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Organic Chemistry (CHE 3332) > final exam helpful reagents > Flashcards

final exam helpful reagents Flashcards

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1
Q

NaH

with an alcohol

A

A very strong base, used to deprotonate an alcohol to give an alkoxide ion.

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2
Q

Na

with an alochol

A

Will react with an alcohol to liberate hydrogen gas, giving an alkoxide ion.

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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.

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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.

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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.

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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).

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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.

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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).

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9
Q

TBAF

with ROTMS

A

Tetrabutylammonium fluoride. Used for deprotection of alcohols with silyl protecting groups (ROTMS is converted to ROH).

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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.

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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−).

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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).

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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).

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14
Q

HCl, ZnCl2

with an alchohol

A

Can be used to convert an alcohol into an alkyl chloride.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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22
Q

MCPBA

with an alkene

A

meta-Chloroperoxybenzoic acid. An oxidizing agent that will convert an alkene into an epoxide.

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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

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24
Q

1) Br2, H2O
2) NaOH

with an alkene

A

Alternative reagents for converting an alkene into an epoxide

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25
Q

(CH3)3COOH, Ti[OCH(CH3)2]4, (+)-DET or (–)-DET

with

A

Reagents for enantioselective (Sharpless) epoxidation.

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26
Q

NaOR (or RONa)

with an alkyl halide or epoxide in williamson ether synthesis

A

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).

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27
Q

NaCN

with an epoxide

A

A good nucleophile that will react with an epoxide in a ring-opening reaction

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28
Q

NaSH

with an epoxide

A

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.

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29
Q

RMgBr

with an epoxide

A

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).

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30
Q

LiAlH4

with an epoxide

A

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).

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31
Q

[H+], H2O (or H3O+)

with an epoxide

A

Aqueous acidic conditions. Under these conditions, an epoxide is opened to give a trans diol

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32
Q

[H+], ROH

with an epoxide

A

Under these conditions, an epoxide is opened, with a molecule of the alcohol attacking a protonated epoxide at the more-substituted position.

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33
Q

NaOH/H2O, Br2

with a thiol

A

Reagents for converting thiols into disulfides

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34
Q

HCl, Zn

with a disulfide

A

Reagents for converting disulfides into thiols

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35
Q

H2O2

with a sulfide or sulfoxide

A

Strong oxidizing agent, used to oxidize sulfides to sulfoxides, and then further to sulfones.

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36
Q

NaIO4

A

Oxidizing agent, used to oxidize sulfides to sulfoxides

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37
Q

t-BuOK

with 1,2 dibromide or an allylic bromide

A

A strong, sterically hindered base, used to convert a 1,2-dibromide or an allylic bromide into a conjugated diene

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38
Q

HBr

with a conjugated pi system

A

Will add across a conjugated π system to give two products: a 1,2-adduct and a 1,4-adduct

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39
Q

Br2

with a conjugated pi system

A

Will add across a conjugated π system to give two products: a 1,2-adduct and a 1,4-adduct

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40
Q
diels-alder
A

1,3-Butadiene. Can serve as a diene in a Diels-Alder reaction

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41
Q
diels-alder
A

1,3-Cyclopentadiene. Can serve as a diene in a Diels-Alder reaction

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42
Q
diels-alder
A

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

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43
Q
diels-alder
A

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

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44
Q
diels-alder
A

Can serve as a dienophile in a Diels-Alder reaction, especially if the substituents (X) are electron-withdrawing groups

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45
Q

heat

ONLY reagant

A

When you see “heat” without any other reagents indicated, consider the possibility of a pericyclic reaction (cycloaddition, electrocyclic reaction, or a sigmatropic rearrangement)

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46
Q

hv

A

When you see this term (pronounced H-new), or “light”, without any other reagents indicated, consider the possibility of an electrocyclic reaction

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47
Q

Na2Cr2O7, H2SO4, H2O

benzylic rxn

A

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.

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48
Q
  1. KMnO4, H2O, heat
  2. H3O+

benzylic rxn

A

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.

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49
Q

NBS, heat

benzylic rxn

A

N-Bromosuccinimide. A reagent that is used for radical bromination at the benzylic position

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50
Q

H2O

benzylic rxn

A

Water is a weak nucleophile that can be used in an SN1 reaction with a benzylic halide

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51
Q

NaOH

benzylic rxn

A

Hydroxide is a strong nucleophile that can be used in an SN2 reaction with a primary benzylic halide.

