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organic chemistry 1 > unit 3 - ch 10 & 11 > Flashcards

unit 3 - ch 10 & 11 Flashcards

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1
Q

define an alcohol

A

a compound in which a hydrogen atom of a hydrocarbon has been replaced by a hydroxyl group (-OH)

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2
Q

define a diol

A

an organic compound that contains 2 alcohol (-OH) groups

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3
Q

define a phenol

A

an organic compound with a hydroxyl group bonded directly to an aromatic ring

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4
Q

the boiling point of alcohols are _____ (high/lower) than similar molecular mass compounds.
why?

A

higher because of H-bonding

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5
Q

the solubility of _____ (shorter/longer) alcohols are very similar to water because of the hydroxyl group

A

shorter carbon chains (ethanol)

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6
Q

what is the 5 C solubility rule?

A

for every 5 Cs you want to dissolve in water you need one OH group

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7
Q

the acidity of an alcohol _____ (increases/decreases) as the number of carbons increase

A

decreases - increased pKa

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8
Q

why do halogens and other electron withdrawing groups increase acidity?

A

inductive effects produced by the alkoxide ion

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9
Q

what is THF?

A

a typical solvent used for its stabilizing effects

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10
Q

sodium hydride is a _____ (stronger/weaker) base than sodium or potassium

A

stronger base

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11
Q

form an alkoxide ion using the following reactants

A
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12
Q

why is phenol more acidic than cyclohexanol?
draw the conjugate bases of both molecules

A

phenol’s conjugate base is very stable because of resonance, making the acid phenol very strong

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13
Q

bonding carbon to metallic elements is good for what?

A

forming new C-C bonds

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14
Q

define Grignard’s reagent

A

an organomagnesium halide, written in the form R-Mg-X

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15
Q

what kind of solvent is used to stabilize Grignard reagents?
give an example

A

dry ethers
ex. CH3CH2OCH2CH3

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16
Q

give the following halide’s reactivity when bonded to an R group from highest to lowest
R-Br, R-F, R-I, R-Cl

A

R-I > R-Br > R-Cl&raquo_space; R-F

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17
Q

give a 2 step mechanism for the addition of organometallic reagents to carbonyl compounds beginning with the following reactant

A
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18
Q

show which 3 reactants/solvents to use to get from this reactant to this product & in what order

A
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19
Q

show which 3 reactants/solvents to use to get from this reactant to this product & in what order

A
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20
Q

show the steps of synthesis to get from this reactant to this product

A
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21
Q

show the steps of synthesis to get from this reactant to this product

A
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22
Q

which type of reagent reacts well with electrophilic multiple bonds like the following?

A

organometallic reagents

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23
Q

which 3 reagents can be used to reduce a carbonyl group like seen below?

A

NaBH4
LiAlH4
H2 + Raney Nickel

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24
Q

show the structure of NaBH4 and LiAlH4 as they act as reagents

A
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25
Q

show the mechanism & reagents for reducing a carbonyl group beginning with the reactant below

A
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26
Q

NaBH4 is _____ (strong/weak), and will react with which of the following?
aldehydes/carboxylic acids/esters/ketones

A

weak
reacts with aldehydes and ketones
not with esters or carboxylic acids

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27
Q

LiAlH4 is _____ (strong/weak), and will react with which of the following?
aldehydes/carboxylic acids/esters/ketones

A

strong
reacts with all 4

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28
Q

give the products that result from reacting the following reactants

A
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29
Q

give the products that result from reacting the following reactants

A
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30
Q

what is raney nickel?
what types of bonds can it reduce?

A

a hydrogen rich nickel powder that is more reactive than Pd or Pt catalysts
can reduce double and triple bonds within a molecule

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31
Q

give the products that result from reacting the following reactants & solvents

A
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32
Q

beginning with the following reactant, show the products when it is reacted with Raney Nickel + H2 vs when it is reacted with NaBH4

A
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33
Q

define a thiol

A

the sulfur analogue of an alcohol, R-S-H

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34
Q

thiols are ______ (more/less) acidic than oxygen
why?

