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Organic Chemistry Flashcards

1
Q

_______________
- detection and study of electromagnetic radiation absorbed by an organic molecule

A

Absorption spectroscopy

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2
Q

In absorption spectroscopy, the most important regions are ___________, __________, & __________.

A

Infrared (IR)
Ultraviolet /visible (UV/Vis)
Radio frequency (RF)

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3
Q

_______________ spectroscopy
- uses radiation from middle of infrared spectrum
- Energies of photons in this region correspond to energy differences between vibrational states (modes) in covalent bonded molecules

A

IR

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4
Q

The 2 type of vibrational modes in spectroscopy
____________
____________

A

Bends (bond angles change)
Stretches (bond lengths change)

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5
Q

2 types is stretches are __________ & __________

A

Symmetric
Asymmetric

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6
Q

4 types of bends are __________, __________, __________, & __________

A

Rocking
Scissoring
Wagging
Twisting

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7
Q

An IR spectrum is plotted as percent transmittance vs frequency & instead of using reciprocal time (s^-1), the frequency is given in reciprocal wavelengths called _________________

A

Wave numbers

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8
Q

IR spectrum
4,000-1,300 cm^-1 is called the ____________________ region
1,500-500 cm^-1 is called the _______________ region

A

Functional group region
Fingerprint region

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9
Q

____________ energy absorption
- leads to a change in a molecules electron configuration
- In organic compounds with double bonds the absorption results in promotion of electrons from Bonding molecular orbitals to higher energy Anti-bonding molecular orbitals

A

UV/Vis energy absorption

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10
Q

The energy change in which electrons from Bonding molecular orbitals are promoted to higher energy Anti-bonding molecular orbitals is called ____________

A

π —> π* transition

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11
Q

Other kinds of electron transitions can occur when radiation is absorbed, if certain functional groups are present
- If a C=O Bond is present then an n —> π* transition is observed where n is a _______________ molecular orbital

A

Non-bonding molecular orbital

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12
Q

Energy absorbed during electron transitions is measured & interpreted in order to provide ____________ information about the molecule being irradiated (also degree of unsaturation & conjugation)

A

Structural information

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13
Q

__________ spectra of organic compounds
- Recorded by a radiating samples with continually increasing wavelengths of radiation (higher to lower energy)
- The energy of radiation is sufficient to promote an electron to a higher energy level then the energy is absorbed & absorption is observed as a positive peak
- Spectra displayed with wavelength in nanometers at the bottom of the graph & relative absorption (unitless) along left vertical axis

A

UV/Vis

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14
Q

________ spectroscopy
- Detection & presentation of absorbed RF radiation
- Signals are due to absorption of RF radiation by nuclei
- Only nuclei with nuclear spin are suitable for this spectroscopy (such as H & C-13)
- All nuclei are positively charged
- Those that spin create their own magnetic field which can interact with external magnetic fields

A

NMR spectroscopy

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15
Q

Proton (H) NMR signals
- usually spins of protons are randomly oriented and when exposed to a strong external magnetic field they become aligned with it called _________ or against it called _________

A

Parallel
Anti-parallel

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16
Q

When a lower energy proton in the parallel state, absorbs the right amount of energy supplied by the radio-frequency radiation then it can be promoted into the higher energy anti-parallel state and the proton is _____-_______ & is in resonance with the applied radio-frequency radiation

A

Spin-flipped

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17
Q

Energy absorbed during a spin-flip is represented as a ________ in the spectrum

A

Peak

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18
Q

______________ spectra
- plotted with relative intensity of RF absorption peaks on the vertical axis & position of peaks on the horizontal axis
- Peak positions are plotted from high frequency to low frequency (from left to right)
- Absorption peak positions are measured relative to a reference signal produced by tetramethylsilane (TMS)

A

H NMR

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19
Q

_____________ defines position of NMR signals which are measured in ppm

A

Chemical shift

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20
Q

Ratio of ____/_____ leads to a parts per million (ppm) unit system

A
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21
Q

The ________ signal is assigned 0 ppm

A

TMS

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22
Q

The number of absorption peaks seen in spectrum indicates number of magnetically (equivalent OR non-equivalent) protons in a molecule

A

Non-equivalent

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23
Q

In position of the peaks (chemical shifts), the magnetic environments of protons are __________ or __________

A

Shielded
Unshielded

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24
Q

__________ protons feel the external magnetic field less & signals found upfield (closer to the TMS peak)
__________ protons feel the external magnetic field more & signals appear downfield (farther from the TMS peak)

A

Shielded
De-shielded

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25
Q

____________ is caused by non-equivalent neighboring Hydrogens’ magnetic fields interacting & if a hydrogen has no immediate neighbors then its absorption signal is a single peak (singlet)

