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Carboxylic acid Flashcards

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1
Q

What is the functional group of a carboxylic acid?

A

carboxyl group (carbonyl group + hydroxyl group)

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2
Q

What is the general formula for an aliphatic carboxylic acid?

A

RCOOH

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3
Q

How do you name a carboxylic acid?

A

derived from the parent alkane by dropping the suffix -e and adding -oic acid

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4
Q

Why do you not need to give the carboxyl group a number?

A

Because it is understood to be carbon 1 because it is the highest priority functional group

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5
Q

How do you name a dicarboxylic acid?

A

Named as a -dioic acid and the longest chain contains both carboxyl carbons

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6
Q

Describe the polarity of carboxyl group (2 components)

A
  1. polar hydrophilic carboxyl group (incease solubility)

2. nonpolar hydrophobic hydrocarbonchain (decrease solubility)

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7
Q

Why do carboxylic acids have high boiling points?

A

Because they are associated by hydrogen bonding into dimers

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8
Q

Explain the increased acidity of carboxylic acids

A
  1. charge delocalization through resonance in a carboxylate anion relative to an alkoxide ion
  2. the electron-withdrawing inductive effect of the carbonyl group
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9
Q

pKa tells you the acidity of what?

A

The hydrogen atom in the molecule

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10
Q

pH tells you the acidity of what?

A

The solution

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11
Q

Write the equilibrium formula for acid HA with water

A

HA + H2O A- + H3O

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12
Q

Write the equilibrium formula for acid HA with water

A

HA + H2O A- + H3O

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13
Q

Why can all molecules be considered amphoteric?

A

Because they can always be protonated/deprotonated by a stronger acid/base

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14
Q

The pH of a solution depends on what two things?

A
  1. The concentration of the solution

2. The acid in question

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15
Q

Write the acidity constant Ka for the equilibrium reaction of an acid with water

A

Ka = [H3O][A-]/[AH}

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16
Q

What is the logarithmic form of the acidity constant?

A

pKa = -logKa

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17
Q

A stronger acid has a lower pKa or a higher pKa?

A

the lower the pKa the higher the Ka and the stronger the acid

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18
Q

Rearrange the expression for Ka to show that pKa is the pH at which an acid is exactly half dissociated

A
  1. Ka = [H3O][A-]/[AH]
  2. [H3O] = Ka * [AH]/[A-]
  3. pH = pKa - log [AH]/[A-]
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19
Q

At pH above the pKa, how does an acid exist?

A

Acid exists as A- in water and will be fairly soluble

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20
Q

At pH below the pKa, how does an acid exist?

A

Acid exists mostly as AH in water and will be less soluble

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21
Q

How are pKa and stability of conjugate base related?

A

More stable conjugate base has a higher Ka becuase they give up a proton more, and therefore have a lower pKa.

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22
Q

How are pKa and stability of conjugate base related?

A

More stable conjugate base has a higher Ka becuase they give up a proton more, and therefore have a lower pKa.

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23
Q

Explain the increased acidity of carboxylic acids compared to alcohols (2 components)

A
  1. charge delocalization through resonance in a carboxylate anion relative to an alkoxide ion
  2. electron withdrawing inductive effect of the carbonyl group
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24
Q

What are three ways to prepare a carboxylic acid?

A
  1. Oxidation of primary alcohols and aldehydes
  2. Treating a grignard reagent with carbon dioxide
  3. Treating a nitrile with water
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25
Q

Explain the problem with the reduction of carboxylic acids

A

Only LiAlH4 will reduce them. This means you can reduce other functional groups without worrying about carboxyl group.

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26
Q

Define fischer esterification

A

Prepration of an ester by treating a carboxylic acid with an alcohol in the presence of an acid catalyst such as a sulfuric acid

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27
Q

What is a powerful reagent for Fischer esterification and what product does it yield?

A

DIazomethane (CH2N2) gives a methyl ester in high yield.

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28
Q

How do you prepare an acid chloride from a carboxyl group?