A

more acidic due to the weaker S-H bond

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35
Q

_____ (Sn1/Sn2/E1/E2) reactions can be used to make thiols
give a basic reaction mechanism beginning with the following reactants

A

Sn2

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36
Q

give the product(s) that result from combining the following reactants

A
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37
Q

oxidation may/does involve which 3 features, concerning O(2), H2, and X2

A

addition of O or O2
loss of H2
addition of X2 (halogens)

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38
Q

reduction may/does involve which 3 features, concerning O(2), H2, and X2

A

addition of H2 or H-
loss of O or O2
loss of X2 (halogens)

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39
Q

PCC ______ (oxidizes/reduces) alcohols, except for which kind? why?

A

PCC oxidizes alcohols except for tertiary because there are no available H atoms on the carbinol atom

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40
Q

oxidation only takes place when which types of bonds are broken?

A

carbon-carbon

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41
Q

chromic acid oxidizes secondary alcohols to which functional group?
give a reaction example using this reactant

A

to ketones

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42
Q

what is the formula for chromic acid?
which solvent is used along with it?

A

Na2Cr2O7
+ H2SO4

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43
Q

chromic acid oxidizes primary alcohols to which functional group?
give a reaction example using this reactant

A

carboxylic acids

44
Q

pyridinium chlorochromate (PCC) oxidizes primary alcohols to which functional group?
give a reaction example using this reactant

A

aldehydes

45
Q

what is collins reagent?

A

Cr2O3 in pyridine

46
Q

what is jones reagent?

A

chromic acid in acetone

47
Q

which 4 solvents are involved in swern oxidation? at what condition(s)?

A

DMSO
(COCl)2
Et3N
CH2Cl2
at -60 degrees C

48
Q

how does swern oxidation affect alcohols?

A

oxidizes alcohols to ketones and aldehydes

49
Q

how does dess-martin periodinane affect alcohols?

A

oxidizes primary alcohols to aldehydes and secondary alcohols to ketones

50
Q

what are five 6 methods of alcohol oxidation besides using chromic acid and PCC?

A

collins reagent
jones reagent
bleach
KMnO4 and nitric acid
swern oxidation
dess-martin periodinane

51
Q

sodium hypochlorite (NaOCl) oxidizes primary alcohols to ________ (functional group) and secondary alcohols to _____ (functional group)

A

primary to carboxylic acids
secondary to ketones

52
Q

give the product(s) resulting from the following reactants?

A
53
Q

give the product(s) resulting from the following reactants?

A
54
Q

secondary alcohols are oxidized to ketones using which 2 chromium reagents and which 3 chromium-free reagents?

A

chromium: chromic acid, PCC
chromium-free: NaOCl, Swern, DMP

55
Q

primary alcohols are oxidized to aldehydes using which 1 chromium reagent and which 2 chromium-free reagents?

A

chromium: PCC
chromium-free: swern, DMP

56
Q

primary alcohols are oxidized to carboxylic acids using which 1 chromium reagent and which 1 chromium-free reagent?

A

chromium: chromic acid
chromium-free: NaOCl

57
Q

define alcohol dehydrogenase (ADH)

A

an enzyme used by living cells to catalyze the oxidation of ethanol to acetaldehyde

58
Q

give the product(s) formed when combining the following reactant with ADH

A
59
Q

define aldehyde dehydrogenase (ALDH)

A

an enzyme used by living cells to catalyze the oxidation of acetaldehyde to acetic acid

60
Q

give the product(s) formed when combining the following reactant with ALDH

A
61
Q

which bond of the following molecule is broken when alcohols react as nucleophiles?

A

the O-H bond

62
Q

which bond of the following molecule is broken when alcohols react as electrophiles?

A

the C-O bond

63
Q

define tosylate ester

A

an ester of an alcohol with p=toluenesulfonic acid

64
Q

give the products for this reaction given the following reactants

A
65
Q

tosylate reactions can undergo ________ (elimination/substitution/both) reactions

A

both elimination and substitution

66
Q

which reagent is best for reducing alcohols?

A

tosylates

67
Q

when using hydrobromic acid, primary alcohols go by the ______ (Sn1/Sn2) mechanism

A

Sn2

68
Q

when using hydrobromic acid, secondary and tertiary alcohols go by the _____ (Sn1/Sn2) mechanism

A

Sn1

69
Q

give the 3 step mechanism for the reaction of a tertiary alcohol with HBr beginning with the following reactant

A
70
Q

give the 2 step mechanism for the reaction of a primary alcohol with HBr beginning with the following reactant

A
71
Q

what comprises the lucas reagent?
why is the combo necessary?

