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

unit 3 - ch 10 & 11 Flashcards

(105 cards)

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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a compound in which a hydrogen atom of a hydrocarbon has been replaced by a hydroxyl group (-OH)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
show the mechanism & reagents for reducing a carbonyl group beginning with the reactant below
26
NaBH4 is _____ (strong/weak), and will react with which of the following? aldehydes/carboxylic acids/esters/ketones
weak reacts with aldehydes and ketones not with esters or carboxylic acids
27
LiAlH4 is _____ (strong/weak), and will react with which of the following? aldehydes/carboxylic acids/esters/ketones
strong reacts with all 4
28
give the products that result from reacting the following reactants
29
give the products that result from reacting the following reactants
30
what is raney nickel? what types of bonds can it reduce?
a hydrogen rich nickel powder that is more reactive than Pd or Pt catalysts can reduce double and triple bonds within a molecule
31
give the products that result from reacting the following reactants & solvents
32
beginning with the following reactant, show the products when it is reacted with Raney Nickel + H2 vs when it is reacted with NaBH4
33
define a thiol
the sulfur analogue of an alcohol, R-S-H
34
thiols are ______ (more/less) acidic than oxygen why?
more acidic due to the weaker S-H bond
35
_____ (Sn1/Sn2/E1/E2) reactions can be used to make thiols give a basic reaction mechanism beginning with the following reactants
Sn2
36
give the product(s) that result from combining the following reactants
37
oxidation may/does involve which 3 features, concerning O(2), H2, and X2
addition of O or O2 loss of H2 addition of X2 (halogens)
38
reduction may/does involve which 3 features, concerning O(2), H2, and X2
addition of H2 or H- loss of O or O2 loss of X2 (halogens)
39
PCC ______ (oxidizes/reduces) alcohols, except for which kind? why?
PCC oxidizes alcohols except for tertiary because there are no available H atoms on the carbinol atom
40
oxidation only takes place when which types of bonds are broken?
carbon-carbon
41
chromic acid oxidizes secondary alcohols to which functional group? give a reaction example using this reactant
to ketones
42
what is the formula for chromic acid? which solvent is used along with it?
Na2Cr2O7 + H2SO4
43
chromic acid oxidizes primary alcohols to which functional group? give a reaction example using this reactant
carboxylic acids
44
pyridinium chlorochromate (PCC) oxidizes primary alcohols to which functional group? give a reaction example using this reactant
aldehydes
45
what is collins reagent?
Cr2O3 in pyridine
46
what is jones reagent?
chromic acid in acetone
47
which 4 solvents are involved in swern oxidation? at what condition(s)?
DMSO (COCl)2 Et3N CH2Cl2 at -60 degrees C
48
how does swern oxidation affect alcohols?
oxidizes alcohols to ketones and aldehydes
49
how does dess-martin periodinane affect alcohols?
oxidizes primary alcohols to aldehydes and secondary alcohols to ketones
50
what are five 6 methods of alcohol oxidation besides using chromic acid and PCC?
collins reagent jones reagent bleach KMnO4 and nitric acid swern oxidation dess-martin periodinane
51
sodium hypochlorite (NaOCl) oxidizes primary alcohols to ________ (functional group) and secondary alcohols to _____ (functional group)
primary to carboxylic acids secondary to ketones
52
give the product(s) resulting from the following reactants?
53
give the product(s) resulting from the following reactants?
54
secondary alcohols are oxidized to ketones using which 2 chromium reagents and which 3 chromium-free reagents?
chromium: chromic acid, PCC chromium-free: NaOCl, Swern, DMP
55
primary alcohols are oxidized to aldehydes using which 1 chromium reagent and which 2 chromium-free reagents?
chromium: PCC chromium-free: swern, DMP
56
primary alcohols are oxidized to carboxylic acids using which 1 chromium reagent and which 1 chromium-free reagent?
chromium: chromic acid chromium-free: NaOCl
57
define alcohol dehydrogenase (ADH)
an enzyme used by living cells to catalyze the oxidation of ethanol to acetaldehyde
58
give the product(s) formed when combining the following reactant with ADH
59
define aldehyde dehydrogenase (ALDH)
an enzyme used by living cells to catalyze the oxidation of acetaldehyde to acetic acid
60
give the product(s) formed when combining the following reactant with ALDH
61
which bond of the following molecule is broken when alcohols react as nucleophiles?
the O-H bond
62
which bond of the following molecule is broken when alcohols react as electrophiles?
the C-O bond
