalyzes the aniline, but not completely
question
Which fabric was the most difficult to dye?
answer
Dacron (polyester)
question
Which fabric was the next most difficult to dye?
answer
Orlon
question
Which solvent ratio gave the best separation of the pigments? Why?
answer
50:50 ratio of hexane and ethyl acetate; It allowed there to be both a strong stationary phase and a strong moving phase
question
Which pigment in the spinach lab was the least polar?
answer
Beta-carotene because it went the highest on the TLC plate
question
Which pigment in the spinach lab was the most polar?
answer
chlorophyll B since it was the closest to the origin point
question
How do you explain the difference in polarity of the two chlorophylls in your sample?
answer
Chlorophyll b is more polar than chlorophyll a because chlorophyll b has an aldehyde in the same position that chlorophyll a has a methyl group
question
Why dont we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid?
answer
KMnO4 is a strong oxidizing agent and would oxidize the product past p-aminobenzoic acid
question
In the benzocaine step, why dont we do the esterification step prior to the deprotection step?
answer
the nitro group would also undergo esterification therefore resulting in a mixture of the products
question
What is a melting point?
answer
the temperature at which the solid phase is in equilibrium with the liquid phase
question
What is acetophentidin?
answer
a synthetic compound that acts as an analgesic and an antipyretic
question
What is an analgesic?
answer
Pain reliever
question
What is an antipyretic?
answer
fever reducer
question
What is the chemical name of acetophenetidin?
answer
4-ethoxyacetanilide
question
What are the two ways to make acetophenetidin?
answer
Williamson ether synthesis of p-acetamidophenol and Amide synthesis with p-phenetidine
question
How does recrystallization work?
answer
An impure sample is dissolved in a minimum amount of solvent at the boiling point. Any insoluble impurities are typically removed by hot gravity filtration. The hot, saturated solution is then allowed to cool slowly to room temperature
question
During the cooling process after recrystallization, what occurs?
answer
Small, pure seed crystals of the desired compound are formed in the solution. These seed crystals serve as nucleation sites where more molecules of the desired compound deposit themselves in layers
question
Why is the p-phenetidine sample reddish-brown?
answer
there is a small amount of impurities caused by air oxidation of the amino functional group in the compound
question
Why do we use decolorizing carbon in the acetophenetidin lab?
answer
to remove the colored impurities from the p-phenetidine sample
question
How do you calculate percent yield?
answer
(actual yield/theoretical yield) x 100
question
What is the best recrystallization solvent for acetophenetidin?
answer
water
question
How do you calculate theoretical yield?
answer
moles of limiting reagent X molecular weight of product
question
What is extraction?
answer
a technique that chemists use to remove selected components from a mixture, usually based on solubility differences or chemical reactivity
question
Solid-liquid extractions are usually performed with...
answer
liquid CO2
question
What does immiscible mean?
answer
not soluble in each other
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Whats the difference between extracting and washing?
answer
In extractions, you are pulling the compound from one thing to another. When washing, you are simply trying to get rid of impurities.
question
Draw an electrophilic aromatic substitution?
answer
Draw it bitch (pg. 63)
question
Why do the functional groups that are already present on the aromatic ring influence the placement of new substituents?
answer
The intermediate formed in the EAS reaction is a charged species that is stabilized by resonance
question
In the EAS lab, why do we use sodium iodide and household bleach?
answer
Sodium iodide is the source of iodine and bleach is the oxidizer
question
What was the color change during the iodination of salicylamide?
answer
Reaction went from orange-yellow to pale green
question
What is the mobile phase?
answer
when the mixture is placed in a gas or liquid phase
question
What is the stationary phase?
answer
a solid support that contains the absorbent
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The components of the sample mixture pass through the stationary phase as areas of concentration called...
answer
bands
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What is the eluent?
answer
the solvent that is used for the mobile phase
question
What is one way in which chain addition and condensation polymerization is different?
answer
a chain addition usually involves a vinyl-type monomer
question
In the Benzocaine lab, what does a purple halo with brown in the middle during the halo test mean?
answer
There are still unreacted reagents present in the reaction mixture and you need to continue heating
question
In the benzocaine lab, if the purple halo is no longer present, what has occurred?
answer
The oxidation of the methyl group is finished and the reaction is complete
question
What color should the solution be after boiling and passing the halo test in the benzocaine lab?
answer
colorless or light pink
question
What were the steps in the Benzocaine experiment?
answer
Protection, deprotection, esterification