Orgo Chem Lab Final

Salicylamide is an active ingredient in BC powder, a common OTC remedy. What is its purpose?

It enhances plasma levels of aspirin in the hopes of decreasing pain levels.

Calculate the amount (in grams) of salicylamide and sodium iodide needed for this experiment.
Given:
7.5mmol of Salicylamide MW=137.14 g/mol
8mmol of Sodium iodide MW=149.894

7.5mmol x 1mol/1000mmol x 137.14g/1mol = 1.028g 8mmol x 1mol/1000mmol x 149.894g/1mol = 1.199g

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?

OH is an activating, ortho/para directing substituent. The amide group is deactivating meta directing substituent. Combining both effects, the 3 and 5 positions appear to be most favorable. They overlab with the most negativity.

Electron Withdrawing group EWG
vs
Electron Donating group EDG

EWG - Withdraws electrons from aromatic ring -Amide in our experiment -Forms + charges on meta positions of ring -Deactivates ring EDG - Adds electrons to the ring -Forms - charges on ortho/para positions -Activates aromatic ring

"Insitu"

Not adding the reactant directly, you are forming it int eh solution to then use in another reaction

Is chlorophyl A or B more or less polar and why

Chlorophyl B in slightly more polar -B has a -CHO and A has a -CH3, the O makes B slightly more polar

Are Xanthophylls more or less polar than B-carotene? why?

B-carotene is a hydrocarbon and therefore is very nonpolar. Xanthophylls are more polar due to the oxygen they contain

Would you consider ethyl acetate to be a polar or non-polar solvent? why?

Moderately polar. The partial (-) charge from the oxygens and the partial (+) charge on the carbon are close enough to cancel each other though resonance.

Why do we mark TLC plates with pencil and not with pen

The ink in the pen could move on the plate with the sample, causing errors in data by adding new marks.

Which compounds on the tlc plate are more/less polar?

Farther up are less polar, than the lower ones

What is the purpose of the filter paper in the TLC lab

Help vaporize solvent system

Is silica polar or non polar?

Polar

What are you looking for in a good solvent system?

Good separation of the compounds

50:50 hexane to ethyl acetate
vs
70:30 hexane to ethyl acetate
when doing a TLC

The nonpolar solvent will move father, faster for the 70:30 and the polar solvent wont move as far, bc 70:30 is more non polar than 50:50.

What is TLC used for?

to test polarity

Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?

so that the entire sample enters the column in as compact of a band as possible. that eay you have better separation bt samples

Which compound would you expect to elute first from the column: unreacted ferrocene, acetylferrocene, or diacytylferrocene? why?

Unreacted ferrocine b/c it is the least polar

Why should you keep water out of the column?

because it is polar and it will mess up the solvent system

Why don't you want the column to dry out?

Silia layer will crack and the separation will happen unevenly

What are the sand layers for?

Bottom: to make the silica layer even and level for the separation to occur evenly across the column Top: When the solution splashes into column the sand protects the silica from becoming unlevel.

Monomer

Repeating units that are the building blocks of a polymer

Repeating unit

a group of atoms derived from a monomer and repeats throughout a polymer

Condensation polymerization

When 2 molecules react to form a larger unit while a small molecule, like H2O oir HCl Is eliminated.

Cross-Linked polymer

Polymer formed by polymers linking together though hydrogen bonds

Initiator

a molecule that starts the polymerization

Explain the purpose of the hot gravity filtration. Why is it good to use the stemless funnel for this technique?

The purpose of hot gravity filtration is to remove any insoluble impurities from your sample. It is better to use a stemless funnel because a funnel with a stem is prone to premature recrystallization.

What is ligroin? Is it polar or nonpolar?

Ligroin is a petroleum derivative, it is a volatile hydrocarbon mixture and is nonpolar.

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Orgo Chem Lab Final

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Salicylamide is an active ingredient in BC powder, a common OTC remedy. What is its purpose?

It enhances plasma levels of aspirin in the hopes of decreasing pain levels.

Calculate the amount (in grams) of salicylamide and sodium iodide needed for this experiment.
Given:
7.5mmol of Salicylamide MW=137.14 g/mol
8mmol of Sodium iodide MW=149.894

7.5mmol x 1mol/1000mmol x 137.14g/1mol = 1.028g 8mmol x 1mol/1000mmol x 149.894g/1mol = 1.199g

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?

OH is an activating, ortho/para directing substituent. The amide group is deactivating meta directing substituent. Combining both effects, the 3 and 5 positions appear to be most favorable. They overlab with the most negativity.

Electron Withdrawing group EWG
vs
Electron Donating group EDG

EWG – Withdraws electrons from aromatic ring -Amide in our experiment -Forms + charges on meta positions of ring -Deactivates ring EDG – Adds electrons to the ring -Forms – charges on ortho/para positions -Activates aromatic ring

"Insitu"

Not adding the reactant directly, you are forming it int eh solution to then use in another reaction

Is chlorophyl A or B more or less polar and why

Chlorophyl B in slightly more polar -B has a -CHO and A has a -CH3, the O makes B slightly more polar

Are Xanthophylls more or less polar than B-carotene? why?

B-carotene is a hydrocarbon and therefore is very nonpolar. Xanthophylls are more polar due to the oxygen they contain

Would you consider ethyl acetate to be a polar or non-polar solvent? why?

Moderately polar. The partial (-) charge from the oxygens and the partial (+) charge on the carbon are close enough to cancel each other though resonance.

Why do we mark TLC plates with pencil and not with pen

The ink in the pen could move on the plate with the sample, causing errors in data by adding new marks.

Which compounds on the tlc plate are more/less polar?

Farther up are less polar, than the lower ones

What is the purpose of the filter paper in the TLC lab

Help vaporize solvent system

Is silica polar or non polar?

Polar

What are you looking for in a good solvent system?

Good separation of the compounds

50:50 hexane to ethyl acetate
vs
70:30 hexane to ethyl acetate
when doing a TLC

The nonpolar solvent will move father, faster for the 70:30 and the polar solvent wont move as far, bc 70:30 is more non polar than 50:50.

What is TLC used for?

to test polarity

Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?

so that the entire sample enters the column in as compact of a band as possible. that eay you have better separation bt samples

Which compound would you expect to elute first from the column: unreacted ferrocene, acetylferrocene, or diacytylferrocene? why?

Unreacted ferrocine b/c it is the least polar

Why should you keep water out of the column?

because it is polar and it will mess up the solvent system

Why don’t you want the column to dry out?

Silia layer will crack and the separation will happen unevenly

What are the sand layers for?

Bottom: to make the silica layer even and level for the separation to occur evenly across the column Top: When the solution splashes into column the sand protects the silica from becoming unlevel.

Monomer

Repeating units that are the building blocks of a polymer

Repeating unit

a group of atoms derived from a monomer and repeats throughout a polymer

Condensation polymerization

When 2 molecules react to form a larger unit while a small molecule, like H2O oir HCl Is eliminated.

Cross-Linked polymer

Polymer formed by polymers linking together though hydrogen bonds

Initiator

a molecule that starts the polymerization

Explain the purpose of the hot gravity filtration. Why is it good to use the stemless funnel for this technique?

The purpose of hot gravity filtration is to remove any insoluble impurities from your sample. It is better to use a stemless funnel because a funnel with a stem is prone to premature recrystallization.

What is ligroin? Is it polar or nonpolar?

Ligroin is a petroleum derivative, it is a volatile hydrocarbon mixture and is nonpolar.

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