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Organic Chemistry > Midterm Review. > Flashcards

Midterm Review. Flashcards

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1
Q

What is an acid chloride?

A
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2
Q

What are more reactive, aldehydes or acids?

A

Aldehydes are more reactive than acids.

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3
Q

How are acid chlorides generated?

A

The reaction of carboxylic acids with thionyl chloride (SOCl2) generates acid chlorides.

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4
Q

Why are weaker reducing agents more suitable for forming acid chlorides to aldehydes.

A

Strong reducing agents like LiAlH4 still reduce acid chlorides all the way to primary alcohols. Milder reducing agents like lithium aluminum tri(tbutoxy)hydride (LiAlH4) can selectively reduce acid chlorides to aldehydes.

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5
Q

How can an acid chloride be reduced to a ketone using a LiAlH4?

A

Acid chloride + LiAlH4 gives an aldehyde. Aldehyde + Grignard reagent gives a ketones.

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6
Q

How can an acid chloride be reduced to a ketone using only a Grignard reagent or organolithium reagents?

A

Grignard reagent and acid chloride react. Chlorine is removed from the carbon and the new carbon chain takes its place.

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7
Q

What is an organolithium reagent made up of?

A

2R-Li + CuI = 2R-Cu-Li + Li-I.

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8
Q

What is the Gilman reagent?

A

R2-Cu-Li. Lithium dialkylcuprate.

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9
Q

What is the Swern reaction used for?

A

The oxidation of alcohols.

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10
Q

A primary alcohol is oxidised to what?

A

A primary alcohol is oxidised to an aldehyde, then to a carboxylic acid if oxidation is allowed to continue.

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11
Q

How can oxidation be stopped at the aldehyde stage?

A

By using a weak oxidising agent such as PPT or the Swern oxidation.

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12
Q

A secondary alcohol is oxidised to what?

A

A ketone.

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13
Q

A tertiary alcohol is oxidised to what?

A

No reaction occurs.

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14
Q

How can you recognise the Swern reaction?

A

DMSO is used as the oxidising agent along with oxalyl chloride and pyridine.

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15
Q

Why is the Swern reaction a convenient reaction?

A

The by-products of this reaction can be easily separated from the products, making this a convenient reaction.

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16
Q

Give a brief overview of the Swern reaction?

A

Alcohol + DMSO + Oxalyl chloride = A ketone or an aldehyde + dimethyl sulfide.

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17
Q

What is the mechanism of the Swern reaction?

A

DMSO attacks oxalyl chloride. Then the alcohol is attacked and the H is removed and a double bond is formed.

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18
Q

What is oxalyl choride?

A

O O II II Cl-C-C-Cl (COCl)2

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19
Q

What is the 1st step of the Swern reaction?

A

Reagents react then attack the alcohol.

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20
Q

What are the 3 Swern reagents?

A
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21
Q

Is a tosylate a good leaving group?

A

Yes.

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22
Q

What can attack C-OTS?

A

Any nucleophile.

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23
Q

When a nucleophile attacks a C-OTS, what kind of reaction takes place?

A

Elimination or substitution.

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24
Q

R-OTS + OH. Gives what?

A

R-OH + -OTS.

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25
Q

R-OTS + C=N. Gives what?

A

R-C(TRIPLE BOND)N + -OTS.

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26
Q

R-OTS + BR-. Gives what?

A

R-BR + -OTS.

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27
Q

R-OTS + R-O-. Gives what?

A

R-O-R + -OTS.

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28
Q

R-OTS + :NH3. Gives what?

A

R-NH3+ + -OTS.

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29
Q

R-OTS + LiAlH4. Gives what?

A

R-H + -OTS.

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30
Q

Why is a tosylate such a stable anion?

A

The tosylate ion is a particularly stable anion, with its negative charge delocalized over three oxygen atoms.

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31
Q

What is the Jones reagent?

A

Chromic acid in acetone.

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32
Q

What is the Collins reagent?

A

Cr2O3 in pyridine.

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33
Q

When alcohols become alkanes, how many steps are in the process?

A

Alcohols to alkanes is a 2 step process.

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34
Q

Name the 2 ways that alcohols can become alkanes?

A
  1. Alcohol + H2SO4 = Alkene. Alkene + H2 and PD = Alkane. 2. Alcohol + TsCl = Tosylate. Tosylate + LiAlH4 gives an alkane.
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35
Q

What kind of reaction takes place when H2SO4 is added to an alcohol?

A

An E2 reaction.

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36
Q

What is oxidation?