A

Treatment with thionyl chloride

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29
Q

What is decarboxylation

A

Loss of CO2

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30
Q

What carboxylic acids undergo decarboxylation

A
  1. All carboxylic acids to some extent with enough heat

2. Carboxylic acids with a (second) carbonyl group Beta to the carboxyl group undergo undergo mild heating.

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31
Q

What is the IUPAC name of HCOOH

A

Methanoic acid

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32
Q

What is the common name of HCOOH

A

Formic acid

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33
Q

What is the IUPAC name of CH3COOH

A

Ethanoic acid

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34
Q

What is the common name of CH3COOH

A

Acetic acid

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35
Q

What is the IUPAC name of CH3CH2COOH

A

Propanoic acid

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36
Q

What is the common name of CH3CH2COOH

A

Propionic acid

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37
Q

What is the IUPAC name of CH3(CH2)2COOH

A

Butanoic acid

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38
Q

What is the common name of CH3(CH2)2COOH

A

Butyric acid

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39
Q

What is the IUPAC name of CH3(CH2)3COOH

A

Pentanoic acid

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40
Q

What is the common name of CH3(CH2)3COOH

A

Valeric acid

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41
Q

What is the common name of CH3(CH2)3COOH

A

Valeric acid

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42
Q

What is the IUPAC name for salicylic acid?

A

o-hydroxybenzoic acid

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43
Q

Electron-donating groups are what type of directing groups in EAS?

A

Ortho and para directing

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44
Q

Electron-withdrawing groups are what type of directing group in EAS?

A

Meta directing

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45
Q

What is the common name for HOOCCOOH

A

Oxalic acid (2 carbon dioic acid)

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46
Q

What is the common name for HOOC(CH2)COOH

A

Malonic acid (3 carbon dioic acid)

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47
Q

What is the common name for HOOC(CH2)2COOH

A

Succinic acid (4 carbon dioic acid)

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48
Q

What is the common name for HOOC(CH2)3COOH

A

Glutaric acid (5 carbon dioic acid)

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49
Q

What is the common name for HOOC(CH2)4COOH

A

Adipic acid (6 carbon dioic acid)

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50
Q

What is the common name for a carboxylic acid with a 12-carbon chain?

A

lauric acid

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51
Q

What is the common name for a carboxylic acid with a 14-carbon chain?

A

myristic acid

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52
Q

What is the common name for a carboxylic acid with a 16-carbon chain?

A

palmitic acid

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53
Q

What is the common name for a carboxylic acid with a 18-carbon chain?

A

stearic acid

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54
Q

How do you name an acid chloride?

A

-ic acid replaced by -yl chloride

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55
Q

How do you name an amide?

A

-ic/-oic acid replaced by -amide

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56
Q

How do you name an ester?

A
  1. -ic acid replaced by -ate

2. precede name by alkyl or aryl group bonded to oxygen (R’)

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57
Q

How do you name an anhydride?

A

acid replaced by anhydride

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58
Q

How do you name the salt of a carboxylic acid?

A
  1. Replace the -ic/-oic acid with -ate

2. Precede name by name of counterion

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59
Q

How do you name an anhydride if the acyl groups are different?

A

List the groups in alphabetical order

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60
Q

What is an acyl group?

A

R-CO -

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61
Q

What are the five most important carboxylic acid derivatives?

A
  1. acid halides
  2. acid anhydrides
  3. esters
  4. amides
  5. nitriles
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62
Q

What are acid halides?

A

Acyl group bonded to a halogen

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63
Q

What are acid anhydrides?

A

Two acyl groups bonded to an O atom

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64
Q

What are esters?

A

Acyl group bonded to an -OR group

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65
Q

What are amides?

A

Acyl group bonded to an N atom

66
Q

What are nitriles?

A

A cyano group bonded to a carbon

67
Q

What are lactones?

A

Cyclic esters in which the acyl carbon and O atom are part of the ring

68
Q

What are lactams?

A

cyclic amides in which the acyl carbon and the N atom are part of the ring

69
Q

What are imides?

A

Two acyl groups attached to the same N atom

70
Q

How do you name an lactone??

A
  1. IUPAC: Count number of carbons from carboxyl carbon to the carbon that is bonded to Sp3 oxygen, drop -ic acid and name it -olide
  2. Common name: count carbons the same way, drop -ic acid and name it -olactone, indicate substitutions with greek letters.
71
Q

How do you name an lactone??

