final exam helpful reagents Flashcards
(125 cards)
1
Q
NaH
with an alcohol
A
A very strong base, used to deprotonate an alcohol to give an alkoxide ion.
2
Q
Na
with an alochol
A
Will react with an alcohol to liberate hydrogen gas, giving an alkoxide ion.
3
Q
NaBH4, MeOH
with a ketone or aldehyde
A
A reducing agent (source of nucleophilic hydride). Can be used to reduce ketones or aldehydes to alcohols. Will not reduce esters or carboxylic acids.
4
Q
1) LiAlH4
2) H3O+
with ketones, aldehydes, esters, or carboxylic acids
A
A strong reducing agent (source of nucleophilic hydride). Can be used to reduce ketones, aldehydes, esters, or carboxylic acids to give an alcohol.
5
Q
H2, Pt
when used with alkenes and/or alkynes or (oca) ketones and/or aldehydes
A
Reducing agent. Generally used to reduce alkenes and/or alkynes to alkanes, but in some cases, it can also be used to reduce ketones and/or aldehydes to alcohols.
6
Q
Mg
with an organohalide
A
Can be used to convert an organohalide (RX, where R = alkyl, aryl or vinyl group) into a Grignard reagent (RMgX).
7
Q
RMgX
with aldehydes or ketones
A
A Grignard reagent. Examples include MeMgBr, EtMgBr and PhMgBr. These reagents are very strong nucleophiles (and very strong bases as well), and they will react with aldehydes or ketones. Aldehydes are converted into secondary alcohols (except for formaldehyde which is converted to a primary alcohol), while ketones are converted to tertiary alcohols. Esters are converted to tertiary alcohols when treated with excess Grignard.
8
Q
TMSCl, Et3N
with an alcohol
A
Trimethylsilyl chloride [(CH3)3SiCl], in the presence of a base (such as triethylamine), will protect an alcohol (ROH is converted to ROTMS).
9
Q
TBAF
with ROTMS
A
Tetrabutylammonium fluoride. Used for deprotection of alcohols with silyl protecting groups (ROTMS is converted to ROH).
10
Q
HX
with an alcohol
A
HBr and HCl are strong acids that also provide a source of a strong nucleophile. Can be used to convert an alcohol into an alkyl bromide or alkyl chloride.
11
Q
TsCl, pyridine
with an alcohol
A
Tosyl chloride (TsCl) will convert an alcohol into a tosylate. This is important because it converts a bad leaving group (HO−) into a good leaving group (TsO−).
12
Q
PBr3
with a primary or secondary alcohol
A
Phosphorus tribromide (PBr3) can be used to convert a primary or secondary alcohol into an alkyl bromide. If the OH group is connected to a chiral center, we expect inversion of configuration (typical for an SN2 process).
13
Q
SOCl2, pyridine
with a primary or secondary alcohol
A
Thionyl chloride (SOCl2) can be used to convert a primary or secondary alcohol into an alkyl chloride. If the OH group is connected to a chiral center, reaction conditions can be selected for inversion of configuration (typical for an SN2 process).
14
Q
HCl, ZnCl2
with an alchohol
A
Can be used to convert an alcohol into an alkyl chloride.
15
Q
Na2Cr2O7, H2SO4, H2O
with primary or secondary alcohol (why not tertiary)
A
A mixture of sodium dichromate (Na2Cr2O7) and sulfuric acid (H2SO4) gives chromic acid, which is a strong oxidizing agent. Primary alcohols are oxidized to give carboxylic acids, while secondary alcohols are oxidized to give ketones. Tertiary alcohols are generally unreactive.
16
Q
PCC, CH2Cl2
with a primary or secondary alcohol
A
Pyridinium chlorochromate (PCC) is a mild oxidizing agent that will oxidize a primary alcohol to give an aldehyde, rather than a carboxylic acid. Secondary alcohols are oxidized to give ketones. Methylene chloride (CH2Cl2) is a solvent.
17
Q
DMP, CH2Cl2
with a primary or secondary alcohol
A
DMP (Des-Martin Periodinane) is a mild oxidizing agent that will oxidize a primary alcohol to give an aldehyde, rather than a carboxylic acid. Secondary alcohols are oxidized to give ketones.
18
Q
1) DMSO, (COCl)2,
2) Et3N
with a primary or secondary alcohol
A
Dimethyl sulfoxide (DMSO), oxalyl chloride [(COCl)2], and triethyl amine (Et3N) are the reagents for a Swern oxidation, which will oxidize a primary alcohol to give an aldehyde, rather than a carboxylic acid. Secondary alcohols are oxidized to give ketones.