A

The gain of oxygen or loss of hydrogen.

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37
Q

What is reduction?

A

The gain of hydrogen or loss of oxygen.

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38
Q

What is the structure of PCC?

A
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39
Q

What can ethylene glycol be oxidised to?

A

Oxalic acid.

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40
Q

What does methanol oxidise to?

A

Formaldehyde then formic acid.

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41
Q

What does ethylene glycol look like?

A
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42
Q

What does oxalic acid look like?

A
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43
Q

What are the reactions for the oxidation of methanol and ethylene glycol?

A
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44
Q

What is the treatment for methanol poisoning?

A

Excess alcohol.

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45
Q

How does excess ethanol treat methanol poisoning?

A

Ethanol oxidises to acetaldehyde then acetic acid.

Acetic acid reats with the poison.

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46
Q

List the order of alcohols that are most reactive with the Lucas reagent?

A

Tertiary = Most reactive.

Secondary.

Primary = Least reactive.

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47
Q

How does the Lucas reagent react with a primary alcohol?

A

SN2 reaction.

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48
Q

How does the Lucas reagent react with a scondary or tertiary alcohol?

A

SN1 reaction.

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49
Q

What is the Lucas reagent?

A

HCl + ZnCl2.

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50
Q

What is the SN1 reaction with the Lucas reagent?

A
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51
Q

What is the SN2 reaction with the Lucas reagent?

A
52
Q

What is the Fischer esterification?

A

It is the reaction of a carboxylic acid with an alcohol to make an ester.

53
Q

What is the mechanism of the Fischer esterification?

A
54
Q

What reaction is an alcohol + an acyl chloride?

A

Esterification reaction

55
Q

What is the mechanism of an alcohol + an acyl chloride?

A
56
Q

What is the iodoform reaction?

A
57
Q

What is are the inorganic products from the iodoform reaction on an aldehyde?

A

5I- and 5H2O.

58
Q

What is are the inorganic products from the iodoform reaction on a ketone?

A

3I- and 3H2O.

59
Q

What is are the organic products from the iodoform reaction on an aldehyde?

A

CHI3 and HCOO-.

60
Q

What is are the organic products from the iodoform reaction on a ketone?

A

C5H11COO- and CHI3.

61
Q

What test can distinguish 2 propanol from 1 propanol?

A

The iodoform test.

62
Q

What is the Williamson ether synthesis?

A

This method involves an SN2 attack of the alkoxide on an unhindered primary halide or tosylate.

63
Q

What is the best reagent for a Williamson Ether synthesis?

A

Pimary alkyl halides and methyl groups.

64
Q

What is the mechanism of the Williamson ether synthesis?

A
65
Q

How is the alkoxide for the Williamson ether synthesis made?

A

By reacting Na, K or NaH with the alcohol.

66
Q

LiAlH4 is a good source of what?

A

Hydride (H-) ions.

67
Q

LiAlH4 is a good for what reaction?

A

Reduction.

68
Q

To make an aldehyde from an acid chloride what reducing agent is used?

A

Lithium aluminum tri(t-butoxy)hydride is a milder reducing agent that reacts faster with acid chlorides than with aldehydes.

69
Q

What is the mechanism of an acid chloride to an aldehyde?

A
70
Q

Grignard reagents with aldehydes form what?

A

Secondary alcohol.

71
Q

Grignard reagents with ketones form what?

A

Tertiary alcohols.

72
Q

Grignard reagents with CO2 form what?

A

Reaction with carbon dioxide yields a carboxylic acid one carbon longer than Grignard reagent!

73
Q

Grignard reagent + an ester, yields what?

A

Reaction 1. A ketone.

Reaction 2. A teritary alcohol.

74
Q

List the activating groups from most reactive to least reactive?

A

-O-.

R
I
-N-R.

  • O-H.
  • O-R.

H O
I II
-N-C-R

-R (No lone pairs.)

75
Q

List the activating compounds from most reactive to least reactive?

A

Phenoxides.

Anilines.

Phenols.

Phenyl ethers.

Anilides.

Alkyl benzenes.

76
Q

List the deactivating groups?

A
  • NO2. (Nitro.)
  • SO3H. (Sulfonic acid.)
  • C TRIPLE BOND N. (Cyano.)

Ketone or aldehyde.

Ester.

Quaternary ammonium.

77
Q

Activating groups form what orientation?

A

Ortho or para?

78
Q

Deactivating groups form what formation?

A

Meta.

79
Q

Which deactivators form ortho or para orientation?

A

Halogens.

