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Organic Chem 2 > Lab Exam Final > Flashcards

Lab Exam Final Flashcards

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1
Q

What are the correct steps for washing glassware

A

1- acetone
2- soap and water
3- acetone

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2
Q

How to dry glassware standard

A

on papertowel to air dry

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3
Q

How to dry glassware for moisture sensitive reactions

A

flame drying

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4
Q

first number pf taper glassware

A

diameter of top joint

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5
Q

second number of tapered glassware

A

inner length of the joint

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6
Q

weighing solids

A

weigh paper on scale, tare, add and remove solid till amount is reached

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7
Q

hot water baths

A

used for heating low boiling liquids

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8
Q

How to hold a pipette

A

vertically to prevent spilling and filling the bulb

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9
Q

How does 250 mg look on a gram scale

A

0.250 g

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10
Q

How do you weigh a liquid

A

Use the mass difference

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11
Q

How to prepare paper for gravity filtration

A

Flute it

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12
Q

What goes on filter flask for vacuum filtration

A

Büchner funnel and adapter

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13
Q

What is the purpose of vacuum filtration

A

To remove liquid mixture from final product/ solid

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14
Q

Where to dispose of organic solvents

A

organic liquid waste

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15
Q

Where to dispose of aqueous solvents go

A

aqueous liquid waste

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16
Q

where does paper go

A

contaminated paper wsate

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17
Q

where does glass go

A

yellow broken glass bin

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18
Q

where do tlc plates go

A

TLC waste bin

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19
Q

where do solids and boiling stones go

A

solid waste bin

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20
Q

where does clean acetone rinse go

A

acetone recovery

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21
Q

where does silica go

A

silica waste bin

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22
Q

what goes on filter flask for reduced pressure evaporation

A

cork or Buchner funnel filter paper and adaptor

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23
Q

what is the purpose of reduced pressure evaporation

A

remove liquid from solid, remove the solvent from sample or concentrate it

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24
Q

miscible

A

describes two liquids that are soluble in each other

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25
Q

density of water

A

1 g/mL

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26
Q

what two solvents are denser than water

A

DCM and chloroform

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27
Q

what is the purpose of a variac

A

the heating mantel can not be connected directly to the outlet or else it will become too hot and will easily vaporize contents of flask,variac which runs full power put cycles on and off prevents from happening

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28
Q

how to adjust setup if liquid is boiling too much or bumping

A

lower the lab jack & mantle, and can turn down variac

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29
Q

purpose of stir bars

A

stirring and preventing bumping

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30
Q

reflux set up

A

lack jack, mantle, stir bar, variac, RBF, condenser, tubing, hose clamps

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31
Q

for refill which tube does water enter from

A

the bottom tube

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32
Q

recrystallization steps

A
  1. Dissolve the solid in a minimal amount of hot solvent.
  2. Allow the solution to cool to room temperature.
  3. Cool further in an ice bath.
  4. Filter the mixture through a Buchner funnel to collect the solid.
  5. Weigh the solid to get a mass of compound recovered
  6. Measure the melting point
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33
Q

two solvent recrystallization

A

finding two pair of miscible solvents

  1. Choose solvent A that is very soluble to the compound. Choose solvent B that is does not dissolve the compound at all.
  2. Add hot solvent A to test tube containing compound. Heat, shake, dissolve the compound.
  3. Add hot solvent B. Reheat
  4. Cool solution
  5. Remove solvent via Buchner funnel to obtain crystals
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34
Q

TLC

A

thin layer chromatography

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35
Q

how to adjust eluent system if Rf is too low ** spots too close to baseline????

A

increase the polarity of eluent

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36
Q

what stains do we use for TLC

A

potassium permanganate, PMA

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37
Q

Aqueous or organic layer on top layer for separator funnel

A

Density is checked, typically organic is on the top

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38
Q

What is sodium sulphate used as

A

a drying agent

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39
Q

Seperation methods

A

Reduced pressure evaporation, vacuum filtration, gravity filtration

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40
Q

how do impurities effect melting point

A

if more than 10 degree difference then the product is impure

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41
Q

Info from NMR spectrum to identify

A

number of signals, chemical shift, integration, multiplicity

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42
Q

NMR downfield

A

left, desheilded

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43
Q

TMS peak on NMR

A

0

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44
Q

Solvent NMR peak

A

7.2 ppm

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45
Q

Integration NMR

A

area under the curve, proportional to the number of protons contained under the peak

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46
Q

NMR coupling

A

double peak on one signal, when nearby protons have a magnetic field that affect effective magnetic field. Number of peaks depends on the number of protons that are nearby and unique combinations of their spins
Spin-spin splitting is another name
n + 1 rule predicts number of peaks. N is the number of neighbors. Neighbors don’t include chemically equivalent H’s)

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47
Q

spin coupling

A

elimination of spin- spin splitting by constantly irradiating one type of nuclei at its resonance frequency

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48
Q

coupling constant

A

distance between the peaks of a multiplet

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49
Q

diasteromers

A

stereoisomers that are not mirror images

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50
Q

stereoisomers

A

molecules with the same chemical formula but different spatial arrangement

51
Q

enantiomers

A

isomers that are mirror images of each other

52
Q

what does chemical shift provide

A

info about the structural environment surrounding the protons producing the signal

53
Q

NMR symmetry

A

a symmetrical compound will have one signal for multiple protons not on the same carbon

54
Q

spin decoupling occurs

A

in the proton NMR of alcohols, amines, and carboxylic acids, resulting in the OH and NH protons appearing as broad singlets