19
Q
RX
with an alcohol or thiol
A
An alkyl halide. Used for the alkylation of alcohols or thiols. First, the alcohol or thiol is deprotonated with a base, such as NaH or NaOH, and the resulting anion is then treated with the alkyl halide, thereby installing an alkyl group.
20
Q
1) Hg(OAc)2, ROH
2) NaBH4
with an alkene
A
These reagents will achieve alkoxymercuration-demercuration of an alkene. This process adds H and OR in a Markovnikov fashion across the alkene.
21
Q
HX
with a dialkyl or an epoxide
A
Will convert a dialkyl ether into two alkyl halides via cleavage of the C–O bonds. Will also react with an epoxide, thereby opening the ring, and installing a halogen at the more-substituted position.
22
Q
MCPBA
with an alkene
A
meta-Chloroperoxybenzoic acid. An oxidizing agent that will convert an alkene into an epoxide.
23
Q
RCO3H
with an alkene
A
A peroxy acid. An oxidizing agent that will convert an alkene into an epoxide. MCPBA is an example of a peroxy acid
24
Q
1) Br2, H2O
2) NaOH
with an alkene
A
Alternative reagents for converting an alkene into an epoxide
25
(CH3)3COOH, Ti[OCH(CH3)2]4, (+)-DET or (–)-DET
| with
Reagents for enantioselective (Sharpless) epoxidation.
26
NaOR (or RONa)
| with an alkyl halide or epoxide in williamson ether synthesis
An alkoxide ion is both a strong nucleophile and a strong base. It can be used in a Williamson ether synthesis (reacts with an alkyl halide to form an ether), or to open an epoxide under basic conditions (the alkoxide ion attacks the less-substituted position).
27
NaCN
| with an epoxide
A good nucleophile that will react with an epoxide in a ring-opening reaction
28
NaSH
| with an epoxide
A very strong nucleophile that will react with an epoxide in a ring-opening reaction. NaSH can also be used to prepare thiols from alkyl halides.
29
RMgBr
| with an epoxide
A Grignard reagent. A strong base and a strong nucleophile. Will react with an epoxide in a ring-opening reaction, to attack the less-substituted side (it is not possible to use acidic conditions and have the Grignard reagent attack the more-substituted side – see the previous section on common mistakes to avoid).
30
LiAlH4
| with an epoxide
Lithium aluminum hydride is a source of nucleophilic hydride. It will react with an epoxide in a ring-opening reaction, to attack the less-substituted side (it is not possible to use acidic conditions and have a hydride ion attack the more-substituted side – see the previous section on common mistakes to avoid).
31
[H+], H2O (or H3O+)
| with an epoxide
Aqueous acidic conditions. Under these conditions, an epoxide is opened to give a trans diol
32
[H+], ROH
| with an epoxide
Under these conditions, an epoxide is opened, with a molecule of the alcohol attacking a protonated epoxide at the more-substituted position.
33
NaOH/H2O, Br2
| with a thiol
Reagents for converting thiols into disulfides
34
HCl, Zn
| with a disulfide
Reagents for converting disulfides into thiols
35
H2O2
| with a sulfide or sulfoxide
Strong oxidizing agent, used to oxidize sulfides to sulfoxides, and then further to sulfones.
36
NaIO4
Oxidizing agent, used to oxidize sulfides to sulfoxides
37
t-BuOK
| with 1,2 dibromide or an allylic bromide
A strong, sterically hindered base, used to convert a 1,2-dibromide or an allylic bromide into a conjugated diene
38
HBr
| with a conjugated pi system
Will add across a conjugated π system to give two products: a 1,2-adduct and a 1,4-adduct
39
Br2
| with a conjugated pi system
Will add across a conjugated π system to give two products: a 1,2-adduct and a 1,4-adduct
40
1,3-Butadiene. Can serve as a diene in a Diels-Alder reaction
41
1,3-Cyclopentadiene. Can serve as a diene in a Diels-Alder reaction
42
Can serve as a dienophile in a Diels-Alder reaction, especially if the substituents (X) are electron-withdrawing groups. The cis configuration of the dienophile is preserved in the product
43
Can serve as a dienophile in a Diels-Alder reaction, especially if the substituents (X) are electron-withdrawing groups. The trans configuration of the dienophile is preserved in the product
44
Can serve as a dienophile in a Diels-Alder reaction, especially if the substituents (X) are electron-withdrawing groups
45
heat
| ONLY reagant
When you see “heat” without any other reagents indicated, consider the possibility of a pericyclic reaction (cycloaddition, electrocyclic reaction, or a sigmatropic rearrangement)
46
hv
When you see this term (pronounced H-new), or “light”, without any other reagents indicated, consider the possibility of an electrocyclic reaction
47
Na2Cr2O7, H2SO4, H2O
| benzylic rxn
Sodium dichromate and sulfuric acid give chromic acid, which is a strong oxidizing agent that can be used to oxidize a benzylic position, provided that the benzylic position is not quaternary. The alkyl group (connected to the aromatic ring) is converted into a carboxylic acid group.