80
Q

What is an N-Substituted Imine?

A
81
Q

What is an N substituted enamine?

A
82
Q

Do activators speed up or slow donw reactions?

A

Speed them up.

83
Q

Is a methyl group on a benzene ring an activator or a deactivator?

A

An activator.

84
Q

When reducing and acid chloride to an alcohol, what is the reducing agent?

A

LiAlH4.

85
Q

What are the steps when making an alcohol from an acid chloride?

A

Reduce acid chloride to aldehyde.

Oxidise aldehyde to alcohol.

86
Q

What kind of alcohol does an acid chloride give?

A

A primary alcohol.

87
Q

What enzyme turns ethanol into ethanal?

A

Alcohol dehydrogenase.

88
Q

What is the enzyme for pyruvate to lactic acid?

A

Lactic acid dehydrogenase.

89
Q

Lactic acid to pyruvic acid is what kind of reaction?

A

Oxidation.

90
Q

What turns alcohol into acetaldehyde?

A

Alcohol dehydrogenase.

91
Q

What turns acetaldehyde into acetic or ethanoic acid?

A

Aldehyde dehydrogenase.

92
Q

What is the enzyme that converts pyruvate to lactic acid?

A

Lactic acid dehydrogenase.

93
Q

What is the co enzyme that turns pyruvate to lactic acid?

A

NADH+ and H+.

94
Q

What is the oxidising agent when oxidising alcohol?

A

NAD+.

95
Q

What inhibits aldehyde dehydrogenase?

A

Disulfiram.

96
Q

How do you turn an alkyl chloride into a nitrile?

A

Add CN-. E.g. NaCN.

97
Q

How do you turn a nitrile into a ketone?

A

Add H30+ and the oxygen will take the place of the N-H.

98
Q

Describe the reaction of synthesisng a nitrile from an alkyl chloride then a ketone from the nitrile?

A
99
Q

When making a ketone from a nitrile, what attacks the C to N bond?

A

A grignard or organolithium reagent.

100
Q

When making a nitrile from alkyl chloride, how many carbons does the chain increase by?

A

1.

101
Q

What happens when you react a phenol with NaOH and HCl?

A

NaOH removes the H from the OH leaving O-.

The O- attacks the H-Cl.

Alcohol reforms.

102
Q

A ketone or aldehyde + NH3 gives what?

A

The nitrogen loses 2 hydrogens and forms a double bond to the C in place of the oxygen.

C=NH.

103
Q

A ketone or aldehyde + a primary amine (NH2-CH3) gives what?

A

C=N-CH3.

104
Q

A ketone or aldehyde + a hydroxyl amine (NH2-OH) gives what?

A

C=N-OH.

105
Q

A ketone or aldehyde + a phenylhydrazine gives what?

A
106
Q

A ketone or aldehyde + a secondary amine (R-NH-R) gives what?

A
107
Q

A ketone or aldehyde + an alcohol gives what?

A

A hemiacetal or hemiketal.

108
Q

A ketone or aldehyde + alcohol, what is formed?

A

A ketal or acteal.

109
Q

A ketone or aldehyde + HCN and water, what is formed?

A

A cyanohydrin is formed.

The water then adds an H to the oxygen.

110
Q

How do you convert toluene to para chloro benzoic acid?

A

Tolunene + KMnO4 + NaOH + heat = Benzoic acid.

111
Q

What are ortho para and meta directors?

A
112
Q

Which donors are ortho, para or meta directing?

A
113
Q

What is the Wittig reaction used for?

A

Making alkenes.

114
Q

What does the Wittig reaction use?

A

Phosphorous.

115
Q

What is the Wittig reaction mechanism?

A
116
Q

What reagents are used for the bromination of benzene?

A

Br2 + FeBr3.

117
Q

What reagents are used for the chlorination of benzene?

A

Cl2 + AlCl3.

118
Q

What reagents are used for the iodination of benzene?

A

H+ + HNO3 + ½ I2 I+ + NO2 + H2O

119
Q

What is the mechanism for the halogenation of benzene?

A
120
Q

What is the electrophile for sulfonation?

A

SO3.

121
Q

What is the electrophile for nitration?

A

NO2+.

122
Q

What is the electrophile for halogenation?

A

FeBr3 FeCl3.

123
Q

What is the electrophile for alkylation?

A

CH3-CH2-Cl.

124
Q

What is the electrophile for acylation?

A

CH3-CO-Cl.

125
Q

How can you tell if the compound is aromatic, anti aromatic or not aromatic?

A

Organic Chemistry (9 decks)

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