CHM2211L Final Prelab/Postlab Questions

5 September 2022
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question
What is the purpose of salicylamide?
answer
Salicylamide significantly enhances plasma levels of aspirin with potential therapeutic implications
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Consider the directing effects of the substituents on salicylamide and predict the possible structures of the iodination products. Which do you think will be the major product?
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OH is an activating, ortho/para directing substituent. The amide group is a deactivating meta directing substituent. Combining both effects the 3 and 5 position appear to be the most favorable (overlap with the most negativity)
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Do you expect chlorophyll b to be more or less polar than chlorophyll a?
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Chlorophyll b is slightly more polar than chlorphyll a. This is due to the fact that chlorophyll a has a methyl group in a position where chlorophyll b has an aldehyde
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Do you expect xanthophylls to be more or less polar than B-carotene?
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Xanthophylls are more polar than B-carotene because xanthophylls contain oxygen atoms, while carotenes are purely hydrocarbons with no oxygen
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Would you consider ethyl acetate to be a polar or non-polar solvent?
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Moderately polar due to dipole moment of oxygen atom and presence of ester
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Why do we mark TLC plates with pencil and not with pen?
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Ink from the pen will dissolve and be separated, which could interfere with the results
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If TLC plate is developed in ligroin, how can you tell which compound is the most polar?
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Compound that travels the least distance
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How would the Rf values change if a more polar solvent (like ethyl acetate) were used?
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Compounds would travel faster because the more polar eluting solvent is more proficient at eluting the compounds from the polar slide. Thus, each of the compounds would have a larger Rf value.
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Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
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So that the entire sample enters the column in as compact of a band as possible
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Which compound would you expect to elute first from the column: unreacted ferrocene, acetylferrocene, or diacetylferrocene?
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Unreacted ferrocene because it is least polar
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The tricky part of this multi-step synthesis is the isolation of the neutral p-aminobenzoic acid in step 3. Why is this isolation so difficult?
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It is more soluble in water
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monomer
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a molecule that forms the basic unit for polymers; can bind to other monomers to form a repeating chain molecule
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repeating unit
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the fundamental recurring unit of a polymer
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condensation polymerization
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reaction in which molecules join together but lose small molecules as by-products, such as water or methanol
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cross-linked polymer
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a polymer that includes interconnections between chains, either formed during polymerization (by choice of monomer) or after polymerization (by adding a specific reagent)
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Why can't we use vinyl alcohol in the polymerization of PVA?
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It will form several ether linkages
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Why is HCl used instead of just plain deionized water in the synthesis of acetophenetidin?
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HCl's polarity contributes to a reaction driven to the right; the HCl protonates the amine group, making it more soluble and easier to dissolve
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What is the purpose of the sodium acetate solution in the amide synthesis of acetophenetidin?
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buffer the reaction mixture
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extracting
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a product is removed from a mixture, leaving the impurities behind
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washing
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unwanted impurities are removed from a mixture, leaving the product in the original solution
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What do your results tell you about the directing effects of the substituents on salicylamide?
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Salicylamide has a hydroxyl group on the ring that is a strongly activating, electron donating substituent, while the amide group is electron withdrawing. The electron donating group, hydroxyl, directed the incoming iodide to the para position
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Which solvent ration gave the best separation of the pigments?
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50:50 hexane/ethyl acetate
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Which of the pigments is the least polar?
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hexane (ligroin)
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Which of the pigments is the most polar?
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ethyl acetate
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Which diacetylferrocene isomer formed?
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1,1-diacetylferrocene
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When dyeing with your azo dye, which fibers seemed to interact best with the dye?
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nylon 6,6, silk, and wool
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Did you notice any significant changes when the Congo red fabric was treated with acid?
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produced shades of blue-violet; acid protonates the dye
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How can you tell that white indigo is the reduced form?
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reduced form contains two alcohol groups, while the oxidized form has two carbonyl groups
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What chemical process happens as the fabric dries?
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oxidation
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Which of the fabrics were most resistant to dyeing?
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Dacron (polyester) and Orlon (polyacrylonitrile); they lack sufficient areas for the dye to react and may lack necessary functional groups
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Why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid?
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KMnO4 is a strong oxidizing agent and cannot be guaranteed to stop reacting at the p-aminobenzoic acid stage; it could continue oxidizing to NO2
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Why don't we do the esterification step prior to the deprotection step?
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to ensure protection of the desired compound; esterification step is so important because it leads to the formation of esters and the elimination of water molecules
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pKa of alcohol
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17
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pKa of carboxylic acid
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4
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Purpose of brine?
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to remove the majority of dissolved water
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Why is a brown color observed during EAS?
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The brown color observed is due to the formation of molecular iodine I2