48
1. KMnO4, H2O, heat
2. H3O+
| benzylic rxn
Potassium permanganate. A strong oxidizing agent that can be used to oxidize a benzylic position, provided that the benzylic position is not quaternary. The alkyl group (connected to the aromatic ring) is converted into a carboxylic acid group.
49
NBS, heat
| benzylic rxn
N-Bromosuccinimide. A reagent that is used for radical bromination at the benzylic position
50
H2O
| benzylic rxn
Water is a weak nucleophile that can be used in an SN1 reaction with a benzylic halide
51
NaOH
| benzylic rxn
Hydroxide is a strong nucleophile that can be used in an SN2 reaction with a primary benzylic halide.
52
conc. H2SO4
| with an oh
A strong acid that can be used to achieve acid-catalyzed dehydration to give an alkene
53
NaOEt
| with secondary or tertiary halides
Sodium ethoxide is a strong base that can be used to convert secondary or tertiary halides into alkenes (via an E2 process)
54
3 H2, 100 atm, 150ºC
| benzene
Conditions for complete hydrogenation of benzene to give cyclohexane
55
Na, CH3OH, NH3
| with benzene ring
Reagents for a Birch reduction, which reduces a benzene ring to give a 1,4-cyclohexadiene ring.
56
Br2, AlBr3 or FeBr3
bromination
| with an aromatic ring
Installation of a bromine atom on an aromatic ring
57
Br2
bromination
| with a moderately or strongly activated aromatic ring
Installation of a bromine atom on a moderately or strongly activated aromatic ring
58
Cl2, AlCl3 or FeCl3
chlorination
| with an armoatic ring
Installation of a chlorine atom on an aromatic ring
59
Cl2
chlorination
| with a moderately or strongly activated aromatic
Installation of a chlorine atom on a moderately or strongly activated aromatic ring
60
HNO3, H2SO4
nitration
| with an aromatic ring
Installation of a nitro group on an aromatic ring. Cannot be performed if an amino group is already present on the aromatic ring
61
Fuming H2SO4
sulfonation
| with a benzene ring
Installation of a sulfonic acid group, often used as a blocking group
62
Dilute H2SO4
desulfonation
Removes a sulfonic acid group
63
RCl, AlCl3
Friedel-Crafts alkylation
| with benzne
Installation of an alkyl group on an aromatic ring. This process is limited to R groups that are not susceptible to carbocation rearrangements. Unless otherwise indicated, assume conditions will favor monoalkylation. This reaction cannot be performed on a moderately or strongly deactivated aromatic ring
64
friedel-crafts acylation
Installation of an acyl group on an aromatic ring. This reaction cannot be performed on a moderately or strongly deactivated aromatic ring
65
1. Fe or Zn, HCl
2. NaOH
Reduction
Reduction of a nitro group to give an amino group
66
Excess NBS
Benzylic bromination
Exhaustive bromination of the benzylic position
67
1. KMnO4, H2O, heat
2. H3O+
Benzylic oxidation
Oxidation of the benzylic position to give a carboxylic acid
68
Zn(Hg), HCl, heat
Clemmensen reduction
| with ketone or aldheyde carbonyl group
Reduction of a ketone or aldehyde carbonyl group to give a methylene (CH2) group (from a ketone) or a methyl (CH3) group (from an aldehyde)
69
NaOH
SNAr or elimination-addition
| with aromatic
A strong nucleophile used in nucleophilic aromatic substitution reactions as well as elimination-addition reactions
70
NaNH2
elimination-addition
A very strong base (and strong nucleophile) used in elimination-addition reactions
71
H3O+
Hydrolysis of acetals imines, or enamines
Treating an acetal, an imine, or an enamine with H3O+ generates a carbonyl group via hydrolysis
72
[H+], 2 ROH,
(− H2O)
| with an aldehyde or ketone
Acetal formation
Conversion of an aldehyde or ketone into an acetal. The acetal group can be used to protect aldehydes and ketones. The acetal group is stable to basic conditions but is removed when subjected to aqueous acidic conditions to regenerate the carbonyl group (a process called hydrolysis)
73
[H+], HOCH2CH2OH,
− H2O
| with an aldehyde or ketone
Cyclic acetal formation
Ethylene glycol can be used to convert an aldehyde or ketone into an acetal. The acetal group can be used to protect aldehydes and ketones. The acetal group is stable to basic conditions but is removed when subjected to aqueous acidic conditions to regenerate the carbonyl group (a process called hydrolysis)
74
[H+], HSCH2CH2SH,,
(− H2O)
| with an aldehyde or ketone
Cyclic thioacetal formation
Ethylene thioglycol can be used to convert an aldehyde or ketone into a cyclic thioacetal
75
Raney nickel
| with thioacetal
Desulfurization
Converts a thioacetal (or cyclic thioacetal) to an alkane.
