sharp melting point, range is narrow (1-2 degrees)
  • Heterogeneous Mixture
  • Pure Element
  • Pure Compound
  • Ethyl Acetate
Allows the reaction to be carried out at the boiling point of the solvent and yet it prevents loss of solvent or reagent due to evaporation. The vapors condense as they rise up the condenser and thus prevent them from escaping.
  • Soxhlet apparatus
  • Babcock bottle
  • Aspirator
  • Reflux condenser
Since cloves are dried up, soaking them would allow water to penetrate into the cloves and more eugenol would be isolated.
  • What is extraction? What types are there?
  • Why is it important to soak the clover in water?
  • What is the purpose of crushing magnesium turnings?
  • What is the reaction of the first step? (Protection)
small stretches from 1500-2000
  • presence of benzene rings (IR)
  • IR: -C=C
  • C-O (IR)
  • What is the purpose of salicylamide?
travels more slowly
  • how to remove reddish brown from p-phenetidine?
  • What is the purpose of crushing magnesium turnings?
  • If a component has a greater affinity for the stationary phase
  • Charged intermediate species
most widely used herbal remedies, treating various ailments including asthma, macular degeneration, cardiovascular disease, vertigo, and memory loss and dementia associated with Alzheimer's disease
  • Cocaine
  • Aloe vera
  • St. john's wort
  • Ginkgo biloba
The two solvents that are chosen for the extraction must be immiscible. In addition, the compound to be extracted must have different affinities for the two solvents.
  • What was the best recrystallization solvent for the acetophenetidin?
  • Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
  • What is the purpose of the sodium acetate solution in the amide synthesis?
  • What criteria must be met in order for a liquid-liquid extraction to be successful?
B-carotene is the least polar and chlorophyll b is the most polar
  • Which pigment is the least polar which is the most?
  • Why should you not stir the crystals in the buchner funner?
  • What does absolute ethanol do to the salicylamide?
  • What is extraction? What types are there?
no since both are very close in acidity; cannot use reagents in this experiment to neutralize one and keep one (stronger acid) as a weak acid; both would be neutralized
  • Why is dichloromethane (CH2Cl2) added to the solution in the collection vessel? What process is this called?
  • Which compound would elute first from the column: unreacted ferrocene, acetylferrocene, or diacetylferrocene? Why?
  • Could you separate 2,4-dinitrophenol (pH 3.96) from benzoic acid using extraction procedure IN THIS EXPERIMENT?
  • Why does the presence of a soluble impurity in a sample has the effect of lowering and broadening the melting point range?
iodination reactions using sodium iodine as the source of iodine and household bleach as an oxidizer (instead of nitric acid and I2)
  • Errors of taking melting points:
  • sodium thiosulfate
  • Carboxylate ions + HCl solution
  • Green method for EAS:
Recrystallization using ethanol. The desired compound is soluble in ethanol at boiling point and is insoluble in ethanol when it cools.
  • After all of the ether has evaporated, what can we do to purify the organic solid?
  • Why don't we do the esterification step prior to the deprotection step?
  • When the reaction mixture is added to the separatory funnel with diethyl ether what happens? Where is the desired compound?
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
To load the sample onto the top of the column
  • What is the goal of pipets full of ligroin after addition of crude sample of acetylferrocene?
  • What is the purpose of salicylamide?
  • What is the perfect composition of the eluent for the spinach lab?
  • What is present in the organic layer? What steps do you need to take to isolate the desired product?
pure ethyl acetate
  • Reducing the number of steps in synthesis:
  • If carboxylic compounds remain aqueous
  • Solvent for diacetyl ferrocene:
  • TLC of acetylferrocene: eluent
has many sites for hydrogen bonding; polar compounds would interact with the silva and adsorb readily to the stationary phase
  • Silica gel
  • Mobile phase
  • Stationary phase
  • Ethyl acetate
solvent derived from petroleum consisting of C7 and C8 hydrocarbon, non polar
  • UV Light for TLC
  • Amide synthesis of acetophenetidin
  • ligroin
  • NH2 (IR)
removes any residual iodine from the solution
  • gold chloride
  • oxalic acid
  • sodium thiosulfate
  • sodium hypochlorite
we cant oxidize p-touluidine with KMnO4 because the NH2 must first be protected or else it would be oxidized also. the side product would have been a R-NOO-
  • How would the Rf values change if a more polar solvent (like ethyl acetate) were used?