A

Splitting

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26
Q

________________ rule
- The number is peaks from an absorption signal equals the number of its neighboring Hydrogens + 1

A

n + 1 rule

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27
Q

_______________
- selective partitioning of substance into a phase that is easily removed

A

Extraction

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28
Q

____________ extraction
- Use of 2 immiscible liquids to selectively partition a compound into 1 of the liquids
- Neither liquid can react in irreversible way with desired compound
- Extracting liquid added to the compound solution must have a higher affinity for the solute than the solvent in which the solute is dissolved (the higher partition coefficient is better)
- A partitioned solute needs to be easy to remove

A

Liquid-liquid extraction

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29
Q

____________ funnel
- Laboratory glassware used for liquid-liquid extraction

A

Separatory funnel

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30
Q

The extraction of weak acids & weak bases are often accomplished by using _______________ extraction (both of these classes of compound can be converted to water soluble salts)

A

Liquid-liquid extraction

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31
Q

_______________
- preferential vaporization of a liquid with a high vapor pressure & then condensing the vapor back to a liquid to collect it
- used to separate 2 or more miscible liquids
- The larger the difference between the liquid boiling points then the easier the separation

A

Distillation

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32
Q

__________ distillation
- used to separate low-temperature boiling liquids that have large differences in between their boiling points

A

Simple distillation

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33
Q

_______________ distillation
- used for separation of liquids that boil above 150°C
- Pressure is lowered by a vacuum source so that liquids vapor pressures increase (can boil at lower temperatures)
- Can prevent heat induced decomposition
- Requires a boiling point difference of at least 30°C for good separation

A

Vacuum distillation

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34
Q

_______________
- can separate liquids whose boiling points are closer to each other than 30°C
- Uses a fractionating column placed between the still head & pot

A

Frictional distillation

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35
Q

_______________
- separation techniques involving use of a stationary phase & mobile phase

A

Chromatography

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36
Q

_______________
- stationary phase is a thin layer of medium coated onto glass, plastic, or metal plate
- common media are silica gel, alumina (highly polar)

A

Thin layer chromatography

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37
Q

_______________
- sensitive procedure that uses a gas chromatogram & the stationary phase is a viscous silicone oil that coats the inside of a long thin glass column housed inside the instrument
- mobile phase —> gas He or N2

A

Gas liquid chromatography

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38
Q

_______________
- automated packed column chromatography that uses prepacked media columns with high separation ability for nonvolatile compounds (those with high boiling points)
- Mobile phase is a solvent system

A

High-performance liquid chromatography

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39
Q

_______________ methods
- used to separate mixtures of enantiomers
- When a mixture of enantiomers is passed through a column packed with a traditional stationary phase then the enantiomers travel at the same rate & there is no separation
- if chiral packing is used then stereoisomers move at different rates & are separated

A

Chromatographic methods

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40
Q

_______________ methods
- large molecules such as enzymes may have a preference for only one optical isomer & will use only that is in reactions at catalyzes
- the other isomer is unreacted & unchanged which results in different compounds with different properties that can be separated by traditional methods
- Used for separation of enantiomers

A

Enzymatic methods

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41
Q

_______________
- a hydrocarbon compound that is referred to as a saturated hydrocarbons because they contain the max number of Hydrogen atoms possible for their molecular structures

A

Alkane

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42
Q

Naming of Alkanes can be divided into 2 categories of compounds : __________ structures & __________ structures

A

Normal structures & cyclic structures

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43
Q

Melting & boiling points of normal alkanes show a regular (increase or decrease) as the number of carbons in their chains increases

A

Increases

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44
Q

All alkanes are (hydrophobic or hydrophilic) with relatively low densities & are flammable

A

Hydrophobic

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45
Q

True or false
Alkane combustion reactions are of commercial importance

A

True

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46
Q

_______________
- a hydrocarbon compound that is referred to as unsaturated because it contains a C=C double bond (so structure does not have max number of Hydrogens)

A

Alkene

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47
Q

True or False
The chain from which the alkene’s name is derived must be the longest in the molecule that contains the double bond

A

True

48
Q

Alkene’s may have more than 1 double bonds & if so then a prefix must be added: diene means _____ double bonds
triene means _____ double bonds

A

2
3

49
Q

True or false
If stereochemistry around a double bond is shown then it must be specified in the name (cis/trans or E/Z)

A

True

50
Q

Alkenes are similar to Alkanes except they are slightly more (polar or nonpolar) due to the π portion of double bonds

A

Polar

51
Q

Trans- alkenes are usually less polar than cis- alkenes due to __________

A

symmetry

52
Q

Alkenes can be prepared by __________ reactions such as dehydration of alcohols & dehydrohalogenation of alkyl halides

A

elimination

53
Q

2 common mechanisms for alkene forming elimination reactions are ____________ elimination & ___________ elimination

