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CHEM 2212L Final > Reagents COPY > Flashcards

Reagents COPY Flashcards

1
Q

What is NaOCl

A

mild oxidizing agent (forms ketone)

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2
Q

in lab 1 (oxidation of unknown OH) , NaOcl and acetic acid will form __ which is a ____ ____

A

hypochlorous acid, oxidizing agent

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3
Q

HOCl aka

A

hypochlorous acid

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4
Q

in lab 1(oxidation of unknown OH) , if the KI paper was blue then __ was present

A

excess hypochlorous acid

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5
Q

in lab 1(oxidation of unknown OH) , what was the quenching reagent

A

sodium bisulfate

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6
Q

NaHSO3 aka

A

sodium bisulfate (quenching reagent)

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7
Q

in lab 1(oxidation of unknown OH) , how can you tell if the reaction was quenched

A

the KI starch paper was white

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8
Q

what is quenching

A

forcing any residual oxidizer to react, will stop a reaction

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9
Q

in lab 1(oxidation of unknown OH) , how was the product extracted

A

with methylene chloride

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10
Q

is methylene chloride more or less dense than water and found on bottom or top

A

more dense, found on bottom

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11
Q

in lab 1(oxidation of unknown OH) , after the reaction was quenched, how was it baseified

A

using NaOH (allowed to be water soluble and keep product unionized)

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12
Q

washing with brine does what

A

remove excess water

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13
Q

in lab 1(oxidation of unknown OH) , the drying agent was

A

magnesium sulfate

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14
Q

MgSO4

A

magnesium sulfate (drying agent)

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15
Q

in lab 1(oxidation of unknown OH) , oxidation of an unknown alcohol, what was important for IR/HNMR

A

OH stretch changed to C=O stretch.

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16
Q

what are the three main steps for almost every extraction

A
  1. extract into the solvent
  2. dry (decant, gravity filter)
  3. rotovap
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17
Q

in lab 1(oxidation of unknown OH) , what was the solvent

A

Acetic acid

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18
Q

CH3COOH aka

A

acetic acid

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19
Q

in lab 2 (carvone to carvacrol) , a ___ compound was changed to ___ using ____

A

chiral to achiral, acid catalyzed elimination

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20
Q

in lab 2 (carvone to carvacrol) , what was the catalyst AND solvent

A

sulfuric acid

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21
Q

H2SO4

A

sulfuric acid

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22
Q

can a 3° alcohol be oxidized?

A

no

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23
Q

in lab 2 (carvone to carvacrol) , what are the steps of the mechanism

A

tautomerization to form enos, carbocation rearrangement (aromatic driven)

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24
Q

in lab 2 (carvone to carvacrol) , what was the product extracted into

A

diethyl ether

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25
Q

C4H10O

A

diethyl ether

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26
Q

in lab 2 (carvone to carvacrol) , what was used to baseify the reaction

A

sodium bicarbonate

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27
Q

NaHCO3

A

sodium bicarbonate

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28
Q

in lab 2 (carvone to carvacrol) , why was sodium bicarbonate used

A

to neutralize the acid

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29
Q

in lab 2 (carvone to carvacrol) , the drying agent was

A

sodium sulfate

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30
Q

Na2SO4

A

sodium sulfate

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31
Q

in lab 2 (carvone to carvacrol) , the important part of charcterization was the ___ and

A

C=O changing to OH stretch and new aromatic peaks

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32
Q

in lab 3(Williamson ether), what was combined to form an ether

A

alcohol and alkyl halide

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33
Q

what did the microwave do for all the experiments it was used in

A

sped up the reaction due to constant temp and pressure without losing solvent

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34
Q

in lab 3, what kind of mechanism happened (Williamson ether)