76
[H+], RNH2,
(− H2O)
| with an aldehyde or ketone
Imine formation
A primary amine (or ammonia) converts an aldehyde or ketone into an imine. The imine group is removed when subjected to aqueous acidic conditions to regenerate the carbonyl group (a process called hydrolysis)
77
[H+], R2NH,
(− H2O)
| with an aldehyde or ketone
Enamine formation
A secondary amine converts an aldehyde or ketone into an enamine. The enamine group is removed when subjected to aqueous acidic conditions to regenerate the carbonyl group (a process called hydrolysis)
78
[H+], NH2OH,
(− H2O)
| with an aldehyde or ketone
Oxime formation
Converts an aldehyde or ketone into an oxime.
79
[H+], NH2NH2,
(− H2O)
| with an aldehyde or ketone
Hydrazone formation
Converts an aldehyde or ketone into a hydrazone
80
NaOH, H2O, heat
| with a hydrazone
Wolff-Kishner reduction
Reduces a hydrazone to an alkane
81
1. LiAlH4
2. H3O+
| with an aldehyde or ketone
Reduces an aldehyde or ketone to an alcohol
82
1. RMgBr
2. H3O+
| with an aldehyde or ketone
Grignard reaction
When an aldehyde or ketone is treated with a Grignard reagent (followed by aqueous acidic workup), a carbon-carbon bond-forming reaction occurs, giving an alcohol that exhibits the newly formed C–C bond
83
HCN, KCN
| with an aldehyde or ketone
Converts an aldehyde or ketone into a cyanohydrin
84
When an aldehyde or ketone is treated with a Wittig reagent, a carbon-carbon bond-forming reaction occurs, giving an alkene that exhibits the newly formed C=C double bond in the location of the former carbonyl group. If R is a simple alkyl group, such as methyl or ethyl, then the (Z) alkene is generally observed to be the major product
85
Wittig reaction
A stabilized Wittig reagent that will react with an aldehyde or ketone to give the (E) alkene as the major product
86
HWE reaction (Horner-Wadsworth- Emmons)
A HWE reagent functions like a stabilized Wittig reagent. It will react with an aldehyde or ketone to give the (E) alkene as the major product
87
RCO3H
| with an aldehyde or ketone
Baeyer-Villiger oxidation
Converts a ketone into an ester (via insertion of an oxygen atom). Converts an aldehyde into a carboxylic acid (via insertion of an oxygen atom)
88
[H3O+], Br2
| with a ketone (or aldehyde)
α-Bromination
These reagents can be used to install a bromine atom at the T position of a ketone (or aldehyde). Subsequent treatment of the resulting α-bromoketone with pyridine gives an α,β-unsaturated ketone. This two-step process can be used to introduce α,β-unsaturation into a ketone or aldehyde.
89
1. Br2, PBr3
2. H2O
| with a carboxylic acid
Hell-Volhard-Zelinsky reaction
These reagents can be used to install a bromine atom at the α position of a carboxylic acid.
90
1.NaOH, Br2
2.H3O+
| with a methyl ketone
Haloform reaction
These reagents can be used to convert a methyl ketone into a carboxylic acid. This process is most efficient when the other α position (of the starting ketone) bears no protons.