A
  1. IUPAC: Count number of carbons from carboxyl carbon to the carbon that is bonded to Sp3 oxygen (count around the ring), drop -ic acid and name it -olide
  2. Common name: count carbons the same way, drop -ic acid and name it -olactone, indicate substitutions with greek letters.
72
Q

How do you name a lactam?

A

IUPAC: Count number of carbons from carboxyl carbon to the carbon that is bonded to N (count around the ring) drop -ic acid and name it -lactam

73
Q

How do you name an imide?

A

Similar to an anhydride; name acyl group as a carboxylic acid derivative; drop -ic/-oic acid and add amide.(alphabetical order if different) and

74
Q

How do you indicate substitutions on an amide?

A

Indicate substitutions on N-atom in the name by preceding the group with N (i.e. N-methyl)

75
Q

Rank Carboxylic acid, acid halides, acid anhydrides, esters, amides and nitriles by their solubility from least soluble to most soluble

A
  1. Ester
  2. Nitrile
  3. Amide
  4. Carboxylic acid
  5. Acid halides and acid anhydrides react with water (hydrolysis)
76
Q

Rank Carboxylic acid, acid halides, acid anhydrides, esters, amides and nitriles by their solubility from least soluble to most soluble

A
  1. Ester
  2. Nitrile
  3. Amide
  4. Carboxylic acid
  5. Acid halides and acid anhydrides react with water (hydrolysis)
77
Q

Rank Carboxylic acid, acid halides, acid anhydrides, esters, amides and nitriles by their boiling point from least to highest boiling

A
  1. Nitrile
    * *2. Ester (similar to hydrocarbons)
  2. Acid halide
  3. Anhydride
    * *5. Carboxylic acid (above 10 carbons are solid at room temp)
    * *6. Amide
78
Q

Rank Carboxylic acid, acid halides, acid anhydrides, esters, amides and nitriles by their boiling point from least to highest boiling

A
  1. Nitrile
    * *2. Ester (similar to hydrocarbons)
  2. Acid halide
  3. Anhydride
    * *5. Carboxylic acid (above 10 carbons are solid at room temp)
    * *6. Amide
79
Q

What are the two steps in nucleophilic acyl substitution?

A
  1. A strong nucleophile adds directly to acyl carbon, breaking C=O pi bond and creating a tetrahedral addition intermediate (a weaker nucleophile can be catalyzed by acid)
  2. Tetrahedral intermediate collapses by losing a leaving group and reforming the C-O pi bond.
80
Q

Rank the leaving group ability of amides, esters, anhydrides and acid halides from best leaving group to worst

A
  1. Acid halides
  2. Anhydride
  3. Ester
  4. Amide
81
Q

What are two factors influencing the relative reaction rates of the carboxylic acid derivatives to acyl substitution?

A
  1. Relative leaving group ability

2. Relative resonance stabilization

82
Q

How does resonance stabilization affect rate of acyl substitution?

A

If a molecule is more stabilized by resonance it is less likely to react (the partial positive charge is removed from the carbon).

83
Q

Rank the relative resonance stabilization from least stabilized to best

A
  1. Acid halide
  2. Anhydride
  3. Ester
  4. Amide
84
Q

Rank the relative resonance stabilization from least stabilized to best

A
  1. Acid halide
  2. Anhydride
  3. Ester
  4. Amide
85
Q

What does catalysis refer to in carboxylic acid chemistry?

A

When converting between functional groups, acid halide and anhydride are reactive enough that common nucleophiles will react directly. But esters and amides require acid or base catalysis.

86
Q

What is the theory behind base catalysis?

