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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
conversion of carvone to carvacrol: drying agent and removal
ether dried with sodium sulfate (Na2SO4) and removed via suction filtration
26
conversion of carvone to carvacrol: ether removal
evaporation
27
Williamson ether synthesis (microwave edition): occurs under what conditions? what type of alkyl halides are used? what kind of reaction?
basic primary SN2
28
Williamson ether synthesis (microwave edition): starting materials
4-bromophenol and unknown aldehyde
29
Williamson ether synthesis (microwave edition): catalysts
tetra-N-butylammonium bromide (TBAB) = phase transfer catalyst KOH = base catalyst
30
Williamson ether synthesis (microwave edition): solvent
water
31
Williamson ether synthesis (microwave edition): product
ether
32
Williamson ether synthesis (microwave edition): how does TBAB work as a phase-transfer catalyst?
helps ions cross between the organic and aqueous phase
33
what is microwave reflux?
a technique that heats reactions without losing solvent speed up reaction times by holding reaction at constant temperature and pressure
34
Williamson ether synthesis (microwave edition): extraction reagents used
diethyl ether and water
35
Williamson ether synthesis (microwave edition): basification reagent
potassium hydroxide
36
Williamson ether synthesis (microwave edition): drying reagent and removal
sodium sulfate and removed via gravity filtration
37
Williamson ether synthesis (microwave edition): purification method
gas chromatography
38
GC separates components of a mixture to what scale?
milligram-to-gram
39
GC mobile phase polarity?
methylene chloride (DCM) less polar
40
GC stationary phase polarity?
silica gel more polar
41
Williamson ether synthesis (microwave edition): mobile phase
product of this reaction will remain in the mobile phase because it is less polar than the highly polar stationary phase
42
Williamson ether synthesis (microwave edition): stationary phase
residual polar impurities from this reaction bind to silica gel and do not get collected
43
Williamson ether synthesis (microwave edition): removal of excess solvent
hot plate with a snorkel
44
TLC stationary phase polarity?
silica gel polar compounds bind to silica gel and do not migrate up the plate
45
TLC mobile phase polarity?
methylene chloride less polar compounds remain in the mobile phase and migrate up the plate with the solvent front
46
TLC Rf calculation
distance from origin to spot/distance from origin to solvent front
47
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: acidic cleavage vs basic cleavage stereochemistry
acid: nucleophile attacks more sub side base: nucleophile attacks less sub side stereochem: anti addition
48
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: starting material
1,2-epoxyhexane
49
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: acid catalyst base catalyst
acid: sulfuric acid (H2SO4) base: sodium methoxide (NaOCH3)
50
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: solvent
methanol (CH3OH)
51
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: acid reagents on line reaction base reagents on line reaction
acid: H2SO4, methanol base: 1. NaOCH3, methanol 2. NH4Cl
52
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: acidic: washed with ___ to neutralize basic: washed with ___ to neutralize
acid: saturated sodium bicarbonate base: saturated ammonium chloride
53
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: drying agent and removed via
magnesium sulfate removed via decating
54
acid v.s base nucleophilic ring opening of 1,2-epoxyhexane: removal of excess ether
rotary evaporator
55
GC mixture is separated based on each component's affinity for the ___phase vs the ___ phase each component will exit the column ____
non-polar stationary phase vs the inert gas mobile phase at different retention times
56
GC % of each component calculation
(A1/ (A1 + A2 + A3 )) x 100
57
Fischer esterification (microwave edition): starting materials
acetic acid and unknown primary alcohol
58
Fischer esterification (microwave edition): catalyst
sulfuric acid (H2SO4)
59
Fischer esterification (microwave edition): solvent
acetic acid (CH3CO2H)
60
Fischer esterification (microwave edition): products
ester and H20
61
Fischer esterification (microwave edition): how to drive the reaction's equilibrium toward the formation of the products
Le Chatlier's principle: -increase concentration of reactants -decrease concentration of products (remove water easiest)
62
Fischer esterification (microwave edition): extraction reagents
washed with water and then with 5% sodium bicarbonate solution
63
Fischer esterification (microwave edition): basification reagent formed what?
sodium bicarbonate to neutralize the organic layer resulting in the formation of CO2 that bubbled out of solution then final brine wash
64
Fischer esterification (microwave edition): drying agent and removal
sodium sulfate (Na2SO4) removed via decanting
65
amide synthesis: starting materials
acetic anhydride and unknown primary amine
66
amide synthesis: catalyst provides what?
aluminum oxide (Al2O3) a basic polar surface for the reaction to take place on while also neutralizing acetic acid byproduct as it forms
67
amide synthesis: solvent
acetic anhydride ((CH3CO)2O)
68
amide synthesis: products
amide and acetate
69
amide synthesis: line reaction reagent
solid Al2O3
70
amide synthesis: using aluminum oxide allows for?
admiration of a carboxylic acid in high yields without having to use an acid halide
71
amide synthesis: isolation method
solid/liquid extraction
72
amide synthesis: extraction reagent
ethyl acetate
73
reduction of an unknown aldehyde/ketone (microwave edition): starting material
unknown ketone/aldehyde
74
reduction of an unknown aldehyde/ketone (microwave edition): reducing agent also acts as?
sodium borohydride (NaBH4) nucleophile
75
reduction of an unknown aldehyde/ketone (microwave edition): solvent
95% ethanol
76
reduction of an unknown aldehyde/ketone (microwave edition): product
primary or secondary alcohol
77
reduction of an unknown aldehyde/ketone (microwave edition): line reaction reagents
1. NaBH4, 95% ethanol 2. H20
78
reduction of an unknown aldehyde/ketone (microwave edition): extraction regent used
methylene chloride
79
reduction of an unknown aldehyde/ketone (microwave edition): drying agent and removal
magnesium sulfate removed via filtration
80
Wittig Reaction: starting materials
benzyltriphenylphosphonium chloride (slide) and 9-anthraldehyde
81
Wittig Reaction: solvent
methylene chloride (CH2Cl2)
82
Wittig Reaction: products
9-(2-phenylethenyl)anthracene and O=PPh3
83
Wittig Reaction: line reaction reagents
NaOH, CH2Cl2 then CH2Cl2
84
Wittig Reaction: basification reagent
sodium hydroxide added dropwise resulting in formation of ylide
85
Wittig Reaction: reaction mixture is non-homogenous as the aldehyde is ____ and the ylide is ___
hydrophobic, hydrophilic
86
Wittig Reaction: -what is major product? -what type of alkyl halides are best for making ylides?
-E -primary
87
Wittig Reaction: drying agent and removal
calcium chloride (CaCl2) removed via decanting
88
Wittig Reaction: simple distillation did what?
removed methylene chloride
89
Wittig Reaction: product was purified how?
recrystallization
90
aldol condensation: starting materials
acetone (Nu-) and 2 eq unknown aldehyde (E+)
91
aldol condensation: solvent
95% ethanol
92
aldol condensation: product (prefers what stereochem?)
a/B-unsaturated ketone (prefers E)
93
aldol condensation: how is sodium hydroxide added?
dropwise
94
aldol condensation: line reaction reagents
aq NaOH, 95% ethanol
95
aldol condensation: isolation methods
crystallization and recrystallization
96
aldol condensation: crystals washed with what?
sodium hydroxide to neutralize
97
aldol condensation: recrystallization used for what?
purification

o chem 2 (5 decks)

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