  • why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid? wouldn't that be faster? what unwanted reactions may occur?
  • How do you test for the completion of reaction with magnesium sulfate, n-acetyl-p-toluidine, and potassium permanganate?
  • why is it important that the glassware and reagent used in a Grignard reaction are completely dry?
HCl protonates p-phenetidine and drives the reaction to the right but too much HCl would convert all of the compound to its conjugate acid and no reaction with acetic anhydride would occur. Sodium acetate creates a buffer within the reaction that would control HCl's acidity.
  • What is the purpose of the sodium acetate solution in the amide synthesis?
  • Describe the practical reasons behind the direction of the flow of water through condenser:
  • What is the directing effects of the substituents on salicylamide?
  • What is the purpose of crushing magnesium turnings?
There more stable or the weaker the conjugate base, the more acidic the compound is. When losing a proton, phenol's conjugate base has resonance stability from its double bond.
  • Why is iodine used instead of chlorine and bromine?
  • Why is carbon dioxide used as a solvent for solid-liquid extractions?
  • Why is it important to soak the clover in water?
  • Why is phenol much more acidic than cyclohexanol
1) p-acetamidophenol +sodium methoxide, methanol, and ethanol2) 1st product (addition of sodium) + Bromoethane
  • Reductive Amination
  • Reaction Of Acetic An Hydride
  • Williamson Ether Synthesis
  • Phenol And Ether + Brine
acidify the aqueous solution which drives the products to precipitates
  • 1M hydrochloric acid
  • 0m hydrochloric acid
  • 99m hydrochloric acid
  • 5m hydrochloric acid
immiscible (ether top)
  • ether and water
  • salt and ketones
  • lipids and water
  • ester and water
Non-polar or least polar compound elute first and therefore unreacted ferrocene elute first because it has no polar group. Acetylferrocene elute seconds because it only has 1 polar C=O group compared to diacetylferrocene which would elute last with 2 polar C=O groups.
  • Which compound would elute first from the column: unreacted ferrocene, acetylferrocene, or diacetylferrocene? Why?
  • Why can you not introduce water into the chromatography column?
  • What is the purpose of the sodium acetate solution in the amide synthesis?
  • Why is dichloromethane (CH2Cl2) added to the solution in the collection vessel? What process is this called?
miscible
  • Hexane vs water
  • Ethanol vs. water
  • Treating NaOH vs NaHCO to the carboxylic-phenol mixture
  • Why does the williamson ether synthesis take two steps?
because the compounds being separated will oxidize rapidly on exposure to air so it would fade away
  • Why do we need to take pictures of TLC plates during lab?
  • Why is acetone used in chlorophyll extraction?
  • Why is iodine used instead of chlorine and bromine?
  • Why do we have to cover the test tube of acetone and spinach mixture with parafilm?
EAS with Cl2 and Br2 can occur in the presence of Lewis acid such as AlCl3, BUT iodine is the least reactive of the halogens
  • Why is phenol much more acidic than cyclohexanol
  • Why should you not stir the crystals in the buchner funner?
  • Why is acetone used in chlorophyll extraction?
  • Why is iodine used instead of chlorine and bromine?
brine and anhydrous magnesium sulfate
  • To dry the CH3Cl2:
  • To dry the CH2Cl2:
  • To dry the CH2Cl102:
  • To dry the CH0Cl2:
Williamson ether synthesis
  • Green method for EAS:
  • p-acetamidophenol
  • Melting Point
  • Phenol and Ether + BRINE
this protonates carboxylate ions back into carboxylic acid compounds that forms solids when put in ice bath
  • Green method for EAS:
  • Why cant you let the Celite dry out?
  • Carboxylate ions + HCl solution
  • For step 3- why do you need to scratch the wall of the flask?
100-74.97-8.39 = 16.64% O# of C: 74.97/12 = 6.25/1.04 = 6# of H: 8.39/1=8.39/1.04= 8# of O: 16.64/16 = 1.04/1.04 = 1EmF: C6H8O
  • What was the best recrystallization solvent for the acetophenetidin?
  • why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid? wouldn't that be faster? what unwanted reactions may occur?
  • Can IR spectroscopy be used to distinguish 2-pentanone from 2-hexanone? why or why not?