91
NaOH, H2O
| with two equivalents of an aldehyde or ketone
Aldol addition reaction
Aqueous sodium hydroxide will cause an aldol addition reaction between two equivalents of an aldehyde or ketone to give a β-hydroxyaldehyde (or a β-hydroxyketone).
92
NaOH, H2O, heat
| with two equivalents of an aldehyde or ketone
Aldol condensation
Aqueous sodium hydroxide and heat will cause an aldol condensation between two equivalents of an aldehyde or ketone to give an α,β-unsaturated aldehyde (or an α,β-unsaturated ketone).
93
1. NaOEt
2. H3O+
| with two equivalents of an ester
Claisen condensation
These reagents will cause two equivalents of an ester to undergo a condensation reaction, giving a β-ketoester. An acidic aqueous workup is required to afford the neutral product.
94
1. LDA, -78ºC
2. RX
| with a ketone
Alkylation
These conditions can be used to install an alkyl group at the less-substituted α position of an unsymmetrical ketone (via the kinetic enolate).
95
1. NaH, 25ºC
2. RX
| with a ketone
Alkylation
These conditions can be used to install an alkyl group at the more-substituted α position of an unsymmetrical ketone (via the thermodynamic enolate).
96
| with NaOEt, alkyl halide, and H3O heat
Acetoacetic ester synthesis
Ethyl acetoacetate can be converted into a derivative of acetone upon treatment with ethoxide, followed by an alkyl halide, followed by hydrolysis and decarboxylation with aqueous acid and heat.
97
treatment with ethoxide, followed by an alkyl halide, followed by hydrolysis and decarboxylation with aqueous acid and heat.
Malonic ester synthesis
Diethyl malonate can be converted into a substituted carboxylic acid (more specifically, a derivative of acetic acid) upon treatment with ethoxide, followed by an alkyl halide, followed by hydrolysis and decarboxylation with aqueous acid and heat.
98
1. R2CuLi
2. H3O+
| with a suitable Michael acceptor
Michael reaction
A lithium dialkylcuprate is a weak nucleophile and can serve as a Michael donor. It will undergo conjugate addition with a suitable Michael acceptor (see Table 21.2).
99
NaCN
| with an alkyl halide
This reagent will react with an alkyl halide to give a nitrile. Subsequent hydrolysis of the nitrile gives a carboxylic acid, with one more carbon atom than the starting alkyl halide.
100
1) Mg
2) CO2
3) H3O
| with an alkyl halide
These reagents can be used to convert an alkyl halide into a carboxylic acid, with the introduction of one carbon atom. Insertion of magnesium gives a Grignard reagent, which then attacks carbon dioxide to give a carboxylate ion, which is then protonated upon acidic workup
101
1) LiAlH4
2) H3O+
| with ketones, aldehydes, esters, or carboxylic acids
Lithium aluminum hydride is a powerful hydride reducing agent. It will reduce ketones, aldehydes, esters, and carboxylic acids to give alcohols. Reduction of esters and carboxylic acids requires the use of excess LiAlH4. Reduction of an amide (with LiAlH4) gives an amine
102
pyridine
Pyridine is a weak base that is often used to neutralize for reactions that produce a strong acid as a by-product.
103
SOCl2
| with carboxylic acid or amide
Thionyl chloride can be used to convert a carboxylic acid into an acid halide. This reagent can also be used to dehydrate an amide to give a nitrile
104
ROH
| with an acid chloride or an acid anhydride
Alcohols are weak nucleophiles and weak bases. An alcohol can be used to convert an acid chloride or an acid anhydride into an ester
105
NH3
| with an acid chloride or an acid anhydride
Ammonia is both a base and a nucleophile. Excess ammonia can be used to convert an acid chloride or an acid anhydride into an amide
106
RNH2
| with an acid chloride or an acid anhydride
Secondary amines are bases and nucleophiles. Excess amine can be used to convert an acid chloride or an acid anhydride into an amide
107
1) xs RMgBr
2) H3O+
| with an acid chloride, an acid anhydride, an ester, or a nitrile
A Grignard reagent is a strong nucleophile. Two equivalents of a Grignard reagent will react with an acid chloride, with an anhydride, or with an ester, followed by aqueous acidic workup, to give an alcohol (with the introduction of two R groups). A Grignard reagent will also react with a nitrile, followed by hydrolysis, to give a ketone.