A

Base is used to increase nucleophilicity by converting a neutral nucleophile to an anionic nucleophile

87
Q

What is the theory behind acid catalysis? (2 components)

A

Acid is used to (1) increase positive charge on carbonyl carbon by protonating carbonyl oxygen OR (2) used to protonate a leaving group to allow it to leave as a stable molecule

88
Q

What is the theory behind acid catalysis? (2 components)

A

Acid is used to (1) increase positive charge on carbonyl carbon by protonating carbonyl oxygen OR (2) used to protonate a leaving group to allow it to leave as a stable molecule

89
Q

What is the mechanism for Fischer esterification

A
  1. Protonate carbonyl group
  2. Make a new bond between carboxyl carbon and alcohol. Deprotonate alcohol
  3. Protonate carboxyl group. Leave as stable water.
  4. Deprotonate alcohol to restore original carbonyl group.
90
Q

What is the mechanism for Fischer esterification

A
  1. Protonate carbonyl group
  2. Make a new bond between carboxyl carbon and alcohol. Deprotonate alcohol
  3. Protonate carboxyl group. Leave as stable water.
  4. Deprotonate alcohol to restore original carbonyl group.
91
Q

What are four (4) carboxylic fatty acids?

A
  1. Lauric (12)
  2. Myristic (14)
  3. Palmitic (16)
  4. Stearic (18)
92
Q

What are four oxidation reactions to prepare a carboxylic acid?

A
  1. Oxidation of arene side chain
  2. Oxidation of primary alcohols
  3. Oxidation of aldehydes
  4. Oxidative cleavage (tautomerization) of alkynes
93
Q

How do you prepare a carboxylic acid by oxidation of arene side chain?

A

Hot KMnO4, H2O will oxidize all benzylic carbons with at least one hydrogen to carboxyl groups.

94
Q

How do you prepare a carboxylic acid by oxidation of primary alcohols?

A

Chromic acid

95
Q

How do you prepare a carboxylic acid by oxidation of aldehydes?

A

Tollen’s reagent (Ag+ in NH4OH)

96
Q

How do you prepare a carbxylic acid by oxidative cleavage?

A

Hg2+, H2SO4 or

1) BH3 2)H2O2, NaOH

97
Q

What are two unique synthetic methods for a carboxylic acid and what is unique about them?

A
  1. Hydrolysis of nitriles
  2. Carboxylation of organometallic reagents

Both methods increase chain size by 1.

98
Q

Explain the hydrolysis of nitriles method of preparing a carboxylic acid

A
  1. Sn2 reaction of CN- with an alkyl halide

2. Nitrile is put with water; similar addition of water across triple bond and tautomerization. NH4+ leaves

99
Q

Explain the carboxylation of organometallic reagents method of preparing a carboxylic acid

A

Grignard reagent is treated with CO2 and H3O+. Results in a carboxyl carbon being added to the alkyl group of grignard reagent.

100
Q

Explain the carboxylation of organometallic reagents method of preparing a carboxylic acid

A

Grignard reagent is treated with CO2 and H3O+. Results in a carboxyl carbon being added to the alkyl group of grignard reagent.

101
Q

What reagents are used to convert a carboxylic acid into an ester?

A

Acid and R-OH

102
Q

What reagents are used to convert a carboxylic acid into an acid chloride?

A

SOCl2

103
Q

What reagents are used to convert a carboxylic acid into an amide?

A

NH3 (or a derivative)

104
Q

What reagents are used to convert a carboxylic acid into an anhydride?

A

An acid chloride and carboxylic acid.

105
Q

How do you predict the product of the reaction between an acid chloride and a carboxylic acid to form an anhydride?

A

Take both acyl groups and bond them to a common -O-.

106
Q

Predict the product of an acid chloride reacting with water.

A

Cl is substituted for -OH.

107
Q

How do you convert an acid chloride to an aldehyde?

A

LiAlH(Ot-Bu)3

108
Q

How do you convert an acid chloride to an ester?

A

R-OH

109
Q

How do you convert an acid chloride to an amide?

A

React with ammonia or primary/secondary amine (mono/disubstituted ammonia)

110
Q

How do you convert an acid chloride to a ketone?

A

Organocuprate reagent

111
Q

How do you convert an acid anhydride to a carboxylic acid?

A

Acid anhydrides react with water to form carboxylic acids.

112
Q

How do you convert an acid anhydride to an ester?

A

Acid anhydride + R-OH —> Ester and Carboxylic acid

113
Q

Predict the product of an acid anhydride with an alcohol.

A

Break the bond between the two acyl groups; attach hydrogen to one of the oxygens (carboxylic acid product) and the alkyl group on the alcohol to the other acyl group (ester product).