  • An unknown compound was determined to be 74.97% C, 8.39% H, and no nitrogen. What is the empirical formula
HCl is a much stronger acid which protonates the amine group of the p-phenetidin, which makes it more soluble in the solution
  • Why is HCl used instead of just DIW?
  • Why should you not stir the crystals in the buchner funner?
  • Why do we need to take pictures of TLC plates during lab?
  • Why is acetone used in chlorophyll extraction?
Ethyl acetate is a polar compound while hexane is non polar; one compound interacts with the polar compounds of spinach while the other with the non polar compounds. The 50:50 ratio was enough to separate the polar and non polar compounds of the spinach, at the same time, the polar compounds also get to move up from the origin due to its interaction with the ethyl acetate. If only hexane was use, the chlorophyll a and b would remains at the origin and would not be separated form one another.
  • Why is HCl used instead of just DIW?
  • What takes place during a Grignard reaction?
  • What is present in the organic layer? What steps do you need to take to isolate the desired product?
  • Why is a 50:50 ratio the best for this case?
small amount of impurities caused by air oxidation of the amino functional group
  • What is the purpose of crushing magnesium turnings?
  • Why is the reaction mixture added to hydrosulfuric acid and ice?
  • Why is the sample of p-phenetidine reddish brown?
  • What is the reaction what would happen if phenyl magnesium bromide reacts with water
Chlorophyll b should be more polar than chlorophyll a because the former has a CHO group where the latter only has a CH3 group.
  • Is chlorophyll b more or less polar than chlorophyll a?
  • Why do we need to take pictures of TLC plates during lab?
  • Why is acetone used in chlorophyll extraction?
  • Why is iodine used instead of chlorine and bromine?
- Hot gravity filtration serves to remove any insoluble impurities that do not dissolve when the solution is brought to its boiling point.- it is good to use the stemless funnel for this technique because this would minimize any contact between the hot solution and the funnel. If a funnel with stem is used the droplets of hot solution might get stuck on the stem inner surface and early crystallization of the solution might occur
  • Could you separate 2,4-dinitrophenol (pH 3.96) from benzoic acid using extraction procedure IN THIS EXPERIMENT?
  • What is the difference between "extracting" and "washing"?
  • Why is the reaction mixture added to hydrosulfuric acid and ice?
  • Explain the purpose of the hot gravity filtration. Why is it good to use the stemless funnel for this technique?
is an oxidizing agent that reacts with sodium iodine and turns it from a stable compound to a strong electrophile that would now react with the salicylamide in the electrophilic aromatic substitution
  • 6% sodium hypochlorite solution (household bleach)
  • Why don't we do the esterification step prior to the deprotection step?
  • Why is the reaction mixture added to hydrosulfuric acid and ice?
  • why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid? wouldn't that be faster? what unwanted reactions may occur?
Major product gives the less strained position of Iodine that followings the directing effect of both substituent: meta to NH2 and ortho to OH
  • Why is the reaction mixture added to hydrosulfuric acid and ice?
  • Why is the sample of p-phenetidine reddish brown?
  • What is the purpose of the sodium acetate solution in the amide synthesis?
  • What is the directing effects of the substituents on salicylamide?
Water because the solute is completely soluble at boiling point, but the crystals reappear when solution is placed in an ice bath.
  • What is the reaction what would happen if phenyl magnesium bromide reacts with water
  • What was the best recrystallization solvent for the acetophenetidin?
  • Why can you not introduce water into the chromatography column?
  • why must the solution of KMnO4 be hot when filtering using the Celite bed?
They serve as nucleation sites where more molecules of the desired compound deposit themselves in layers.
  • Pencil for TLC plates?
  • Why is HCl used instead of just DIW?
  • Carboxylate ions + HCl solution
  • What do seed crystals do?
PARA is difficult to isolate because it has so many resonance that the compound can have many charges on it at different pH. Isoelectric point is where the compound carries not net charges, containing equal amount of (+) and (-) that neutralize each other. It is where it is easiest to gain precipitates and therefore its is very unstable and sensitive to pH.
  • What is present in the organic layer? What steps do you need to take to isolate the desired product?
  • Why is isolating neutral p-aminobenzoic acid in step 3 difficult?
  • Why is ferrocene called the super aromatic molecule?
  • What is the difference between "extracting" and "washing"?