A

SN2

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35
Q

in lab3, what were the catlyst

A

KOH and TBAB

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36
Q

what kind of catalyst is TBAB

A

phase transfer

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37
Q

what does TBAB mean

A

tetra-n-butylammonium bromide

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38
Q

in lab 2 (carvone to carvacrol) , what proceed was used

A

reflux

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39
Q

in lab 3 (Williamson ether) , what was the product extracted into

A

diethyl ether

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40
Q

in lab 3 (Williamson ether) , what wash was used and why

A

KOH (potassium hydroxide) to remove impurities

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41
Q

in lab 3 (Williamson ether) , what was used to dry the solution

A

sodium sulfate

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42
Q

in lab 3 (Williamson ether) , how was the product purified

A

column chromatography

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43
Q

what is column chromatography

A

3D qualitative test w mobile (DCM, less polar) and stationary phase (silicia gel, polar)

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44
Q

in column chromatography where did the product stay

A

in the mobile (DCM, less polar phase)

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45
Q

in lab 3 (Williamson ether) characterization, what was important

A

no more OH stitch, C-O-C ether stretch new

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46
Q

how do you calculate retention factor

A

Rf=distance origin to spot/ distance origin to solvent front

47
Q

in lab 4, (acid-base ring opening)nucleophile in acid attacks _____ sub and base ____ sub

A

more, least

48
Q

in lab 4,(acid-base ring opening) the reaction always gives ____ products

A

anti

49
Q

in lab 4, (acid-base ring opening) what was the catalyst (acid)

A

H2SO4

50
Q

in lab 4, (acid-base ring opening) what was the solvent, (acid)

A

methanol

51
Q

in lab 4, (acid-base ring opening) in the basic experiment, what was special about the second step of the reaction

A

NH4Cl ammonium chloride was needed for a workup (if H+ was used then the ether would cleave in acidic)

52
Q

in lab 4, (acid-base ring opening) what was the catalyst (base)

A

sodium methoxide NaOCH3

53
Q

in lab 4, (acid-base ring opening) how was procedure done

A

liquid liquid extraction

54
Q

in lab 4 (acid-base ring opening) acidic cond. what was used to wash

A

sodium bicarbonate (neutralize)

55
Q

in lab 4 (acid-base ring opening) basic cond. what was used to wash

A

ammonium chloride (neutralize)

56
Q

in lab 4, (acid-base ring opening) what was the drying agent

A

magnesium sulfate

57
Q

what does a longer retention time mean?

A

it is more polar

58
Q

what was used for characterization in lab 4 (acid-base ring opening)

A

gas chromatography

59
Q

how do you find the % product given gas chromatography?

A

% product = A1/A1+A2 (A=area)

60
Q

in lab 5, (fischer esterification) an ester was made from ___ and ___

A

alcohol and carboxylic acid

61
Q

in lab 5 what was the catalyst (fischer esterification)

A

sulfuric acid

62
Q

in lab 5 (fischer esterification) what was the solvent

A

acetic acid

63
Q

in lab 5 (fischer esterification) why is the unknown alcohol in excess?

A

to drive reaction toward product (le chat)

64
Q

what is special about fischer reactions

A

microscope reversibility

65
Q

what produce was used in lab 5 (fischer esterification)

A

microwave, liquid/liquid

66
Q

in lab 5 (fischer esterification) , the product separated when ___ was added

A

water

67
Q

in lab 5 (fischer esterification) , what was used to wash the product

A

sodium bicarbonate (NaHCO3) (used to neutralize)

68
Q

what caused the bubbles to form in lab 5 (fischer esterification) and what are the bubbles

A

sodium bicarbonate cause them and it was CO2

69
Q

what was the drying agent in lab 5 (fischer esterification)

A

sodium sulfate

70
Q

what was notable about characterization in lab 5 (fischer esterification)