108
R2CuLi
| with an acid chloride
A lithium dialkylcuprate is a weak nucleophile. It will react with an acid chloride to give a ketone, but it will not react with ketones or esters
109
1) LiAl(OR)3H
2) H3O+
| with an acid chloride or an acid anhydride
Lithium trialkoxyaluminum hydrides are reducing agents that will convert an acid chloride or an acid anhydride into an aldehyde, without subsequent reduction of the resulting aldehyde.
110
1) DIBAH
2) H3O+
| with an ester
Diisobutylaluminum hydride is a hydride reducing agent that will convert an ester into an aldehyde.
111
H3O+
| with an acid chloride, anhydride, esterm amide, or nitrile
Aqueous acid will cause hydrolysis of an acid chloride, an anhydride, an ester, an amide, or a nitrile to give a carboxylic acid.
112
[H+], ROH
| with carboxylic acid
Under acidic conditions, an alcohol will react with a carboxylic acid via a Fischer esterification, giving an ester
113
1. NaCN
2. xs LiAlH4
3. H2O
| with an alkyl halide
Preparation of an amine (from an alkyl halide)
These reagents can be used to convert an alkyl halide into an amine with the introduction of one carbon atom (from the cyano group).
114
1. SOCl2
2. xs NH3
3. xs LiAlH4
4. H2O
| with a carboxylic acid
Preparation of an amine (from a carboxylic acid)
These reagents can be used to convert a carboxylic acid into an amine, without a change in the carbon skeleton
115
1. Fe, H3O+
2. NaOH
| with an aryl nitro group
Reduction
These reagents can be used to reduce an aryl nitro group into an amino group. The first step employs acidic conditions, so the amine is protonated (under the conditions of its formation) to give an ammonium ion. The ammonium ion is then deprotonated upon basic workup, giving the amine.
116
1. NaN3
2. LiAlH4
3. H2O
| with an alkyl halide
Azide synthesis
These reagents can be used to convert an alkyl halide into an amine, without a change in the carbon skeleton. The last two steps (reduction and water workup) can be replaced with hydrogenation in the presence of a metal catalyst (H2, Pt).
117
Gabriel synthesis
Phthalimide is the starting material for the Gabriel synthesis, which can be used to prepare primary amines. Phthalimide is treated with KOH to give potassium phthalimide, which is then treated with an alkyl halide, giving an SN2 reaction. The product of the SN2 process is then hydrolyzed (upon treatment with hydrazine or aqueous acid) to release the amine.
118
NaBH3CN
| reaction occurs between a ketone (or aldehyde) and an amine (or ammonia)
Reductive amination
In the presence of an acid catalyst, sodium cyanoborohydride can be used to achieve a reductive amination. The reaction occurs between a ketone (or aldehyde) and an amine (or ammonia). This process can be used to convert a primary amine into a secondary amine. Similarly, a secondary amine is converted into a tertiary amine.
119
Acetylation
An amine will undergo acetylation (giving an amide) when treated with acetyl chloride.
120
1. Excess CH3I
2. Ag2O, H2O, heat
Hofmann elimination
These reagents can be used to achieve elimination of H and NH2 to give an alkene. When there are two possible regiochemical outcomes for the elimination process, the less substituted alkene predominates.
121
NaNO2, HCl
| with a primary amine
Reactions with nitrous acid
A mixture of sodium nitrite and HCl will convert a primary amine into a diazonium salt. Under the same conditions, a secondary amine is converted into an N-nitrosamine
122
CuBr or CuCl or CuI or CuCN
| with an an aryldiazonium salt
Sandmeyer reaction
When an aryldiazonium salt is treated with CuBr, the diazonium group is replaced with a bromine atom
When an aryldiazonium salt is treated with CuCl, the diazonium group is replaced with a chlorine atom
When an aryldiazonium salt is treated with CuI, the diazonium group is replaced with a iodine atom
When an aryldiazonium salt is treated with CuCN, the diazonium group is replaced with a cyano group
123
HBF4
| with an an aryldiazonium salt
Fluorination (Schiemann reaction)
When an aryldiazonium salt is treated with HBF4, the diazonium group is replaced with a fluorine atom
124
H2O, heat
| with an an aryldiazonium salt
Preparation of phenol
When an aryldiazonium salt is treated with water and heat, the diazonium group is replaced with an OH group
125
H3PO2
| with an an aryldiazonium salt
Reduction
When an aryldiazonium salt is treated with H3PO2, the diazonium group is replaced with a hydrogen atom