120-122°C
  • Mandelic acid
  • P-phenetidine
  • Sulfuric acid
  • Benzoic acid
with distillation, cloves are allowed to sit in water for full penetration which would be more advantageous because it would yield higher % of product. Extraction using CO2 reduces the chance of water remnant and impurities. CO2 extraction would produce better quality result; during the heating process of distillation, a lot of quality from the oil is evaporated
  • After all of the ether has evaporated, what can we do to purify the organic solid?
  • What is the difference between "extracting" and "washing"?
  • Advantages and disadvantages of distillation vs. CO2 extraction:
  • Comparing TLC plates: did chromatography serve to purify the sample?
It offers a greener alternative to other solvents, it is readily available, nonflammable, nontoxic, and safe for the environment. Ease of removal of solvent at the end of procedure, and it is relatively quick.
  • Why is the reaction mixture added to hydrosulfuric acid and ice?
  • Can IR spectroscopy be used to distinguish 2-pentanone from 2-hexanone? why or why not?
  • Why is carbon dioxide used as a solvent for solid-liquid extractions?
  • How would the Rf values change if a more polar solvent (like ethyl acetate) were used?
use ETHER for back extraction
  • Carboxylate ions + HCl solution
  • If carboxylic compounds remain aqueous
  • Charged intermediate species
  • Reducing the number of steps in synthesis:
because the drop would dry out and channels can form in the packing material which leads to inappropriate, poor separation.
  • Can IR spectroscopy be used to distinguish 2-pentanone from 2-hexanone? why or why not?
  • Why is phenol much more acidic than cyclohexanol
  • What is the directing effects of the substituents on salicylamide?
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
the eluent, the has or liquid phase in which the sample mixture is placed in
  • Mobile phase
  • Silica gel
  • Stationary phase
  • Chromatography
acetic anhydride reacts with phosphoric acid to form asylum ion which is an electrophile that can be used to add into an aromatic ring
  • Why is HCl used instead of just DIW?
  • Oxidation reaction
  • Reaction of acetic an hydride
  • Errors of taking melting points:
stabilized by resonance
  • Phenol and Ether + BRINE
  • Charged intermediate species
  • Ethyl acetate
  • Pure Compound
increase % yield
  • Reducing the number of steps in synthesis:
  • Why cant you let the Celite dry out?
  • If a component has a greater affinity for the stationary phase
  • What is the reaction of the first step? (Protection)
70:30 ligroin:ethyl acetate
  • How to elute ferrocene?
  • For step 3- why do you need to scratch the wall of the flask?
  • More polar solvent that is used to elute acetylferrocene
  • What is the purpose of salicylamide?
Grignard reagent is extremely sensitive and reactive with water. Since it is a strong nucleophile it would react with water first and will not be able to produce the desirable reaction and product
  • Why is carbon dioxide used as a solvent for solid-liquid extractions?
  • Why is iodine used instead of chlorine and bromine?
  • why is it important that the glassware and reagent used in a Grignard reaction are completely dry?
  • Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
UV lights activates a fluorescent indicator on the plates
  • sodium thiosulfate
  • UV Light for TLC
  • Stationary phase
  • To dry the CH2Cl2:
NaOH is so strong that it would neutralized both strong acid such as carboxylic acid and weaker ones like phenol. On the other had NaHCO3 is weak enough that it can only react with strong carboxylic acid and remains unreacted with phenol
  • Advantages and disadvantages of distillation vs. CO2 extraction:
  • Why is isolating neutral p-aminobenzoic acid in step 3 difficult?
  • Which one is more polar? B-carotene vs. xanthophyll
  • Treating NaOH vs NaHCO to the carboxylic-phenol mixture
if esterification occur prior to deprotection then both functional would would be deprotected and we would have to report esterification.
  • Why don't we do the esterification step prior to the deprotection step?
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
  • What was the best recrystallization solvent for the acetophenetidin?
  • What is the directing effects of the substituents on salicylamide?
improper amount of sample in capillary tube 2) mistaking sagging or shrinking sample as melting 3) presence of solvent cause crystals to "sweat"
  • Electrophilic aromatic substitution
  • What takes place during a Grignard reaction?
  • Pencil for TLC plates?
  • Errors of taking melting points:
the ink in the pen can tamper with the process; the ink would travel up the TLC plate with the solvent
  • Mobile phase
  • Why cant you let the Celite dry out?
