Final Flashcards
air condenser
straight tube
casserole
clay cup on a stick
claisen adapter
tube that separates into two, U shaped
crucible tongs
go outward, for holding hot beakers and such
drying tube
tube that takes a hard right
Hickman still head
the tube that looks kinda squished down, tiny tube going into larger tube
jacked water condenser
two side ports, shell around tube
stirring rod with rubber policeman
glass rod, pointy rubber tip
sublimation adapter
short piece of glass with side port and slanted bottom
test tube clamp
holder part is little curved rectangles
thistle tube
looks like a vase on a stick
vacuum filter flask
large erlenmeyer with side port
Where are the safety showers? (2)
In both corners on the hallway side
Where are the fire blankets? (2)
In both corners on the hallway side, in the left corner the blanket is to the right of the cart
Where is the eyewash station? (1)
On the second station from the left
Where are the fire extinguishers? (3)
To the left of each hood when facing into the lab, and in the right corner by the hallway
(all three are on wall with door)
1,3-diphenylacetone
Ph-CH2-C(=O)-CH2-Ph
9-Fluorenol
Pentagon with -OH on top and part of two benzene rings on sides
*There is only one carbon not part of the benzene rings
Same as 9-hydroxyfluorene
9-Fluorenone
Pentagon with =O on top and part of two benzene rings on sides
*There is only one carbon not part of the benzene rings
9-hydroxyfluorene
Pentagon with -OH on top and part of two benzene rings on sides
*There is only one carbon not part of the benzene rings
Same as 9-fluorenol
Acetaminophen
OH-Ph-NH-C(=O)-CH3
directly across
Acetic Anhydride
CH3-C(=O)-O-C(=O)-CH3
Acetone
CH3-C(=O)-CH3
Amberlyst A-26 Resin
NH4+ OH-
Anhydrous Sodium Sulfate
Na2SO4
Benzil
Ph-C(=O)-C(=O)-Ph
Benzophenone
Ph-C(=O)-Ph
Biphenyl
Ph-Ph
Bromobenzene
Ph-Br
Chloroform D
DCCl3
Chromium Trioxide
Cr with three double bonds to oxygens (which each have two lone pairs)
(di)-Ethyl Ether
CH3-CH2-O-CH2-CH3
Ethyl Acetate
CH3-C(=O)-O-CH2-CH3
Isopropyl Alcohol
chain of 3 carbons, OH off of central
Methanol
CH3OH
Methylene Chloride
CH2Cl2
P-aminophenol
OH-Ph-NH2
directly opposite
Petroleum Ether
hexane
Phenacetin
CH3-CH2-O on one side of benzene ring opposite to NH-C(=O)-CH3
Pyridinium chlorochromate
Benzene ring with NH+ replacing one of the carbons
Cr double bonded to two O, single bonded to an O, and single bonded to Cl
Silica Gel
SiO2
Sodium Acetate
Na+ and negatively charged CH3-C(=O)-O
Sodium Borohydride
NaBH4
Sodium Dithionite
S connected to -O and =O that is connected to an identical S connected to -O and =O
Two Na+ ions
Sodium Methoxide
MeONa
Sodium Sulfite
O-S(=O)-O
each O on ends has negative charge, each bonded to a Na+
Na2SO3
Tetraphenylcyclopentadienone
pentagon with double bonds on sides and =O on top, with the four other carbons bonded to Ph
Triphenylmethanol
carbon connected to three Ph and a OH
Benzyl Group
Cyclohexene, then CH2, then attached to whatever the thing is
As polarity of the sample decreases, the distance from the TLC front _________
increases
As polarity of the solvent increases, the distance from the TLC front _________
increases
Rf =
distance traveled by spot / distance traveled by solvent
Theoretical Yield =
Grams * 1/MM * mol-reactant/mol-product * MM(product)
Percent Yield =
Actual / Theoretical * 100
Percent Error =
(theoretical - experimental)/(theoretical) * 100
Theoretical Maximum Solubility Recovery =
(ml water)(hot solubility in g/ml) minus (ml water)(cold solubility in g/ml)
all over grams and multiplied by 100
What is the equation for the reduction experiment? Include solvent
4 9-fluorenone + Sodium Borohydride (NaBH4) → 4 9-fluorenol
ethanol solvent
What is the mechanism for the reduction of aldehydes and ketones by hydride transfer? (on midterm)
BH4- attacks central carbon (due to + charge) pushing the electrons in the =O to be lone pairs
Water (or similar) then donates a H to the now negative O
End up replacing =O with -OH and -H
Fun Fact: What happens in the addition of HCl at the end of the reduction experiment?