52
Q

conc. H2SO4

with an oh

A

A strong acid that can be used to achieve acid-catalyzed dehydration to give an alkene

53
Q

NaOEt

with secondary or tertiary halides

A

Sodium ethoxide is a strong base that can be used to convert secondary or tertiary halides into alkenes (via an E2 process)

54
Q

 3 H2, 100 atm, 150ºC

benzene

A

Conditions for complete hydrogenation of benzene to give cyclohexane

55
Q

Na, CH3OH, NH3

with benzene ring

A

Reagents for a Birch reduction, which reduces a benzene ring to give a 1,4-cyclohexadiene ring.

56
Q

Br2, AlBr3 or FeBr3
bromination

with an aromatic ring

A

Installation of a bromine atom on an aromatic ring

57
Q

Br2
bromination

with a moderately or strongly activated aromatic ring

A

Installation of a bromine atom on a moderately or strongly activated aromatic ring

58
Q

Cl2, AlCl3 or FeCl3
chlorination

with an armoatic ring

A

Installation of a chlorine atom on an aromatic ring

59
Q

Cl2
chlorination

with a moderately or strongly activated aromatic

A

Installation of a chlorine atom on a moderately or strongly activated aromatic ring

60
Q

HNO3, H2SO4
nitration

with an aromatic ring

A

Installation of a nitro group on an aromatic ring. Cannot be performed if an amino group is already present on the aromatic ring

61
Q

Fuming H2SO4
sulfonation

with a benzene ring

A

Installation of a sulfonic acid group, often used as a blocking group

62
Q

Dilute H2SO4
desulfonation

A

Removes a sulfonic acid group

63
Q

RCl, AlCl3
Friedel-Crafts alkylation

with benzne

A

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
Q

friedel-crafts acylation

with an aromatic ring
A

Installation of an acyl group on an aromatic ring. This reaction cannot be performed on a moderately or strongly deactivated aromatic ring

65
Q
  1. Fe or Zn, HCl
  2. NaOH
    Reduction
A

Reduction of a nitro group to give an amino group

66
Q

Excess NBS
Benzylic bromination

A

Exhaustive bromination of the benzylic position

67
Q
  1. KMnO4, H2O, heat
  2. H3O+
    Benzylic oxidation
A

Oxidation of the benzylic position to give a carboxylic acid

68
Q

Zn(Hg), HCl, heat
Clemmensen reduction

with ketone or aldheyde carbonyl group

A

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
Q

NaOH
SNAr or elimination-addition

with aromatic

A

A strong nucleophile used in nucleophilic aromatic substitution reactions as well as elimination-addition reactions

70
Q

NaNH2
elimination-addition

A

A very strong base (and strong nucleophile) used in elimination-addition reactions

71
Q

H3O+
Hydrolysis of acetals imines, or enamines

A

Treating an acetal, an imine, or an enamine with H3O+ generates a carbonyl group via hydrolysis

72
Q

[H+], 2 ROH,
(− H2O)

with an aldehyde or ketone

A

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
Q

[H+], HOCH2CH2OH,
− H2O

with an aldehyde or ketone

A

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
Q

[H+], HSCH2CH2SH,,
(− H2O)

with an aldehyde or ketone

A

Cyclic thioacetal formation
Ethylene thioglycol can be used to convert an aldehyde or ketone into a cyclic thioacetal

75
Q

Raney nickel

with thioacetal

A

Desulfurization
Converts a thioacetal (or cyclic thioacetal) to an alkane.

76
Q

[H+], RNH2,
(− H2O)

with an aldehyde or ketone

A

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
Q

[H+], R2NH,
(− H2O)

with an aldehyde or ketone

A

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
Q

[H+], NH2OH,
(− H2O)

with an aldehyde or ketone

A

Oxime formation
Converts an aldehyde or ketone into an oxime.

79
Q

[H+], NH2NH2,
(− H2O)

with an aldehyde or ketone

A

Hydrazone formation
Converts an aldehyde or ketone into a hydrazone

80
Q

NaOH, H2O, heat

with a hydrazone

A

Wolff-Kishner reduction
Reduces a hydrazone to an alkane

81
Q
  1. LiAlH4
  2. H3O+

with an aldehyde or ketone

A

Reduces an aldehyde or ketone to an alcohol

82
Q
  1. RMgBr
  2. H3O+

with an aldehyde or ketone

A

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
Q

HCN, KCN

with an aldehyde or ketone

A

Converts an aldehyde or ketone into a cyanohydrin

84
Q
with an aldehyde or ketone
A

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
Q

Wittig reaction

with an aldehyde or ketone
A

A stabilized Wittig reagent that will react with an aldehyde or ketone to give the (E) alkene as the major product

86
Q

HWE reaction (Horner-Wadsworth- Emmons)

with an aldehyde or ketone
A

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
Q

RCO3H

with an aldehyde or ketone

A

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
Q

[H3O+], Br2

with a ketone (or aldehyde)

A

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
Q
  1. Br2, PBr3
  2. H2O

with a carboxylic acid

A

Hell-Volhard-Zelinsky reaction
These reagents can be used to install a bromine atom at the α position of a carboxylic acid.