  • Pencil for TLC plates?
  • Anhydrous Magnesium Sulfate
needs to boil gentle: too little heat will keep the reaction from occurring at a good time, too much heat will cause excessive frothing and possible boo over
  • Oxidation reaction
  • Elimination reaction
  • Oxidation
  • Activation energy
H between I -NH2: 8.15 ppm (singlet)H closer to I (between I and O): 7.7 ppm (doublet)H closer to O (between I and O): 6.75ppm (doublet)
  • Silica gel
  • Interpret NMR:
  • What do seed crystals do?
  • Chromatography
When a more polar solvent is used instead of non polar one like ligroin, it will interact more with the polar molecules and less with the non polar molecules causing a less dramatic separation. Rf values would be higher.
  • What is the directing effects of the substituents on salicylamide?
  • How would the Rf values change if a more polar solvent (like ethyl acetate) were used?
  • What criteria must be met in order for a liquid-liquid extraction to be successful?
  • why must the solution of KMnO4 be hot when filtering using the Celite bed?
At the isoelectric pt. the desirable precipitate will form, more acidic = salt precipitates (NH3+), more basic = no precipitate1) add 3M NH4OH solution --> decrease pH to isoelectric pt2) Adjust pH of the filtrate until it is just basic3) adjust pH again with glacial acetic acid
  • mechanism of Step three (Deprotection)
  • Why is HCl used instead of just DIW?
  • Electrophilic aromatic substitution
  • Why is phenol much more acidic than cyclohexanol
a solid support that contains an adsorbent
  • Column
  • Mobile phase
  • Stationary phase
  • Chromatography
Extraction and washing can share very similar procedure but ultimately have different purposes. Extraction removes desire compounds/solutions from a mixture whereas washing filters out the impurities from the desired solution. Keep extraction and discard washed impurities.
  • What is the purpose of crushing magnesium turnings?
  • What is the difference between "extracting" and "washing"?
  • What is the perfect composition of the eluent for the spinach lab?
  • What was the best recrystallization solvent for the acetophenetidin?
3200-3300 (double peaks)
  • IR: -NH12
  • IR: -NH0
  • IR: -NH10
  • IR: -NH2
Since the compound is very non polar due to the lack of O group, it can only be remove through a workup step using a non polar substance. By adding the cold ligroin, the biphenyl would be removed which followed the ligroin down the Buchner funnel.
  • Common bi product o the Grignard Reaction lab is biphenyl which is generated through a coupling reaction of phenyl magnesium bromide with unreacted bromobenzene. Which part of the workup remove this byproduct?
  • Explain the purpose of the hot gravity filtration. Why is it good to use the stemless funnel for this technique?
  • Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
  • why is it important that the glassware and reagent used in a Grignard reaction are completely dry?
Grignard reagents are sensitive to water so if diethyl either containing more water is used it will interfere with the formation of the Grignard reagent.
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
  • Why must bromobenzene be mixed with anhydrous diethyl ether during formation of the Grignard reagent?
  • Why is dichloromethane (CH2Cl2) added to the solution in the collection vessel? What process is this called?
  • Why don't we do the esterification step prior to the deprotection step?
immiscible (Hexane top)
  • Hexane vs water
  • TLC of acetylferrocene: eluent
  • NH2 (IR)
  • Ethanol vs. water
An aqueous layer forms (bottom) and an organic layer forms (top). The desired compound is dissolved in the organic layer (like dissolves like).
  • When the reaction mixture is added to the separatory funnel with diethyl ether what happens? Where is the desired compound?
  • Why does the presence of a soluble impurity in a sample has the effect of lowering and broadening the melting point range?
  • why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid? wouldn't that be faster? what unwanted reactions may occur?
  • What is present in the aqueous layer you drained? How do you neutralize it? How do you isolate it?
3450.1
  • IR: -OH
  • OH (IR)
  • C-H (IR)
  • IR: -C=C
Acetone evaporates extremely quickly when interacting with air and all the solution would evaporate
  • Why don't we do the esterification step prior to the deprotection step?
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
  • Why do we have to cover the test tube of acetone and spinach mixture with parafilm?
  • Why should you not stir the crystals in the buchner funner?
Because the hydrogen on the alcohol group of acetamidophenol would react with the bromoethane to create ethane and there would not be any reaction. The sodium acetate turns that alcohol group into a nucleophile that would attack the C of the bromoethane
  • Why does the williamson ether synthesis take two steps?