Addition of HCl at the end of the reaction is reacting with excess NaBH4 and water to produce NaCl, H3BO3, and H2 gas
Fun Fact: What is the side reaction in the reduction experiment?
NaBH4 + ROH → NaB(OR)4 + H2
Fun Fact: What are the two layers created in the reduction experiment?
top is H3BO3, NaCl, HCl, and EtOH and bottom is reactant, product, EtOH
reactant/product are 9-one and 9-ol
How do you balance a half-cell reaction?
- Write reactant and product species that are changing as half cells (eliminate spectator ions).
- Balance all non H & O atoms with coefficients.
- Balance O atoms by adding H2O.
- Balance H atoms by adding H+.
- Balance charge by adding e-.
- Multiply balanced half cells by coefficients so that the e- lost in one equals e- gained in the other.
- Add the half cells and cancel common species.
What is the equation for the oxidation experiment? Include solvent
9-Fluorenol + CrO3 → 9-Fluorenone
toluene solvent
Primary Alcohols oxidize to _________
aldehydes, then carboxylic acids
Secondary Alcohols oxidize to __________
ketones
Tertiary Alcohols ______
do not oxidize
Fun Fact: How is the product isolated in the oxidation experiment?
Product is isolated by cold vacuum filtration with CH2Cl2 rinses, then dried with hair dryer
Define oxidation and reduction
Oxidation is increase O or decrease H, Reduction is decrease O or increase H
Fun Fact: What is the purpose of the resin used in the oxidation experiment?
Resin simplified product isolation and controls loss and possible contamination by Cr+6
What are the two equations in the grignard experiment? Include solvent(s)
Bromobenzene + Mg → Phenylmagnesium Bromide
Phenylmagnesium Bromide + Benzophenone → Triphenylmethanol
anhydrous ether is solvent for both
What is the general mechanism for a Grignard reaction with aldehydes/ketones?
grignard attacks central carbon (due to + charge), pushing electrons from double bond onto the oxygen
The addition of a hydrogen makes the negative oxygen an OH
Fun Fact: What does the HCl react with at the end of the grignard experiment?
At the end of the reaction, HCl is added and will react with excess Mg to produce H2
Fun Fact: Why does everything need to be dry in the grignard experiment?
Needs to be dry to avoid Grignard + Water → RH + Mg+2 + OH-
Why do we need to add the nonmetallic portion of the grignard reagent slowly?
Side reaction: RMgX + RX → RR + MgX2
This is why we need to add the bromobenzene slowly
Fun Fact: What is the side reaction with oxygen in the Grignard experiment?
React with oxygen to form ROOH, ROH, and HOMgX
Fun Fact: Reaction rates double with each _____*C increase
Reaction rates double with 10*C increase
Fun Fact: Problems with changing solvents include…(4 possible)
Problems with changing solvents: not soluble, side reactions at higher BP, difficult to remove, may not form complex
Fun Fact: The reaction in the grignard experiment can be initiated with ….. (6 possible)
Initiate by crushing/scratching Mg, adding I2, adding 1,2-dibromoethane, adding PhMgBr, ultrasound, heating
Fun Fact: The drying agent used in the grignard experiment is called ________ and will turn from _____ to ______
Drying agent is drierite (CaSO4), will turn from blue to pink
Fun Fact: The two layers created during the grignard workup are ______ and _______
Two layers during workup: top is Ph3COH and biphenyl and bottom is HCl, MgCl2
The product will be separated from its major contaminant, ________, during the grignard experiment by ________
Separate product and biphenyl by addition of hexane then vacuum filtration with cold hexane
What is the equation in the aldol experiment? Include solvent and catalyst.
Benzil + 1,3-diphenylacetone → tetraphenylcyclopentadienone
Solvent of EtOH, KOH catalyst
The mechanism for the self-condensation of acetophenone is _________________
*Was on midterm in two different forms
Acetophenone is acetone with one of the carbons replaced by Ph
OH- removes H on alpha carbon →
Negative alpha carbon attaches to carbonyl carbon of another acetophenone, pushing electrons from the double bond to oxygen onto the oxygen atom → addition of H2O adds a H to the negative oxygen and produces OH- → OH- removes H from the same alpha carbon, producing H2O and moving the electrons from the double bond to oxygen to form a new double bond with the alpha carbon → OH- on product leaves, moving the double bond over to between the alpha carbon and where it came from and electrons on the other oxygen move back down to re-form double bond
Product is Ph-C(=O)-CH2=CH(-CH3)-Ph
Fun Fact: A crossed aldol is a ____________. A common example of this is the reaction between aldehydes and ketones, which react to produce ___________ and then dehydrate to produce _________
Aldol condensations between different carbonyl reactants are called crossed or mixed reactions
R-C(-OH)H-CH2-C(=O)-R
R-CH=CH-C(=O)-R
Fun Fact: Chalones are ______________ and have a structure of __________
Chalcones are naturally occuring aldol proteins with a structure of Ph-C(=O)-CH=CH-Ph
Fun Fact: Dehydrated intermediates are common in aldol reactions under conditions of __________ and __________
RT and lower base concentration → partially dehydrated intermediates
In the recrystallization of p-aminophenol, what is the activated charcoal for?
