CH14 LEC: CMPNDS W/ O, S, OR HALOGENS

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OSU BIOPHRM 3311

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201 Terms

1
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disulfide originates from what rxn?

oxidation of 2 thiols

2
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Alpha Carbon (Cα) definition

the C atom directly attached to a functional group of interest

3
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alpha Cα always had ___ bonds

4 single

4
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alcohol functional group definition

an organic compound w/ an —OH group usually linked to a saturated C atom (AKA alpha C)

5
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<p>ID this structure</p>

ID this structure

typical structure of an alcohol, where R, R’, R” can be H, alkyl group, or similar groups, alone or in combination

6
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<p>ID this structure</p>

ID this structure

  • methanol

  • simplest alcohol

7
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<p>ID the family of this structure</p>

ID the family of this structure

alcohol

8
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<p>ID the family of this structure</p>

ID the family of this structure

alcohol (NOT phenol)

9
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<p>ID this structure</p>

ID this structure

  • phenol — not classified as an alcohol!

  • no primary, secondary, or tertiary alcohols

10
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aliphatic alcohols definition

organic compounds in which the —OH group is attached to an aliphatic C [straight-chain, branched, or non-aromatic ring structures]

11
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alcohols are classified as ___, ___, and ___ according to the number of Cs substituents (alkyl or R-groups) bonded to the alpha C (—C—OH)

primary, secondary, tertiary

12
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methanol’s (CH3OH) classification is considered ___ despite no alkyl group bond to the alkyl carbon

primary

13
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phenol compound definition

alcoholic aromatic compound w/ an —OH group replacing 1 H atom in a benzene ring

14
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benzene ring affects phenol’s ___ and ___, distinguishing it from aliphatic alcohols.

reactivity and properties

15
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recognize this: C6H6

benzene

16
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recognize this: C6H5OH or C6H6O

phenol

17
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recognize this: —C—O—C— …or… —R—O—R—

ether

18
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ether compound definition

any class of organic compounds that contains O b/t 2 alkyl or aryl groups (functional groups derived from aromatic ring)

19
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aryl group definition

functional group derived from an aromatic ring

20
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prefix in common naming of aliphatic alcohols: n—

indicates a straight chain

21
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prefix in common naming of aliphatic alcohols: iso—

branch at second-to-last C (Y shape)

22
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prefix in common naming of aliphatic alcohols: sec—

OH on a secondary C

23
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prefix in common naming of aliphatic alcohols: tert—

OH on a tertiary C

24
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prefix in common naming of aliphatic alcohols: neo—

C skeleton ends in quaternary C

25
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naming common names of aliphatic alcohols: what do we add as the suffix?

“alcohol” — i.e., “alkyl alcohol”

26
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naming common names of aliphatic alcohols: what number do we apply to the position of the —OH group?

the smallest number

27
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naming alcohols — IUPAC names: alcohols are named by replacing the suffix “—ane” of alkanes w/ ___.

“—anol”

28
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naming alcohols w/ alkyl substituent(s): the paren H—C chain includes the ___.

—OHs

29
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naming alcohols w/ alkyl substituent(s): number the C atoms of the parent chain beginning at ___.

the end nearer the alcohol functional group — then the other substituent groups.

30
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naming alcohols w/ alkyl substituent(s): add the location of the alcohol group by placing the number that locates the —OH group ___. 

immediately before the parent-suffix.

31
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naming alcohols w/ alkyl substituent(s): name and number the positions of the alkyl substituents___.

after you have numbered the —OH group

  • REMEMBER TO ALPHABETIZE 🙂

32
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naming alcohols w/ alkyl substituent(s): for alcohols w/ 2 OH groups, name as ___.

alkanediol — keep the “e”.

33
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naming alcohols w/ alkyl substituent(s): for alcohols w/ 3 OH groups, name as ___.

alkanetriol, and so on.

34
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naming alcohols w/ alkyl substituent(s): the chain is numbered so as to give one of the —OH groups the ___.

lowest possible number

35
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polyhydric alcohols definition

alcohols w/ 2 or 3 alcohol groups (—OH)

36
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cyclic alcohols definition

alcohols w/ cyclic hydrocarbons chains

37
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for cyclic alkanes and alkenes that contain an —OH group, name them as ___ and ___, respectively.

cycloalkanol and cycloalkenol

38
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for cyclic alkanes/enes naming: the —OH is presumed to be bound to the ___ and proceeds in the direction that gives the other substituent(s) or functional groups the ___.

  • 1st carbon — do not write!

  • lowest possible number

39
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to name compounds w/ a phenol or one other substituent: parent is ___ and assign the C attached to ___ as C1. 

  • phenol

  • —OH

40
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to name compounds w/ a phenol or one other substituent: number the Cs in the ring so that the substituent ___.

get the smallest number.

41
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to name compounds w/ a phenol or one other substituent: sometimes ___, ___, and ___ are used instead of numbers

o, m, and p

42
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naming alcohols as substituent: named as a substituent when other functional group w/ a ___ is present.

higher ranking (such as aldehyde)

43
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naming alcohols as substituent: as a substituent, the prefix for alcohol is ___.

