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lab final Flashcards

1
Q

oxidation of unknown alcohol:
starting material

A

unknown secondary alcohol

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2
Q

oxidation of unknown alcohol:
oxidizing agent

A

sodium hypochlorite (NaOCl) —> hypochlorous acid (HOCl)

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3
Q

oxidation of unknown alcohol:
solvent

A

acetic acid (CH3CO2H)

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4
Q

oxidation of unknown alcohol:
product

A

ketone

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5
Q

oxidation of unknown alcohol:
line reaction regents

A

5% NaOCl, CH3CO2H 0 C

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6
Q

oxidation of unknown alcohol:
testing for excess hypochlorite

A

if the KI-starch paper turned blue when coming into contact with the reaction solution, there was excess hypochlorite in solution = move onto quenching
if it remained white, add extra NaOCl until the paper turned blue

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7
Q

oxidation of unknown alcohol:
reaction quenching agent

A

sodium bisulfite used to quench excess hypochlorite remaining after the reaction has gone to completion

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8
Q

oxidation of unknown alcohol:
reaction quenching and KI-starch paper

A

used to check the progress of the quenching process
checking to ensure the paper remained white instead of turning blue

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9
Q

what is quenching?

A

forcing any residual oxidizer to react, stopping the reaction

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10
Q

oxidation of unknown alcohol:
basification reagent

A

6M sodium hydroxide

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11
Q

oxidation of unknown alcohol:
basification process

A

after the reaction was complete, 6M sodium hydroxide was added to achieve a basic solution
the base neutralized the residual acetic acid (forming acetate) allowed it to be water soluble while the product remained un-ionized

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12
Q

oxidation of unknown alcohol:
extraction reagent used

A

methylene chloride

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13
Q

oxidation of unknown alcohol:
extraction process

A

methylene chloride (denser than water) was used to extract the product into the organic layer (bottom) using a separatory funnel
organic layer was collected and washed with deionized water and brine (to remove excess water)

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14
Q

oxidation of unknown alcohol:
drying agent and how it was removed

A

organic layer dried with magnesium sulfate (MgSO4) and removed via gravity filtration

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15
Q

oxidation of unknown alcohol:
reagent in line reaction using common names

A

bleach, acetic acid

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16
Q

conversion of carvone to carvacrol:
starting material

A

(R)-(-) carvone

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17
Q

conversion of carvone to carvacrol:
catalyst/solvent

A

6M H2SO4

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18
Q

conversion of carvone to carvacrol:
product

A

carvacrol

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19
Q

conversion of carvone to carvacrol:
what does the reaction do?

A

converts a chiral compound to an achiral compound through an acid-catalyzed elimination

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20
Q

conversion of carvone to carvacrol:
reagents on line reaction

A

H2SO4, heat

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21
Q

conversion of carvone to carvacrol:
what is the reaction driven by?

A

aromaticity

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22
Q

what is reflux?

A

boiling a reaction without losing solvent

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23
Q

conversion of carvone to carvacrol:
extraction reagent used

A

after reflux, the product was transferred to a separatory funnel and extracted into diethyl ether and washed with brine

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24
Q

conversion of carvone to carvacrol:
basification reagent

A

ether extract was washed with sodium bicarbonate (NaHCO3) to neutralize the acid

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25
Q

conversion of carvone to carvacrol:
drying agent and removal

A

ether dried with sodium sulfate (Na2SO4) and removed via suction filtration

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26
Q

conversion of carvone to carvacrol:
ether removal

A

evaporation

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27
Q

Williamson ether synthesis (microwave edition):
occurs under what conditions?
what type of alkyl halides are used?
what kind of reaction?

A

basic
primary
SN2

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28
Q

Williamson ether synthesis (microwave edition):
starting materials

A

4-bromophenol and unknown aldehyde

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29
Q

Williamson ether synthesis (microwave edition):
catalysts

A

tetra-N-butylammonium bromide (TBAB) = phase transfer catalyst
KOH = base catalyst

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30
Q

Williamson ether synthesis (microwave edition):
solvent

A

water

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31
Q

Williamson ether synthesis (microwave edition):
product

A

ether

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32
Q

Williamson ether synthesis (microwave edition):
how does TBAB work as a phase-transfer catalyst?

