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Z - Chem 2229 (Organic Chemistry II Lab) > Final > Flashcards

Final Flashcards

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1
Q

air condenser

A

straight tube

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2
Q

casserole

A

clay cup on a stick

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3
Q

claisen adapter

A

tube that separates into two, U shaped

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4
Q

crucible tongs

A

go outward, for holding hot beakers and such

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5
Q

drying tube

A

tube that takes a hard right

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6
Q

Hickman still head

A

the tube that looks kinda squished down, tiny tube going into larger tube

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7
Q

jacked water condenser

A

two side ports, shell around tube

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8
Q

stirring rod with rubber policeman

A

glass rod, pointy rubber tip

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9
Q

sublimation adapter

A

short piece of glass with side port and slanted bottom

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10
Q

test tube clamp

A

holder part is little curved rectangles

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11
Q

thistle tube

A

looks like a vase on a stick

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12
Q

vacuum filter flask

A

large erlenmeyer with side port

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13
Q

Where are the safety showers? (2)

A

In both corners on the hallway side

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14
Q

Where are the fire blankets? (2)

A

In both corners on the hallway side, in the left corner the blanket is to the right of the cart

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15
Q

Where is the eyewash station? (1)

A

On the second station from the left

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16
Q

Where are the fire extinguishers? (3)

A

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)

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17
Q

1,3-diphenylacetone

A

Ph-CH2-C(=O)-CH2-Ph

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18
Q

9-Fluorenol

A

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

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19
Q

9-Fluorenone

A

Pentagon with =O on top and part of two benzene rings on sides

*There is only one carbon not part of the benzene rings

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20
Q

9-hydroxyfluorene

A

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

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21
Q

Acetaminophen

A

OH-Ph-NH-C(=O)-CH3

directly across

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22
Q

Acetic Anhydride

A

CH3-C(=O)-O-C(=O)-CH3

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23
Q

Acetone

A

CH3-C(=O)-CH3

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24
Q

Amberlyst A-26 Resin

A

NH4+ OH-

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25
Q

Anhydrous Sodium Sulfate

A

Na2SO4

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26
Q

Benzil

A

Ph-C(=O)-C(=O)-Ph

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27
Q

Benzophenone

A

Ph-C(=O)-Ph

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28
Q

Biphenyl

A

Ph-Ph

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29
Q

Bromobenzene

A

Ph-Br

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30
Q

Chloroform D

A

DCCl3

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31
Q

Chromium Trioxide

A

Cr with three double bonds to oxygens (which each have two lone pairs)

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32
Q

(di)-Ethyl Ether

A

CH3-CH2-O-CH2-CH3

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33
Q

Ethyl Acetate

A

CH3-C(=O)-O-CH2-CH3

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34
Q

Isopropyl Alcohol

A

chain of 3 carbons, OH off of central

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35
Q

Methanol

A

CH3OH

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36
Q

Methylene Chloride

A

CH2Cl2

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37
Q

P-aminophenol

A

OH-Ph-NH2

directly opposite

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38
Q

Petroleum Ether

A

hexane

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39
Q

Phenacetin

A

CH3-CH2-O on one side of benzene ring opposite to NH-C(=O)-CH3

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40
Q

Pyridinium chlorochromate

A

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

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41
Q

Silica Gel

A

SiO2

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42
Q

Sodium Acetate

A

Na+ and negatively charged CH3-C(=O)-O

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43
Q

Sodium Borohydride

A

NaBH4

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44
Q

Sodium Dithionite

A

S connected to -O and =O that is connected to an identical S connected to -O and =O

Two Na+ ions

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45
Q

Sodium Methoxide

A

MeONa

46
Q

Sodium Sulfite

A

O-S(=O)-O

each O on ends has negative charge, each bonded to a Na+

Na2SO3

47
Q

Tetraphenylcyclopentadienone

A

pentagon with double bonds on sides and =O on top, with the four other carbons bonded to Ph

48
Q

Triphenylmethanol

A

carbon connected to three Ph and a OH

49
Q

Benzyl Group

A

Cyclohexene, then CH2, then attached to whatever the thing is

50
Q

As polarity of the sample decreases, the distance from the TLC front _________

A

increases

51
Q

As polarity of the solvent increases, the distance from the TLC front _________

A

increases

52
Q

Rf =

A

distance traveled by spot / distance traveled by solvent

53
Q

Theoretical Yield =

A

Grams * 1/MM * mol-reactant/mol-product * MM(product)

54
Q

Percent Yield =

A

Actual / Theoretical * 100

55
Q

Percent Error =

A

(theoretical - experimental)/(theoretical) * 100

56
Q

Theoretical Maximum Solubility Recovery =

A

(ml water)(hot solubility in g/ml) minus (ml water)(cold solubility in g/ml)

all over grams and multiplied by 100

57
Q

What is the equation for the reduction experiment? Include solvent

A

4 9-fluorenone + Sodium Borohydride (NaBH4) → 4 9-fluorenol

ethanol solvent

58
Q

What is the mechanism for the reduction of aldehydes and ketones by hydride transfer? (on midterm)

A

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

59
Q

Fun Fact: What happens in the addition of HCl at the end of the reduction experiment?