A

HCl and ZnCl2
combo is necessary because chloride is a weaker nuc than bromide and ZnCl2 is used to promote the reaction

72
Q

give the 2 step mechanism for the reaction of a secondary alcohol with lucas reagent beginning with the following reactant

A
73
Q

give the 1 step mechanism for the reaction of a primary alcohol with lucas reagent beginning with the following reactant

A
74
Q

define the lucas test

A

a test used to determine whether an alcohol is primary, secondary, or tertiary

75
Q

what are the time frames of primary, secondary, and tertiary results of the lucas test?

A

primary: >6 min
secondary: 1-5 min
tertiary: <1 min

76
Q

what are 2 benefits of reacting alcohols with phosphorus halides (PBr3/PCl3)?

A

good yield with primary and secondary alcohols
rearrangement is uncommon

77
Q

what phosphorus halides are used for adding bromide, chloride, and iodide?

A

PBr3
PCl3
P + I2 (PI3 not stable)

78
Q

give the 2 step mechanism for reacting an alcohol with PBr3 beginning with R-O-H

A
79
Q

give the structure of thionyl chloride

A
80
Q

what is the general result when reacting alcohols with thionyl chloride?

A

alcohols convert into corresponding alkyl chloride

81
Q

give the 5 step mechanism and products when reacting alcohols with thionyl chloride beginning with R-OH

A
82
Q

what are the best chloride reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?

A

primary: SOCl2
secondary: SOCl2
tertiary: HCl

83
Q

what are the best bromide reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?

A

primary: PBr3 or HBr (in select cases)
secondary: PBr3
tertiary: HBr

84
Q

what are the best iodide reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?

A

primary: P/I2
secondary: P/I2
tertiary: HI

85
Q

which solvent at what condition is used for dehydration reactions of alcohols?

A

H2SO4 above 180 degrees C

86
Q

give the 3 step reaction mechanism for dehydration of alcohols beginning with the following reactant

A
87
Q

of the 3 steps to dehydrate an alcohol, which step is the rate limiting step?

A

formation of the carbocation - high energy & unstable

88
Q

what occurs in a bimolecular dehydration reaction to form ethers? why kind of reaction is it?

A

two alcohols react by Sn2 mechanism to form an ether

89
Q

which solvent at what condition is used for dehydration reactions of alcohols?

A

H2SO4 below 140 degrees C favors ethers

90
Q

give the 2 step mechanism for bimolecular dehydration to form ethers beginning with the following reactant

A
91
Q

define pinacol rearrangement

A

when a vicinal diol converts to a ketone under acidic conditions and heat

92
Q

give the 4 step mechanism for pinacol rearrangement beginning with the following reactant

A
93
Q

which solvent at what condition is used for pinacol rearrangements>

A

H2SO4 at 100 degrees C

94
Q

which 3 reagents are used to complete periodic acid cleavage of glycols?

A

OsO4, H2O2, HIO4

95
Q

complete a periodic acid cleavage of glycol reaction beginning with ethene

A
96
Q

complete a periodic acid cleavage of glycol reaction beginning with the following reactant

A
97
Q

define fischer esterification

A

the acid-catalyzed reaction of an alcohol with a carboxylic acid to form an ester

98
Q

what is the catalyst in a fischer esterification reaction?

A

sulfuric acid

99
Q

give the products of this reaction beginning with the following reactants

A
100
Q

ester formation using acid chlorides achieves ______ (higher/lower) yields than fischer esterification

A

higher yields

101
Q

give a general ester formation using acid chlorides reaction beginning with the following reactants

A
102
Q

williamson ether synthesis has best results with ______ (primary/secondary/tertiary) alkyl halides

A

primary

103
Q

which reaction mechanism is completed in williamson ether synthesis?

A

Sn2

104
Q

what are the possible reagents used for williamson ether synthesis?

A

Na, NaH, or K

105
Q

give the 2 step mechanism for williamson ether synthesis beginning with R-OH + Na

A

organic chemistry 1 (2 decks)

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