“hydroxy”

44
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lower rankings of alcohols are ___, ___, and ___.

alkyl groups, alkanes/ynes, and halogens

45
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common names for methanol

methyl alcohol or wood alcohol

46
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uses of methanol

antifreeze, solvent, fuel, and to denature ethanol

47
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what does denaturing ethanol do

makes it undrinkable

48
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how is methanol toxic

it is not directly harmful, rather when it is metabolized in the body, it converts into toxic compounds (methanal and methanoic)

  • 15 mL leads to blindness

  • 30 mL leads to death

49
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recognize this: CH3OH

methanol

50
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recognize this: CH3CH2OH …or… C2H5OH …or… C2H6O

ethanol

51
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commons names for ethanol

ethyl alcohol or grain alcohol

52
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why is ethanol called grain alcohol

b/c it can be fermented from grains by a process called alcohol fermentation in yeast - it is present in all alcoholic beverages

53
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industrial ethanol production via ___

  • hydration of ethene in an addition rxn

  • ethene + water → ethanol

54
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ethanol is treated with denaturants ___ or ___ to make it unfit for human consumption

methanol or isopropanol

55
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industrial purpose of ethanol vs. beverage purpose of ethanol

ethanol used in beverages is subject to taxes, but when used in industrial purposes (cleaning products, fuels, solvents), these taxes can be avoided by adding denaturants to make it undrinkable

56
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recognize this: C3H2O

2-propanol

57
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common names for 2-propanol

isopropanol, isopryl alcohol, or rubbing alcohol

58
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uses of 2-propanol

common solvent, used to sterilize instruments, and as a skin cleanser before drawing blood or giving injections

59
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hand sanitizer contains 70—80% of ___.

ethanol

60
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<p>ID this structure: common and IUPAC name</p>

ID this structure: common and IUPAC name

  • ethylene glycol

  • 1,2-ethanediol

61
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ethylene glycol does NOT contain ___.

C=C

62
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characteristics of ethylene glycol

  • 2 —OH groups

  • colorless liquid

  • miscible w/ H2O

  • sweet taste

  • lethal to humans and dogs

63
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common use of ethylene glycol

antifreeze

64
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<p>ID this structure: common and IUPAC name</p>

ID this structure: common and IUPAC name

  • glycerol or glycerin

  • 1,2,3-propanetriol

65
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characteristics of glycerol 

  • contains 3 Cs, each bound to an —OH group

  • nontoxic liquid

  • miscible w/ H2O

  • forms structural backbone of fats and oils

66
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common use of glycerol

used as moisturizer b/c —OH groups interact w/ H2O

67
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<p>ID this structure</p>

ID this structure

triacylglycerol

68
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<p>ID this structure</p>

ID this structure

serine

69
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<p>ID this structure</p>

ID this structure

glucose

70
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<p>ID this structure</p>

ID this structure

threonine

71
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<p>ID this structure</p>

ID this structure

cholesterol

72
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<p>ID this structure</p>

ID this structure

ribose

73
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<p>ID this structure</p>

ID this structure

deoxyribose

74
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2 kinds of alcohols

aliphatic and phenols

75
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2 kinds of ethers

saturated (alkyl) and unsaturated (aryl)

76
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<p>ID this structure</p>

ID this structure

ether

77
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aryl group definition

  • indicates aromatic functional group

  • Ar—OH

78
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ethers can be present in (attached to or integrated in) these four forms

linear, cyclic, ring, or benzene rings

79
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ether common naming: the prefix “di—” is used if ___.

both the alkyl groups are the same

80
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ether common naming: ID the ___ groups attached in the O atom

2 alkyl 

81
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ether common naming: put the alkyl groups in ___ w/ spaces b/t the names and followed by the word ___.

  • alphabetical order

  • ether

82
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ether IUPAC naming: ID ___ groups connected to O atom

alkane/alkyl

83
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ether IUPAC naming: select the ___ alkyl group as the parent chain, and name it as an ___.

  • alkyl group

  • alkane

84
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ether IUPAC naming: name the shorter alkyl group and add the suffix ___ to indicate it is part of the ether

“—oxy”

85
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ether IUPAC naming: number the C atoms in the parent chain to provide the lowest numbers for the ___.

O atom

86
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ether IUPAC naming: ethers are typically names as ___ w/in a larger molecule(s)

substituents

87
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ether IUPAC naming: the smaller, shorter alkyl group becomes the ___, and the larger alkyl group becomes the ___.

  • alkoxy substituent

  • alkane root name

88
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ether IUPAC naming: in ROR’, R’ is larger than R and is named as ___.

alkoxyalkane

89
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ether IUPAC naming: an —OR group is referred to as an ___.

alkoxy group

90
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3 major types of intermolecular forces

  1. London dispersion forces

  2. Dipole-dipole

  3. Hydrogen bonding

91
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all molecules experience this force

london dispersion forces

92
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london dispersion forces definition

at any given moment, there might be an unequal distribution of e- w/in a molecule, leading to a momentary polarity and then a temporary attractive force

93
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LDFs strength

weak force

94
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LDFs intensity influenced by what

size and structure of molecules

95
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LDFs are the only intermolecular interactions for ___ molecules

nonpolar - i.e., hydrocarbons

96
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larger the molecular weight and surface area, the ___ the forces, and ___ BP

  • greater

  • higher

97
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BP ___ as alkanes increase in size

increase

98
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branching ___ intermolecular interactions mainly b/c it ___ the surface area available for contact b/t molecules

  • decreases

  • decreases

99
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BP ___ w/ ___ branching in isomers

  • decreases

  • increased

100
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dipole-dipole forces definition

electrostatic attraction force b/t positive and negative ends of polar molecules