114
Q

How do you convert an acid anhydride to an amide?

A

Acid anhydrides react with primary and secondary amines to form amides.

115
Q

Predict the products of an acid anhydride with an alcohol.

A

Break the bond between the two acyl groups; attach hydrogen to the carbon containing the oxygen (carboxylic acid product) and the alkoxy group from the alcohol to the other acyl group (ester product).

116
Q

How do you convert an acid anhydride to an amide?

A

Acid anhydrides react with primary and secondary amines to form amides.

117
Q

Predict the products of an acid anhydride with a primary or secondary amine.

A

Break the bond between the two acyl groups; attach amine minus one hydrogen to the carboxyl carbon (amide product) and form a salt with the protonated amine and the remaining carboxylate ion

118
Q

How do you convert an acid anhydride to an ester?

A

Acid anhydride + R-OH —>(Pyridine) Ester and Carboxylic acid

119
Q

Predict the products of an acid anhydride with a primary or secondary amine.

A

Break the bond between the two acyl groups; attach amine minus one hydrogen to the carboxyl carbon (amide product) and form a salt with the protonated amine and the remaining carboxylate ion

120
Q

What is acid catalyzed hydrolysis of an ester?

A

Esters can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a catalytic amount of acid.

121
Q

Predict the products of an ester in acid catalyzed hydrolysis

A

The acyl alkyl group forms a carboxylic acid and the ester alkyl group forms an alcohol.

122
Q

How do you prepare a tertiary alcohol from an ester?

A

Addition of grignard reagents converts esters to tertiary alcohols.

123
Q

Predict the products of grignard addition to an ester

A

Alkyl group from grignard reagent adds twice to ester. The original ester -OR group is converted to an alcohol by addition of H.

124
Q

How do you prepare a primary alcohol from an ester?

A

Esters can be converted to primary alcohols using LiAlH4

125
Q

Predict the products of an ester in LiAlH4

A
  1. Remove the carbonyl oxygen and convert -OR to -OH to get primary alcohol product.
  2. Original ester -OR group is protonated to form additional alcohol product.
126
Q

How do you prepare an amide from an ester? (2 methods)

A
  1. Liquid ammonia at -70 degrees Celsius forms an amide and an alcohol.
  2. aqueous ammonia at -10 degrees Celsius for one hour
127
Q

Predict the products of an ester in liquid or aqueous ammonia

A

substitute -OR on ester for -NH2 and protonate the original ester -OR to form an alcohol.

128
Q

Predict the products of an ester in liquid or aqueous ammonia

A

substitute -OR on ester for -NH2 and protonate the original ester -OR to form an alcohol.

129
Q

How do you prepare an aldehyde from an ester?

A

Esters can be converted to aldehydes using diisobutylaluminum hydride (DIBAH).

130
Q

Predict the products of an ester in DIBAH

A

substitute the -OR on ester for an H to form aldehyde product. protonate original ester -OR to form an alcohol product.

131
Q

What is transesterification?

A

When one ester is converted into another by an exchange of alkoxy groups.

132
Q

What are the reaction conditions for transesterification?

A

The most common method is a large excess of alcohol with an acid catalyst such as H2SO4.

133
Q

Predict the products for RCOOR’ + R’‘-OH

A

RCOOR’’ + R’-OH (exchange alkoxy groups)

134
Q

What is saponification of an ester?

A

Hydrolysis (ester -> carboxylic acid + alcohol) using water and NaOH (basic)

135
Q

Predict the products of an ester in H2O/NaOH

A

The products are a carboxylate ion (carboxylic acid is deprotonated because of basic conditions) and an alcohol form from the ester -OR group.

136
Q

Predict the products of an ester in H2O/NaOH

A

The products are a carboxylate ion (carboxylic acid is deprotonated because of basic conditions) and an alcohol form from the ester -OR group.

137
Q

How do you prepare an amide from a nitrile?

A

Nitriles can be converted to amides when acid catalyzed by HCl at 40 degrees celsius.

138
Q

How do you prepare a nitrile from a primary amide?