63
define tosylate ester
an ester of an alcohol with p=toluenesulfonic acid
64
give the products for this reaction given the following reactants
65
tosylate reactions can undergo ________ (elimination/substitution/both) reactions
both elimination and substitution
66
which reagent is best for reducing alcohols?
tosylates
67
when using hydrobromic acid, primary alcohols go by the ______ (Sn1/Sn2) mechanism
Sn2
68
when using hydrobromic acid, secondary and tertiary alcohols go by the _____ (Sn1/Sn2) mechanism
Sn1
69
give the 3 step mechanism for the reaction of a tertiary alcohol with HBr beginning with the following reactant
70
give the 2 step mechanism for the reaction of a primary alcohol with HBr beginning with the following reactant
71
what comprises the lucas reagent? why is the combo necessary?
HCl and ZnCl2 combo is necessary because chloride is a weaker nuc than bromide and ZnCl2 is used to promote the reaction
72
give the 2 step mechanism for the reaction of a secondary alcohol with lucas reagent beginning with the following reactant
73
give the 1 step mechanism for the reaction of a primary alcohol with lucas reagent beginning with the following reactant
74
define the lucas test
a test used to determine whether an alcohol is primary, secondary, or tertiary
75
what are the time frames of primary, secondary, and tertiary results of the lucas test?
primary: >6 min secondary: 1-5 min tertiary: <1 min
76
what are 2 benefits of reacting alcohols with phosphorus halides (PBr3/PCl3)?
good yield with primary and secondary alcohols rearrangement is uncommon
77
what phosphorus halides are used for adding bromide, chloride, and iodide?
PBr3 PCl3 P + I2 (PI3 not stable)
78
give the 2 step mechanism for reacting an alcohol with PBr3 beginning with R-O-H
79
give the structure of thionyl chloride
80
what is the general result when reacting alcohols with thionyl chloride?
alcohols convert into corresponding alkyl chloride
81
give the 5 step mechanism and products when reacting alcohols with thionyl chloride beginning with R-OH
82
what are the best chloride reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?
primary: SOCl2 secondary: SOCl2 tertiary: HCl
83
what are the best bromide reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?
primary: PBr3 or HBr (in select cases) secondary: PBr3 tertiary: HBr
84
what are the best iodide reagents to use for converting primary, secondary, and tertiary alcohols to alkyl halides?
primary: P/I2 secondary: P/I2 tertiary: HI
85
which solvent at what condition is used for dehydration reactions of alcohols?
H2SO4 above 180 degrees C
86
give the 3 step reaction mechanism for dehydration of alcohols beginning with the following reactant
87
of the 3 steps to dehydrate an alcohol, which step is the rate limiting step?
formation of the carbocation - high energy & unstable
88
what occurs in a bimolecular dehydration reaction to form ethers? why kind of reaction is it?
two alcohols react by Sn2 mechanism to form an ether
89
which solvent at what condition is used for dehydration reactions of alcohols?
H2SO4 below 140 degrees C favors ethers
90
give the 2 step mechanism for bimolecular dehydration to form ethers beginning with the following reactant
91
define pinacol rearrangement
when a vicinal diol converts to a ketone under acidic conditions and heat
92
give the 4 step mechanism for pinacol rearrangement beginning with the following reactant
93
which solvent at what condition is used for pinacol rearrangements>
H2SO4 at 100 degrees C
94
which 3 reagents are used to complete periodic acid cleavage of glycols?
OsO4, H2O2, HIO4
95
complete a periodic acid cleavage of glycol reaction beginning with ethene
96
complete a periodic acid cleavage of glycol reaction beginning with the following reactant
97
define fischer esterification
the acid-catalyzed reaction of an alcohol with a carboxylic acid to form an ester
98
what is the catalyst in a fischer esterification reaction?
sulfuric acid
99
give the products of this reaction beginning with the following reactants
100
ester formation using acid chlorides achieves ______ (higher/lower) yields than fischer esterification
higher yields
101
give a general ester formation using acid chlorides reaction beginning with the following reactants
102
williamson ether synthesis has best results with ______ (primary/secondary/tertiary) alkyl halides
primary
103
which reaction mechanism is completed in williamson ether synthesis?
Sn2
104
what are the possible reagents used for williamson ether synthesis?
Na, NaH, or K
105
give the 2 step mechanism for williamson ether synthesis beginning with R-OH + Na

organic chemistry 1 (2 decks)

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