A

Monomolecular elimination (E1)
Bimolecular elimination (E2)

54
Q

____________ elimination
- 1st order kinetics
- 2 steps:
1. rate determining step where formation of intermediate carbocation from loss of H2O molecule or halogen ion
2. fast step where loss of a proton adjacent to carbocation produces an alkene

A

Monomolecular elimination (E1)

55
Q

_______________ elimination (E2)
- 2nd order kinetics
- 1 step
1. A proton is abstracted from a carbon next to a carbon with a leaving group then as the proton is abstracted the remaining electron pair moves between adjacent carbons thus the leaving group depart with a pair of electrons producing an alkene

A

Bimolecular (E2)

56
Q

_______________
- oxygen atoms are added to double bond carbon atoms (sp2 hybridized)
- double bond may be completely cleaved

A

Alkene oxidation

57
Q

_______________
- a hydrocarbon compound that contains a carbon-carbon triple bond functional group & also referred to as unsaturated

A

Alkyne

58
Q

Principal chain from which alkyne’s name is derived must be the longest in the molecule that contains the triple bond & multiple triple bonds are indicated by using _______________

A

Greek prefixes

59
Q

Because carbons in the triple bonds are sp hybridized then these groups (do or do not) exhibit stereochemical isomerism

A

Do not

60
Q

Alkynes are similar to Alkanes and Alkenes except they are slightly more (polar or nonpolar) due to their triple bonds

A

Polar
- triple bonds are even more polarizable

61
Q

Synthesis of alkyne functional groups is limited to a few _____________ reactions

A

Elimination

62
Q

_______________ compounds
- contains the arene functional group
- 6-membered carbon ring with 3 alternating C=C double bonds
- many IUPAC accepted common names for monosubstituted aromatic compounds

A

Aromatic compounds

63
Q

2 types of arene-type functional groups :
__________ aromatic compounds
__________ aromatic compounds

A

Heterocyclic aromatic compounds
Polycyclic aromatic compounds

64
Q

__________ aromatic compounds
- 1 or more carbon atoms are replaced with heteroatoms (e.g., N)

A

Heterocyclic

65
Q

__________ aromatic compounds
- 2 or more arene rings fused together

A

Polycyclic aromatic compounds

66
Q

_______________
- contains hydroxyl group bonded to sp3-hybridized carbon atom

A

Alcohol

67
Q

Alcohol nomenclature :
replace the -e suffix of an alkane with the suffix ________

A

-ol
(methane becomes methanol)

68
Q

The longest carbon chain is considered the __________ chain

A

Principal chain

69
Q

For complex alcohols you identify the longest carbon chain containing the carbon with the hydroxyl group & then its position is given the lowest possible number & the root name is derived from the __________ chain

A

Principal chain

70
Q

The conversion of alkenes to alcohols uses _______________ reactions

A

alkene addition reactions

71
Q

_______________
- a type of reaction that involves a lone pair
of electrons on a nucleophile attacking an electron deficient electrophilic center & the nucleophile bonds to the electrophilic center, resulting in the expulsion of a leaving group
- can be used for alcohol synthesis

A

Bimolecular nucleophilic substitution

72
Q

_______________
- a type of reaction that involves replacing a functional group or atom with another negatively charged atom or group & the reaction proceeds through a two-stage mechanism, with heterolysis preceding the reaction with the nucleophile

A

Unimolecular nucleophilic substitution

73
Q

Unimolecular nucleophilic substitution also produces an alcohol but often low yield & if a branched alkyl halide is reacted with a hydroxide base in a polar solvent then the products are primarily __________

A

Alkenes

74
Q

Alcohol reactions are varied but the most important are __________ reactions

A

Oxidation reactions

75
Q

Alcohol substitution reaction rates are improved by transforming __________ to mesylate or tosylate

A

hydroxyl

76
Q

Aromatic alcohols are called ________ and have a hydroxyl group attached to arene ring

A

Phenols

77
Q

The nomenclature of phenols are named in the same way as substituted benzene compounds but the root name is always __________

A

phenol

78
Q

__________ is readily oxidized to benzoquinone & is important because benzoquinone is easily reduced to hydroquinone (critical for cellular respiration)

A

Phenol

79
Q

Aldehydes & Ketones contain the _________ functional group which has a C=O double bond

A

Carbonyl

80
Q

Aldehyde nomenclature replaces the -e suffix of alkane with the suffix _______

A

-al
(methane becomes methanal)

81
Q

When the aldehyde group is a substituent then the prefix ________ is used

A

formyl-

82
Q

Ketone nomenclature replaces the -e suffix of the alkane with ________

A

-one
(propane becomes propanone)

83
Q

When the Ketone group is a substituent then the prefix ______ is used

A

oxo-

84
Q

The polarized ________ group causes aldehydes & ketones to have an elevated boiling point due to dipole-dipole intermolecular attractive forces