90
Q

1.NaOH, Br2
2.H3O+

with a methyl ketone

A

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
Q

NaOH, H2O

with two equivalents of an aldehyde or ketone

A

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
Q

NaOH, H2O, heat

with two equivalents of an aldehyde or ketone

A

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
Q
  1. NaOEt
  2. H3O+

with two equivalents of an ester

A

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
Q
  1. LDA, -78ºC
  2. RX

with a ketone

A

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
Q
  1. NaH, 25ºC
  2. RX

with a ketone

A

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
Q

with NaOEt, alkyl halide, and H3O heat

A

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
Q

treatment with ethoxide, followed by an alkyl halide, followed by hydrolysis and decarboxylation with aqueous acid and heat.

A

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
Q
  1. R2CuLi
  2. H3O+

with a suitable Michael acceptor

A

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
Q

NaCN

with an alkyl halide

A

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
Q

1) Mg
2) CO2
3) H3O

with an alkyl halide

A

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
Q

1) LiAlH4
2) H3O+

with ketones, aldehydes, esters, or carboxylic acids

A

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
Q

pyridine

A

Pyridine is a weak base that is often used to neutralize for reactions that produce a strong acid as a by-product.

103
Q

SOCl2

with carboxylic acid or amide

A

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
Q

ROH

with an acid chloride or an acid anhydride

A

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
Q

NH3

with an acid chloride or an acid anhydride

A

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
Q

RNH2

with an acid chloride or an acid anhydride

A

Secondary amines are bases and nucleophiles. Excess amine can be used to convert an acid chloride or an acid anhydride into an amide

107
Q

1) xs RMgBr
2) H3O+

with an acid chloride, an acid anhydride, an ester, or a nitrile

A

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
Q

R2CuLi

with an acid chloride

A

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
Q

1) LiAl(OR)3H
2) H3O+

with an acid chloride or an acid anhydride

A

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
Q

1) DIBAH
2) H3O+

with an ester

A

Diisobutylaluminum hydride is a hydride reducing agent that will convert an ester into an aldehyde.

111
Q

H3O+

with an acid chloride, anhydride, esterm amide, or nitrile

A

Aqueous acid will cause hydrolysis of an acid chloride, an anhydride, an ester, an amide, or a nitrile to give a carboxylic acid.

112
Q

[H+], ROH

with carboxylic acid

A

Under acidic conditions, an alcohol will react with a carboxylic acid via a Fischer esterification, giving an ester

113
Q
  1. NaCN
  2. xs LiAlH4
  3. H2O

with an alkyl halide

A

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
Q
  1. SOCl2
  2. xs NH3
  3. xs LiAlH4
  4. H2O

with a carboxylic acid

A

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
Q
  1. Fe, H3O+
  2. NaOH

with an aryl nitro group

A

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
Q
  1. NaN3
  2. LiAlH4
  3. H2O

with an alkyl halide

A

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
Q
A

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
Q

NaBH3CN

reaction occurs between a ketone (or aldehyde) and an amine (or ammonia)

A

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
Q
with an amine
A

Acetylation
An amine will undergo acetylation (giving an amide) when treated with acetyl chloride.

120
Q
  1. Excess CH3I
  2. Ag2O, H2O, heat
A

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
Q

NaNO2, HCl

with a primary amine

A

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
Q

CuBr or CuCl or CuI or CuCN

with an an aryldiazonium salt

A

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
Q

HBF4

with an an aryldiazonium salt

A

Fluorination (Schiemann reaction)
When an aryldiazonium salt is treated with HBF4, the diazonium group is replaced with a fluorine atom

124
Q

H2O, heat

with an an aryldiazonium salt

A

Preparation of phenol
When an aryldiazonium salt is treated with water and heat, the diazonium group is replaced with an OH group

125
Q

H3PO2

with an an aryldiazonium salt

A

Reduction
When an aryldiazonium salt is treated with H3PO2, the diazonium group is replaced with a hydrogen atom

Organic Chemistry (CHE 3332) (2 decks)

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