  • Considering 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?
  • What was the best recrystallization solvent for the acetophenetidin?
  • Ethanol vs. water
immiscible (Water top)
  • Methylene chloride vs water
  • Treating NaOH vs NaHCO to the carboxylic-phenol mixture
  • Ethanol vs. water
  • Which one is more polar? B-carotene vs. xanthophyll
xanthophyll would be more polar than B-carotene because of the -OH group at the ends of the molecules. B-carotene contains no oxygen and is quite non polar.
  • Advantages and disadvantages of distillation vs. CO2 extraction:
  • Which one is more polar? B-carotene vs. xanthophyll
  • What takes place during a Grignard reaction?
  • Comparing TLC plates: did chromatography serve to purify the sample?
Helps expose fresh metal surface by removing some magnesium oxide on the exterior.
  • What is the purpose of salicylamide?
  • Why is it important to soak the clover in water?
  • What does absolute ethanol do to the salicylamide?
  • What is the purpose of crushing magnesium turnings?
no effect
  • Why don't we do the esterification step prior to the deprotection step?
  • What criteria must be met in order for a liquid-liquid extraction to be successful?
  • What effects does insoluble impurity like sand and glass has on MP?
  • What is the directing effects of the substituents on salicylamide?
distance from the origin to the center of the spot DIVIDED BY the distance form the origin to the solvent front; Polar compounds interacts more strongly with stationary phase and travel a shorter distance --> the more polar the compound, the smaller the Rf values
  • Mobile phase
  • Chromatography
  • Stationary phase
  • Rf value
this will cause cracks in the filter bed and result in insufficient filtration
  • Why cant you let the Celite dry out?
  • Anhydrous Magnesium Sulfate
  • Why can you not introduce water into the chromatography column?
  • Amide synthesis of acetophenetidin
While for aldehydes and ketones, after the first Grignard reaction, there is nothing left to react, for esters, after the first reaction the compound becomes a keno or aldehyde and can drive further Grignard reaction
  • Why does the presence of a soluble impurity in a sample has the effect of lowering and broadening the melting point range?
  • Why must bromobenzene be mixed with anhydrous diethyl ether during formation of the Grignard reagent?
  • Why aldehydes and ketone add only one equivalent of Grignard reagent, but esters added two equivalent
  • why don't we simply oxidize p-toluidine with KMnO4 to make p-aminobenzoic acid? wouldn't that be faster? what unwanted reactions may occur?
1,1'-diacetylferrocene would be the isomer present. If 1,2 and 1,3-diacetylferrocene were to be formed, both C2 and C3 would have to be able to accept the acetyl group which means those position has to be nucleophilic. However if looked at the resonance structure of those positions, those carbon has the tendency to be positively charged which means they are electrophilic and would not be able to accept acetyl group. Therefore acetyl group at C1 an C1' is the best option
  • Use knowledge of the mechanism and theory of electrophilic aromatic substitution to explain the formation of the diacetylferrocene isomer:
  • When the reaction mixture is added to the separatory funnel with diethyl ether what happens? Where is the desired compound?
  • What is present in the aqueous layer you drained? How do you neutralize it? How do you isolate it?
  • Which compound would elute first from the column: unreacted ferrocene, acetylferrocene, or diacetylferrocene? Why?
N - 8ppmCH3 (acetyl group) - 2ppmH(2) (closer to N)- 7.4 ppmH(2) (closer to O)- 6.8-7ppmCH2 (closest to O)-4 ppmCH3 (closet to O) - 1.4 ppm
  • Why is acetone used in chlorophyll extraction?
  • Chromatography
  • NMR of acetylphenetidin
  • What do seed crystals do?
1500
  • presence of benzene rings (IR)
  • C=C (IR)
  • Phenyl (IR)
  • C-O (IR)
The phenol is present. There may be some water present in the solution so it must be dried with brine and anhydrous magnesium sulfate until it no longer clumps together. The drying agent is then separated from the organic solution through gravity filtration. Once this is done, the ether must be evaporated under reduced pressure so that the pure phenol solid is left in the flask.
  • Why is carbon dioxide used as a solvent for solid-liquid extractions?
  • What is present in the organic layer? What steps do you need to take to isolate the desired product?