A

Addition of HCl at the end of the reaction is reacting with excess NaBH4 and water to produce NaCl, H3BO3, and H2 gas

60
Q

Fun Fact: What is the side reaction in the reduction experiment?

A

NaBH4 + ROH → NaB(OR)4 + H2

61
Q

Fun Fact: What are the two layers created in the reduction experiment?

A

top is H3BO3, NaCl, HCl, and EtOH and bottom is reactant, product, EtOH

reactant/product are 9-one and 9-ol

62
Q

How do you balance a half-cell reaction?

A
  1. Write reactant and product species that are changing as half cells (eliminate spectator ions).
  2. Balance all non H & O atoms with coefficients.
  3. Balance O atoms by adding H2O.
  4. Balance H atoms by adding H+.
  5. Balance charge by adding e-.
  6. Multiply balanced half cells by coefficients so that the e- lost in one equals e- gained in the other.
  7. Add the half cells and cancel common species.
63
Q

What is the equation for the oxidation experiment? Include solvent

A

9-Fluorenol + CrO3 → 9-Fluorenone

toluene solvent

64
Q

Primary Alcohols oxidize to _________

A

aldehydes, then carboxylic acids

65
Q

Secondary Alcohols oxidize to __________

A

ketones

66
Q

Tertiary Alcohols ______

A

do not oxidize

67
Q

Fun Fact: How is the product isolated in the oxidation experiment?

A

Product is isolated by cold vacuum filtration with CH2Cl2 rinses, then dried with hair dryer

68
Q

Define oxidation and reduction

A

Oxidation is increase O or decrease H, Reduction is decrease O or increase H

69
Q

Fun Fact: What is the purpose of the resin used in the oxidation experiment?

A

Resin simplified product isolation and controls loss and possible contamination by Cr+6

70
Q

What are the two equations in the grignard experiment? Include solvent(s)

A

Bromobenzene + Mg → Phenylmagnesium Bromide

Phenylmagnesium Bromide + Benzophenone → Triphenylmethanol

anhydrous ether is solvent for both

71
Q

What is the general mechanism for a Grignard reaction with aldehydes/ketones?

A

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

72
Q

Fun Fact: What does the HCl react with at the end of the grignard experiment?

A

At the end of the reaction, HCl is added and will react with excess Mg to produce H2

73
Q

Fun Fact: Why does everything need to be dry in the grignard experiment?

A

Needs to be dry to avoid Grignard + Water → RH + Mg+2 + OH-

74
Q

Why do we need to add the nonmetallic portion of the grignard reagent slowly?

A

Side reaction: RMgX + RX → RR + MgX2

This is why we need to add the bromobenzene slowly

75
Q

Fun Fact: What is the side reaction with oxygen in the Grignard experiment?

A

React with oxygen to form ROOH, ROH, and HOMgX

76
Q

Fun Fact: Reaction rates double with each _____*C increase

A

Reaction rates double with 10*C increase

77
Q

Fun Fact: Problems with changing solvents include…(4 possible)

A

Problems with changing solvents: not soluble, side reactions at higher BP, difficult to remove, may not form complex

78
Q

Fun Fact: The reaction in the grignard experiment can be initiated with ….. (6 possible)

A

Initiate by crushing/scratching Mg, adding I2, adding 1,2-dibromoethane, adding PhMgBr, ultrasound, heating

79
Q

Fun Fact: The drying agent used in the grignard experiment is called ________ and will turn from _____ to ______

A

Drying agent is drierite (CaSO4), will turn from blue to pink

80
Q

Fun Fact: The two layers created during the grignard workup are ______ and _______

A

Two layers during workup: top is Ph3COH and biphenyl and bottom is HCl, MgCl2

81
Q

The product will be separated from its major contaminant, ________, during the grignard experiment by ________

A

Separate product and biphenyl by addition of hexane then vacuum filtration with cold hexane

82
Q

What is the equation in the aldol experiment? Include solvent and catalyst.