A

helps ions cross between the organic and aqueous phase

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33
Q

what is microwave reflux?

A

a technique that heats reactions without losing solvent
speed up reaction times by holding reaction at constant temperature and pressure

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34
Q

Williamson ether synthesis (microwave edition):
extraction reagents used

A

diethyl ether and water

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35
Q

Williamson ether synthesis (microwave edition):
basification reagent

A

potassium hydroxide

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36
Q

Williamson ether synthesis (microwave edition):
drying reagent and removal

A

sodium sulfate and removed via gravity filtration

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37
Q

Williamson ether synthesis (microwave edition):
purification method

A

gas chromatography

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38
Q

GC separates components of a mixture to what scale?

A

milligram-to-gram

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39
Q

GC mobile phase
polarity?

A

methylene chloride (DCM)
less polar

40
Q

GC stationary phase
polarity?

A

silica gel
more polar

41
Q

Williamson ether synthesis (microwave edition):
mobile phase

A

product of this reaction will remain in the mobile phase because it is less polar than the highly polar stationary phase

42
Q

Williamson ether synthesis (microwave edition):
stationary phase

A

residual polar impurities from this reaction bind to silica gel and do not get collected

43
Q

Williamson ether synthesis (microwave edition):
removal of excess solvent

A

hot plate with a snorkel

44
Q

TLC stationary phase
polarity?

A

silica gel
polar compounds bind to silica gel and do not migrate up the plate

45
Q

TLC mobile phase
polarity?

A

methylene chloride
less polar compounds remain in the mobile phase and migrate up the plate with the solvent front

46
Q

TLC Rf calculation

A

distance from origin to spot/distance from origin to solvent front

47
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
acidic cleavage vs basic cleavage
stereochemistry

A

acid: nucleophile attacks more sub side
base: nucleophile attacks less sub side
stereochem: anti addition

48
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
starting material

A

1,2-epoxyhexane

49
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
acid catalyst
base catalyst

A

acid: sulfuric acid (H2SO4)
base: sodium methoxide (NaOCH3)

50
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
solvent

A

methanol (CH3OH)

51
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
acid reagents on line reaction
base reagents on line reaction

A

acid:
H2SO4, methanol

base:
1. NaOCH3, methanol
2. NH4Cl

52
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
acidic: washed with ___ to neutralize
basic: washed with ___ to neutralize

A

acid: saturated sodium bicarbonate
base: saturated ammonium chloride

53
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
drying agent and removed via

A

magnesium sulfate removed via decating

54
Q

acid v.s base nucleophilic ring opening of 1,2-epoxyhexane:
removal of excess ether

A

rotary evaporator

55
Q

GC mixture is separated based on each component’s affinity for the ___phase vs the ___ phase
each component will exit the column ____

A

non-polar stationary phase vs the inert gas mobile phase
at different retention times

56
Q

GC % of each component calculation

A

(A1/ (A1 + A2 + A3 )) x 100

57
Q

Fischer esterification (microwave edition):
starting materials

A

acetic acid and unknown primary alcohol

58
Q

Fischer esterification (microwave edition):
catalyst

A

sulfuric acid (H2SO4)

59
Q

Fischer esterification (microwave edition):
solvent

A

acetic acid (CH3CO2H)

60
Q

Fischer esterification (microwave edition):
products

A

ester and H20

61
Q

Fischer esterification (microwave edition):
how to drive the reaction’s equilibrium toward the formation of the products

A

Le Chatlier’s principle:
-increase concentration of reactants
-decrease concentration of products (remove water easiest)

62
Q

Fischer esterification (microwave edition):
extraction reagents

A

washed with water and then with 5% sodium bicarbonate solution

63
Q

Fischer esterification (microwave edition):
basification reagent
formed what?