  • why is it important that the glassware and reagent used in a Grignard reaction are completely dry?
  • What criteria must be met in order for a liquid-liquid extraction to be successful?
because the impurity disrupts the crystalline lattice of the sample so less energy is required to convert the solid phase into a liquid phase
  • Why must the apparatus be flame dried prior to the beginning the reaction?
  • Why cant you allow the volume of solvent to go below the top of the adsorbent?
  • Why does the presence of a soluble impurity in a sample has the effect of lowering and broadening the melting point range?
  • why must the solution of KMnO4 be hot when filtering using the Celite bed?
methylene chloride
  • Why cant you let the Celite dry out?
  • What do seed crystals do?
  • how to remove reddish brown from p-phenetidine?
  • TLC of acetylferrocene: eluent
helps with gentle boiling
  • Wooden applicator
  • Fingers
  • Metal applicator
  • Cotton pads
decolorizing carbon
  • how to remove reddish brown from p-phenetidine?
  • How to elute ferrocene?
  • What is the perfect composition of the eluent for the spinach lab?
  • If the p-toluidine in water+HCl is excessively dark,what would you do?
Acetone breaks down chlorophyll's lipid bonds to a plant's thylakoid structure and suspends the pigment in solution.
  • What is the reaction of the first step? (Protection)
  • Why is acetone used in chlorophyll extraction?
  • Why is phenol much more acidic than cyclohexanol
  • Why do we need to take pictures of TLC plates during lab?
common reaction of benzene and its derivatives; two steps: 1) aromatic ring acts as a nucleophile and attack electrophile 2) aromatic ring is regenerated through the loss of proton
  • Electrophilic aromatic substitution
  • Base catalyzed aldol reaction
  • Wolff-kishner reduction
  • Electrophilic addition
the column chromatography served its purpose of separating and purifying samples. with the crude sample there are ferrocene, acetylferrocene and diacetylferrocene all present in the product. After purifying through the chromatography column, only acetylferrocene was collect.
  • What is the difference between "extracting" and "washing"?
  • For step 3- why do you need to scratch the wall of the flask?
  • Comparing TLC plates: did chromatography serve to purify the sample?
  • Hexane vs water
1095.3
  • IR: -CO
  • Ethyl acetate
  • presence of benzene rings (IR)
  • Silica gel
travels thought the stationary phase more quickly
  • How does iodine help facilitate the reaction of the magnesium turnings?
  • If the p-toluidine in water+HCl is excessively dark,what would you do?
  • What does absolute ethanol do to the salicylamide?
  • If a component has a greater affinity for the mobile phase
Water is very polar and should not be in the mix of the chromatography column. If water is present, it would interact with the acetylferrocene and diacetylferrocene and the whole solution would travel down together with no separation
  • Why can you not introduce water into the chromatography column?
  • Why must the apparatus be flame dried prior to the beginning the reaction?
  • Why is phenol much more acidic than cyclohexanol
  • Why don't we do the esterification step prior to the deprotection step?
First bromobenzene reacts with magnesium to form phenyl magnesium bromide. Then by adding the electrophile, the PMB would nucleophilically attack the compound.
  • What takes place during a Grignard reaction?
  • Why is phenol much more acidic than cyclohexanol
  • Why is HCl used instead of just DIW?
  • What is extraction? What types are there?
The more concentrated sample would produce a more significant or finer separation between polar and non polar compounds. Diluting the sample would cause a blurry separation between complex compounds instead of a fine separation
  • Why is it important not to dilute the initial sample before it has been loaded onto the chromatography column?
  • why is it important that the glassware and reagent used in a Grignard reaction are completely dry?
  • What is present in the aqueous layer you drained? How do you neutralize it? How do you isolate it?
  • Why must bromobenzene be mixed with anhydrous diethyl ether during formation of the Grignard reagent?
via halo test: dip the stirring rod into the mixture then touch the tip to a piece of filter paper --> purple halo = incomplete; light pink/clear halo = complete
  • How do you test for the completion of reaction with magnesium sulfate, n-acetyl-p-toluidine, and potassium permanganate?
  • What is present in the organic layer? What steps do you need to take to isolate the desired product?
  • When the reaction mixture is added to the separatory funnel with diethyl ether what happens? Where is the desired compound?
  • Why must bromobenzene be mixed with anhydrous diethyl ether during formation of the Grignard reagent?
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