remove color
In the recrystallization of p-aminophenol, what is the Na2SO3 for?
reducing agent
What is the equation for the first actual synthesis reaction we did? Include solvent.
P-aminophenol + Acetic Anhydride → Acetaminophen + Formic Acid
water solvent
What is the mechanism for the first actual synthesis reaction we did?
NH2 group on p-aminophenol attacks one of the =O carbons, which pushes the electrons from the double bond onto the O
the electrons from the bond the attacked carbon had to the central oxygen leave with the rest of the molecule, and the electrons on the =O come down to reform the bond
later, hydrogens are added to the part of the acetic anhydride that left, capping off the O on the end
For the first synthesis reaction we did, what is sodium dithionite and what is it for?
A common, water soluble reducing agent, that is frequently used in excess due to instability
decolorizing
What are star cracks on glassware from?
Star cracks in glassware are due to dinging them on a hard surface that is not quite hard enough to shatter the flask
What are powder funnels used for?
Powder funnels are used to avoid getting chemicals on the glass neck when transferring chemicals
_________ shaped stir bars are for round bottom flasks, while ________ bars are for __________
Egg shaped stir bars are designed for use in round bottom flasks, cylindrical bars are for flat bottom containers
For the first synthesis reaction we did, what was the solvent for the TLC?
TLC is with EtOAc (ethyl acetate)
H-NMR will give you the basic ____________________, uses ______ inches of sample, and a solvent (for the first synthesis reaction we did) of ______
H-NMR is for carbon skeleton
⅛” sample, solvent is d6-DMSO
What is the equation for the second (and last) actual reaction we did in the synthesis project? Include the solvent and catalyst.
Acetaminophen + Bromoethane → Phenacetin
NaOMe and EtOH are catalyst and solvent
For the second synthesis reaction we did, the purpose of the NaCl brine is to __________ and _________
Purpose of adding the NaCl brine is to prevent emulsions and force out H2O
For the second synthesis reaction we did, the purpose of the sodium sulfate is ____________
Purpose of adding the sodium sulfate to the extract is for use as a drying agent
High capacity and medium rate, forms sodium sulfate hydrate
For the second synthesis reaction we did, we did three extracts with ___________, a _________ wash, and dried with ____________
Three extracts with EtOAc, a NaCl wash, and rotovapping
For the second synthesis reaction we did, we used NaOMe to ____________
NaOMe is to form the conjugate base of the phenolic OH on acetaminophen (remove H)
NaOMe is catalyst
For the second synthesis reaction we did, NaOMe had a side reaction of __________ and a similar reaction of _________
NaOMe reacts with air/water to form NaOH and CO2 to form Na2CO3 (insoluble)
For the second synthesis reaction we did, the best leaving group was _____________, but ___________
Iodine is the best leaving group, but super expensive
For the second synthesis reaction we did, because ____________, we had to _________ our sep funnel during our extractions
Low BP solvents build up pressure, must vent sep funnel
What are emulsions? What are some ways of breaking them (4 possible)?
Emulsions: Suspension of droplets of one immiscible liquid in another
Breaking Emulsions → NaCl, stir with glass rod, allow to sit, centrifuge
Most organic solvents are ________ dense than water, halogenated solvents are _____________ dense
Most organic solvents are less dense than water, halogenated solvents are more dense
For the second synthesis reaction we did, the vacuum produced by the aspirator is limited by ____________________________________
The vacuum produced by an aspirator is limited by the vapor pressure of water at the boiling point of the water at a vacuum
For the second synthesis reaction we did, how did the pressure-temperature nomograph work?
Connect BP at 30*C and 30 Torr with BP at 760 Torr to
produce a horizontal line and find max vacuum produced by aspirator
In the Grignard experiment, there was a NaHCO3 wash. What was it for and what did it produce?
Wash with NaHCO3 is to remove residual HCl, will produce CO2 gas
NaHCO3 + HCl → NaCl + CO2 + H2O
Grignard Reagents (RMgX) can react with proton donors. What will they produce?
RMgX + Proton Donor → RH + MgX+ + Conjugate Base