A

sodium bicarbonate to neutralize the organic layer resulting in the formation of CO2 that bubbled out of solution
then final brine wash

64
Q

Fischer esterification (microwave edition):
drying agent and removal

A

sodium sulfate (Na2SO4) removed via decanting

65
Q

amide synthesis:
starting materials

A

acetic anhydride and unknown primary amine

66
Q

amide synthesis:
catalyst
provides what?

A

aluminum oxide (Al2O3)
a basic polar surface for the reaction to take place on while also neutralizing acetic acid byproduct as it forms

67
Q

amide synthesis:
solvent

A

acetic anhydride ((CH3CO)2O)

68
Q

amide synthesis:
products

A

amide and acetate

69
Q

amide synthesis:
line reaction reagent

A

solid Al2O3

70
Q

amide synthesis:
using aluminum oxide allows for?

A

admiration of a carboxylic acid in high yields without having to use an acid halide

71
Q

amide synthesis:
isolation method

A

solid/liquid extraction

72
Q

amide synthesis:
extraction reagent

A

ethyl acetate

73
Q

reduction of an unknown aldehyde/ketone (microwave edition):
starting material

A

unknown ketone/aldehyde

74
Q

reduction of an unknown aldehyde/ketone (microwave edition):
reducing agent
also acts as?

A

sodium borohydride (NaBH4)
nucleophile

75
Q

reduction of an unknown aldehyde/ketone (microwave edition):
solvent

A

95% ethanol

76
Q

reduction of an unknown aldehyde/ketone (microwave edition):
product

A

primary or secondary alcohol

77
Q

reduction of an unknown aldehyde/ketone (microwave edition):
line reaction reagents

A
  1. NaBH4, 95% ethanol
  2. H20
78
Q

reduction of an unknown aldehyde/ketone (microwave edition):
extraction regent used

A

methylene chloride

79
Q

reduction of an unknown aldehyde/ketone (microwave edition):
drying agent and removal

A

magnesium sulfate removed via filtration

80
Q

Wittig Reaction:
starting materials

A

benzyltriphenylphosphonium chloride (slide) and 9-anthraldehyde

81
Q

Wittig Reaction:
solvent

A

methylene chloride (CH2Cl2)

82
Q

Wittig Reaction:
products

A

9-(2-phenylethenyl)anthracene and O=PPh3

83
Q

Wittig Reaction:
line reaction reagents

A

NaOH, CH2Cl2
then
CH2Cl2

84
Q

Wittig Reaction:
basification reagent

A

sodium hydroxide added dropwise resulting in formation of ylide

85
Q

Wittig Reaction:
reaction mixture is non-homogenous as the aldehyde is ____ and the ylide is ___

A

hydrophobic, hydrophilic

86
Q

Wittig Reaction:
-what is major product?
-what type of alkyl halides are best for making ylides?

A

-E
-primary

87
Q

Wittig Reaction:
drying agent and removal

A

calcium chloride (CaCl2) removed via decanting

88
Q

Wittig Reaction:
simple distillation did what?

A

removed methylene chloride

89
Q

Wittig Reaction:
product was purified how?

A

recrystallization

90
Q

aldol condensation:
starting materials

A

acetone (Nu-) and 2 eq unknown aldehyde (E+)

91
Q

aldol condensation:
solvent

A

95% ethanol

92
Q

aldol condensation:
product (prefers what stereochem?)

A

a/B-unsaturated ketone (prefers E)

93
Q

aldol condensation:
how is sodium hydroxide added?

94
Q

aldol condensation:
line reaction reagents

A

aq NaOH, 95% ethanol

95
Q

aldol condensation:
isolation methods

A

crystallization and recrystallization

96
Q

aldol condensation:
crystals washed with what?

A

sodium hydroxide to neutralize

97
Q

aldol condensation:
recrystallization used for what?

A

purification

o chem 2 (5 decks)

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