A

carbonyl

85
Q

True or False
The partially negatively charged Oxygen in the carbonyl acts as a hydrogen acceptor with molecules such as water & alcohols and the partially positively charged carbon in the carbonyl acts as an electrophile & makes hydrogens on carbons directly adjacent to it

A

True

86
Q

Oxidation of primary alcohols –> gives __________

A

aldehydes

87
Q

Oxidation of secondary alcohols –> gives __________

A

ketones

88
Q

Oxidation cleavage of alkenes with a vinylic hydrogen –> gives __________

A

aldehydes

89
Q

Oxidation cleavage of alkenes with no vinylic hydrogens –> gives __________

A

ketones

90
Q

Hydroboration/oxidation of terminal alkynes –> gives __________

A

aldehydes

91
Q

Hydroboration/oxidation of internal alkynes –> gives __________

A

ketones

92
Q

Partial reduction of esters–> gives __________

A

aldehydes

93
Q

____________ reaction for aldehydes & ketones
- attack of partially positive carbon (electrophile) in carbonyl group by neutral & negatively charged nucleophiles

A

Nucleophilic addition reaction

94
Q

____________
- functional group contains hydroxyl group bonded to carbonyl carbon

A

Carboxylic acid

95
Q

Carboxylic acid nomenclature replaces the -e suffix of alkane with __________

A

-oic acid

96
Q

True of False
Carboxyl group is terminal & designated number 1 in principal chain of molecule

A

True

97
Q

Oxidation of alcohols –> gives ________

A

Carboxylic acids

98
Q

Oxidation of aldehydes –> gives ________

A

Carboxylic acids

99
Q

Oxidative cleavage of alkenes –> gives __________

A

Carboxylic acids

100
Q

Oxidative cleavage of alkynes –> gives __________

A

Carboxylic acids

101
Q

Reduction reaction of a carboxylic acid produces a _______________

A

primary alcohol

102
Q

The _______________ is a substitution reaction in which replaces a C-H bond on the alpha-carbon of a carboxylic acid with a C-Br bond (alpha-bromination)

A

Hell-Volhard-Zelinsky

103
Q

Decarboxylation of a carboxylic acid is a process that removes carbon dioxide from carboxylic acids to produce ____________ (which has 1 less carbon atom than the original carboxylic acid)

A

Alkanes
(ethanoic acid to ethane)

104
Q

Esterification reaction of a carboxylic acid produces an _________ & _______

A

Ester & Water

105
Q

Esterification is a type of condensation reaction that occurs when a carboxylic acid reacts with an alcohol & is also known as the _______________ (during the reaction the oxygen atom becomes connected to a carbon on both sides forming an ester so carboxylic acid loses an OH & the alcohol loses a H which combine to form water)

A

Fischer esterification

106
Q

The carboxylic acid derivative _____________ is a functional group that contains a chlorine atom bonded to a carbonyl carbon

A

Acid chloride

107
Q

Carboxylic acid derivative Acid Chloride nomenclature changes the suffix ‘-ic acid’ to ___________

A

-yl chloride

108
Q

Carboxylic acid derivative ____________ is a functional group that contains an Oxygen atom bonded to 2 carbonyl carbon atoms

A

Anhydrides

109
Q

2 forms of Anhydrides are __________ & __________

A

Symmetrical & Mixed

110
Q

Carboxylic acid derivative Anhydride nomenclature for symmetrical are named by replacing the suffix ‘acid’ with __________ & Mixed are named by __________ the names of both acids and replacing the suffix ‘acid’ with __________

A

anhydride
alphabetizing & anhydride

111
Q

Carboxylic acid derivative __________ is a functional group that has an O bonded to carbonyl C atom & is sp3-hybridized C

A

Ester

112
Q

Carboxylic acid derivative Ester nomenclature named as though ester derived from dehydration product of an alcohol reacting with carboxylic acid & part contributed from alcohol comes first in name and is usually an alkyl group & part contributed from carboxylic acid appears second in name and is an acyl group
- you change the suffix ‘-ic acid’ to a suffix _________

A

-ate

113
Q

Carboxylic acid derivative __________ is a functional group that contains a nitrogen atom bonded to a carbonyl carbon atom (hydrogen atoms or other groups may be bonded to nitrogen)

A

Amide

114
Q

Carboxylic acid derivative Amide nomenclature has the primary amides (no R groups) replace the suffix ‘-ic acid’ of carboxylic acid contributing the acyl group with the suffix _______

A

amide

115
Q

With secondary & tertiary amides , the alkyl groups attached to the nitrogen atom must be named and If different groups are attached, then they are alphabetized & given a prefix ________

A

N-

116
Q

The ____________ rearrangement transforms primary amides into primary amines

A

Hofmann

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