55
Q

vicinal

A

substituents attached to adjacent carbons

56
Q

long range

A

attached to non adjacent carbons

57
Q

Diels-Alder reaction

A

a [4+2] cycloaddition reaction, 2 pi bonds broken, 2 sigma bonds formed, concerted

58
Q

dienophile

A

an alkene that reacts with a diene in a a diets-alder reaction

59
Q

diene

A

two double bonds

60
Q

dials alder mechanism

A

draw reaction scheme

61
Q

what is in the waterless condenser

A

ethylene glycol

62
Q

purpose of methanol in lab 3

A

extract crystals

63
Q

green chemistry

A

uses materials and processes that are intended to prevent or reduce pollution at its source

64
Q

lab 3

A

green chemistry and diets alder cycloaddition

65
Q

lab 4

A

dreidel crafts acylation

66
Q

dreidel crafts acylation mechanism

A

draw mechanism

67
Q

friedel crafts alkylation mechanism

A

for CH3Cl and 1 degree RCl, the Lewis acid-base complex itself serves as the electrophile for electrophilic aromatic substitution
* with 2 and 3 degree RCl, the Lewis acid-base complex reacts further to give a 2 or 3 degree carbocation, which serves as the electrophile; carbocation formation occurs only with 2 and 3 degree alkyl chlorides because they afford more stable carbocations

68
Q

friedel crafts acylation reagents

A

acyl chloride and AlCl3

69
Q

FeCl3 vs AlCl3

A

AlCl3 is difficult to store and more hygroscopic than FeCl3

70
Q

drawback of alkylation

A

further alkylation can occur, alkyl groups can rearrange into more stable carbo cations

71
Q

limiting agent in lab 4, acylation

A

4 methods benzoyl chloride

72
Q

anisole

A

draw image

73
Q

purpose of gas trap in lab 4

A

to catch Hal gas

74
Q

purpose of water in lab 4

A

quenching

75
Q

purpose of ethyl acetate in lab 4

A

solvent

76
Q

lab 5

A

Grignard reation

77
Q

Grignard reagent

A

an alkyl magnesium halide that is used to make carbon-carbon bonds

78
Q

Lab 5 purpose of THF

A

reaction solvent

79
Q

Issue with Grignard reagents

A

they decompose in protic solvents, alcohols, and amines to form alkanes

80
Q

Solvents that Grignard reagents won’t react with

A

diethyl ether or THF

81
Q

THF

A

draw image

82
Q

Grignard reaction mechanism

A

draw mechanism

83
Q

organometallic compounds

A

compounds that contain carbon- metal bonds

84
Q

wurtz coupling

A

coupling of two alkyl or cycloalkyl halides, produces dimers

85
Q

lab 5 limiting reagent

A

benzophenone

86
Q

side reactions of Grignard reaction

A

reactions with aldehydes
reactions with acyl chlorides and esters
reactions with ketones and carbon dioxide
reactions with alkyl bromide (wurtz coupling)

87
Q

Grignard reactions with aldehydes

A

form secondary alcohols

88
Q

Grignard reactions with acyl chlorides and esters

A

form corresponding alcohol

89
Q

Grignard reactions with ketone and carbon dioxide

A

form tertiary alcohols and carboxylic acids

90
Q

volume calculation

A

weight/ density

91
Q

molarity

A

the number of moles of solute per litre of solution

92
Q

% yield calculation

A

actual yield theoretical yield x 100

93
Q

% recovery calculation

A

amount recovered/ initial amount x 100

94
Q

% purity calculation

A

amount of pure/ amount of crude x 100

95
Q

lab 6

A

borohydride reduction

96
Q

reduction

A

gain of electrons, removal of O or addition of H

97
Q

reduction of carboxylic acids

A

primary alcohols

98
Q

reduction of aldehydes

A

primary alcohols

99
Q

reduction of esters

A

primary alcohols

100
Q

reduction of amides

A

primary amines

101
Q

reduction of ketones

A

secondary alcohols

102
Q

reducing agents

A

LiAlH4 NaBH4

103
Q

What can LiAlH4 reduce

A

aldehydes, ketones, esters, carboxylic acids

104
Q

what can NaBH4 reduce

A

aldehydes and ketones

105
Q

reduction mechanism

A

draw mechanism

106
Q

lab 6 limiting reagent

A

vanillin alcohol

107
Q

limiting reagent

A

the reactant use up first in a reaction

108
Q

NaOH purpose lab 6

A

solvent

109
Q

why is NaOH a solvent for reductions

A

reducing agents are unstable in acids

110
Q

Lab 6 HCl purpose

A

quenching

111
Q

borohydride reduction mechanism

A

draw mechanism

112
Q

lab 7

A

esterfication

113
Q

esterfication

A

the reaction of an alcohol with a carboxylic acid to produce an ester and water

114
Q

esterification mechanism

A

draw mechanism

115
Q

TMEDA

A

N,N,N,N tetramethylethylene diamine (draw)

116
Q

aldehyde

A

draw

117
Q

lab 7 product polarity

A

product is less polar (higher up on TLC plate)

118
Q

lab 8

A

aldol condensation

119
Q

aldol

A

contains both aldehyde and alcohol functional groups

120
Q

aldol condensation

A

A reaction in which an aldehyde or ketone acts as both the electrophile and nucleophile, resulting in the formation of a carbon-carbon bond in a new molecule called an aldol.

121
Q

lab 8 aldol condensation catalyst

A

acid or base

122
Q

aldol condensation mechanism

A

draw mechanism

123
Q
A

Organic Chem 2 (4 decks)

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