A

primary amides can be converted to nitriles by reaction by dehydration with thionyl chloride (SOCl2)

139
Q

Predict the products of a primary amide in SOCl2

A

Replace CONH2 carbon of primary amide with CtriplebondN

140
Q

How do you prepare an amine from an amide?

A

Amides can be converted to 1°, 2° or 3° amines using LiAlH4.

141
Q

Predict the products of a primary, secondary or tertiary amine in LiAlH4

A

Remove the carbonyl oxygen.

142
Q

What are the two types of hydrolysis of amides?

A
  1. Hydrolysis under acidic conditions

2. Hydrolysis under basic conditions

143
Q

What are the products when amides are hydrolyzed under acidic conditions (HCl)?

A

A carboxylic acid and an ammonium chloride.

144
Q

What are the products when amides are hydrolyzed under alkaline conditions (OH-)?

A

Sodium carboxylate and ammonia.

145
Q

What are the two types of hydrolysis of amides?

A

Both require severe conditions (heat):

  1. Hydrolysis under acidic conditions
  2. Hydrolysis under basic conditions
146
Q

What are the products when amides are hydrolyzed under alkaline conditions (OH-)?

A

Sodium carboxylate and ammonia.

147
Q

How can you form an imide?

A

A difunctional molecule containing an amide and a carboxylic acid can dehydrate to form an imide with heat.

148
Q

Predict the product of a amide/carboxylic acid molecule forming an imide.

A

Remove hydroxyl and a hydrogen from the nitrogen and create a new bond between nitrogen and the other acyl carbon.

149
Q

Predict the product of a amide/carboxylic acid molecule forming an imide.

A

Remove hydroxyl and a hydrogen from the nitrogen and create a new bond between nitrogen and the other acyl carbon.

150
Q

What is the product of Claisen condensation?

A

A beta-ketoester.

151
Q

What are the reactants and the reaction conditions for Claisen condensation?

A

Two molecules of an ester with a strong nonaqueous base like sodium ethoxide in ethanol.

152
Q

Describe how the Claisen reaction works (3 steps)

A
  1. A strong base removes an alpha-hydrogen from an ester to form an enolate ion which is a nucleophile for addition to an ester.
  2. The -OR (alkoxy) of the ester leaves as a strong base then deprotonates the carbon tethered between carbonyl carbons forming a weak base (enolate ion) and an alcohol.
  3. Mild acid is added to protonate enolate ion to give the beta-ketoester.
153
Q

Distinguish between Amine, Amide, Imine, Imide

A
  • ides are acyl group containing compounds:
    1. Amine: Ammonia derivative
    2. Amide: Carboxylic acid derivative, -OH replaced by -NH2
    3. Imine: C=N
    4. Imide: two acyl groups bound to nitrogen
154
Q

Explain why the reaction of an acid chloride with ammonia to form an amide is spontaneous (2 components)

A

The acid chloride is a strong leaving group than the NH2 and the amide is more stable than the acid chloride because of resonance stabilization.

155
Q

What are the reagents to halogenate an aromatic ring?

A

X2, FeX3

156
Q

What are the reagents for friedal crafts acylation

A

RCOCl + AlCl3

157
Q

Predict the products of an acid anhydride with a primary or secondary amine.

A

Break the bond between the two acyl groups; attach amine minus one hydrogen to the carboxyl carbon (amide product) and form a salt with the protonated amine and the remaining carboxylate ion

158
Q

Explain why the reaction of an acid chloride with ammonia to form an amide is spontaneous/favorable (2 components)

A

The acid chloride is a strong leaving group than the NH2 and the amide is more stable than the acid chloride because of resonance stabilization.

159
Q

What are the reagents for friedal crafts acylation

A

RCOCl + AlCl3

160
Q

Explain why Thioesters are more reactive to nucleophilic acyl substitution than ordinary carboxylic esters

A

Weaker bases are better leaving groups and RS- (thiolate) is a weaker base than RO- (alkoxide)

161
Q

Predict the product for benzoic acid with sodium bicarbonate.

A

Sodium benzoate and carbonic acid (strong acid makes weaker acid)

162
Q

Predict the product for benzoic acid with sodium bicarbonate.

A

Sodium benzoate and carbonic acid (strong acid makes weaker acid)

Organic Chemistry (9 decks)

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