A

Benzil + 1,3-diphenylacetone → tetraphenylcyclopentadienone

Solvent of EtOH, KOH catalyst

83
Q

The mechanism for the self-condensation of acetophenone is _________________

*Was on midterm in two different forms

A

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

84
Q

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 _________

A

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

85
Q

Fun Fact: Chalones are ______________ and have a structure of __________

A

Chalcones are naturally occuring aldol proteins with a structure of Ph-C(=O)-CH=CH-Ph

86
Q

Fun Fact: Dehydrated intermediates are common in aldol reactions under conditions of __________ and __________

A

RT and lower base concentration → partially dehydrated intermediates

87
Q

In the recrystallization of p-aminophenol, what is the activated charcoal for?

A

remove color

88
Q

In the recrystallization of p-aminophenol, what is the Na2SO3 for?

A

reducing agent

89
Q

What is the equation for the first actual synthesis reaction we did? Include solvent.

A

P-aminophenol + Acetic Anhydride → Acetaminophen + Formic Acid

water solvent

90
Q

What is the mechanism for the first actual synthesis reaction we did?

A

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

91
Q

For the first synthesis reaction we did, what is sodium dithionite and what is it for?

A

A common, water soluble reducing agent, that is frequently used in excess due to instability

decolorizing

92
Q

What are star cracks on glassware from?

A

Star cracks in glassware are due to dinging them on a hard surface that is not quite hard enough to shatter the flask

93
Q

What are powder funnels used for?

A

Powder funnels are used to avoid getting chemicals on the glass neck when transferring chemicals

94
Q

_________ shaped stir bars are for round bottom flasks, while ________ bars are for __________

A

Egg shaped stir bars are designed for use in round bottom flasks, cylindrical bars are for flat bottom containers

95
Q

For the first synthesis reaction we did, what was the solvent for the TLC?

A

TLC is with EtOAc (ethyl acetate)

96
Q

H-NMR will give you the basic ____________________, uses ______ inches of sample, and a solvent (for the first synthesis reaction we did) of ______

A

H-NMR is for carbon skeleton

⅛” sample, solvent is d6-DMSO

97
Q

What is the equation for the second (and last) actual reaction we did in the synthesis project? Include the solvent and catalyst.

A

Acetaminophen + Bromoethane → Phenacetin

NaOMe and EtOH are catalyst and solvent

98
Q

For the second synthesis reaction we did, the purpose of the NaCl brine is to __________ and _________

A

Purpose of adding the NaCl brine is to prevent emulsions and force out H2O

99
Q

For the second synthesis reaction we did, the purpose of the sodium sulfate is ____________

A

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

100
Q

For the second synthesis reaction we did, we did three extracts with ___________, a _________ wash, and dried with ____________

A

Three extracts with EtOAc, a NaCl wash, and rotovapping

101
Q

For the second synthesis reaction we did, we used NaOMe to ____________

A

NaOMe is to form the conjugate base of the phenolic OH on acetaminophen (remove H)

NaOMe is catalyst

102
Q

For the second synthesis reaction we did, NaOMe had a side reaction of __________ and a similar reaction of _________

A

NaOMe reacts with air/water to form NaOH and CO2 to form Na2CO3 (insoluble)

103
Q

For the second synthesis reaction we did, the best leaving group was _____________, but ___________

A

Iodine is the best leaving group, but super expensive

104
Q

For the second synthesis reaction we did, because ____________, we had to _________ our sep funnel during our extractions

A

Low BP solvents build up pressure, must vent sep funnel

105
Q

What are emulsions? What are some ways of breaking them (4 possible)?

A

Emulsions: Suspension of droplets of one immiscible liquid in another

Breaking Emulsions → NaCl, stir with glass rod, allow to sit, centrifuge

106
Q

Most organic solvents are ________ dense than water, halogenated solvents are _____________ dense

A

Most organic solvents are less dense than water, halogenated solvents are more dense

107
Q

For the second synthesis reaction we did, the vacuum produced by the aspirator is limited by ____________________________________

A

The vacuum produced by an aspirator is limited by the vapor pressure of water at the boiling point of the water at a vacuum

108
Q

For the second synthesis reaction we did, how did the pressure-temperature nomograph work?

A

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

109
Q

In the Grignard experiment, there was a NaHCO3 wash. What was it for and what did it produce?

A

Wash with NaHCO3 is to remove residual HCl, will produce CO2 gas

NaHCO3 + HCl → NaCl + CO2 + H2O

110
Q

Grignard Reagents (RMgX) can react with proton donors. What will they produce?

A

RMgX + Proton Donor → RH + MgX+ + Conjugate Base

Z - Chem 2229 (Organic Chemistry II Lab) (8 decks)

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