A

COOH change to COC

71
Q

in lab 6 (amide synthesis), what was used to form amide

A

reactive carboxylic acid (acetic anhydride) and amine

72
Q

in lab 6 (amide synthesis), why was acid halide not used

A

its moisture reactive

73
Q

in lab 6 (amide synthesis), why was Al2O3 used

A

allowed to not use AH and still get amide

74
Q

Al2O3 is

A

aluminum oxide

75
Q

in lab 6 (amide synthesis), the catalyst is

A

aluminum oxide

76
Q

in lab 6 (amide synthesis), the solvent is

A

acetic anhydride

77
Q

in lab 6 (amide synthesis), the product was extracted using

A

ethyl acetate

78
Q

in lab 6 (amide synthesis), what was important about characterization

A

C-O-C stretch changed to N-H

79
Q

what changes the melting point and how

A

impurities, broaden and lower the range

80
Q

in lab 7, (reduction of ketone/aldehyde), what was the reducing agent

A

sodium borohyride NaBH4

81
Q

NaBH4 aka and is a ___

A

sodium borohydride, mild reducing agent

82
Q

in lab 7, (reduction of ketone/aldehyde), the solvent was

A

ethanol

83
Q

in lab 7, (reduction of ketone/aldehyde), what was used to extract product

A

methylene chloride (bottom of funnel)

84
Q

in lab 7, (reduction of ketone/aldehyde), what was the drying agent

A

magnesium sulfate

85
Q

in lab 7, (reduction of ketone/aldehyde), what was important about characterization

A

C=O to OH stretch

86
Q

in lab 8 (wittig reaction), what forms

A

c=c

87
Q

in lab 8 (wittig reaction), what was the solvent

A

methylene chloride

88
Q

in lab 8 (wittig reaction), what was used for baseification

A

sodium hydroxide NaOH

89
Q

in lab 8 (wittig reaction), the aldehyde is __ and the pph3 is ___

A

hydrophobic, hydrophilic

90
Q

in lab 8 (wittig reaction), the ___ product will be formed

A

Z product

91
Q

in lab 8 (wittig reaction), to make a ylide it is a ___ reaction

A

SN2

92
Q

in lab 8 (wittig reaction), what was used for procedure

A

liquid/liquid, simple distillation

93
Q

what is simple distillation

A

used when there is >100°C difference in boiling points to remove miscible liquid (DCM)

94
Q

in lab 8 (wittig reaction), what was the final step of procedure

A

recrystallization with 1-propanol

95
Q

in lab 8 (wittig reaction), what was important about characterization

A

C=O to C=C stretch

96
Q

in lab 9 (aldol condensation), what was formed

A

alpha-beta unsaturated compound

97
Q

in lab 9 (aldol condensation), why was that type of product formed

A

conjugation driven

98
Q

in lab 9 (aldol condensation), what was the solvent

A

ethanol

99
Q

in lab 9 (aldol condensation), what was added dropwise

A

sodium hydroxide

100
Q

in lab 9 (aldol condensation), what is formed in the reaction mechanism as an intermediate

A

enolate

101
Q

in lab 9 (aldol condensation), when crystals were collected what were they washed with and why

A

water, neutralize excess sodium hydroxide

102
Q

in lab 9 (aldol condensation), how did you check for neutralization

A

pH strip

103
Q

in lab 9 (aldol condensation), what was final step of procedure

A

recrystallization with ethanol

104
Q

in lab 9 (aldol condensation), what was notable about characterization

A

sp3 CH changed to sp2 CH

105
Q

in lab 10 (friedel-crafts alkylation), what was solvent

A

acetic acid

106
Q

in lab 10 (friedel-crafts alkylation), what was catalyst

A

sulfuric acid

107
Q

in lab 10 (friedel-crafts alkylation), what type of product formed

A

dialkylated ortho compound

108
Q

in lab 10 (friedel-crafts alkylation), where was the electrophile generated

A

in situ (in solution)

109
Q

in lab 10 (friedel-crafts alkylation), how does benzene reform aromaticity

A

E1 elim.

110
Q

in lab 10 (friedel-crafts alkylation), what was used to quench

A

ice cold water

111
Q

in lab 10 (friedel-crafts alkylation), what was used for recrystallization

A

methanol

112
Q

in lab 10 (friedel-crafts alkylation), what was important about characterization

A

arene peaks in product, double the signals hnmr

113
Q
A

CHEM 2212L Final (3 decks)

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