Brainscape's Knowledge GenomeTM


Top Flashcards (Certified)
All Flashcards

Organic Chemistry > Midterm Review. > Flashcards

Midterm Review. Flashcards

1
Q

What is an acid chloride?

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

What are more reactive, aldehydes or acids?

A

Aldehydes are more reactive than acids.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

How are acid chlorides generated?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

What is an organolithium reagent made up of?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

What is the Gilman reagent?

A

R2-Cu-Li. Lithium dialkylcuprate.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

What is the Swern reaction used for?

A

The oxidation of alcohols.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

A secondary alcohol is oxidised to what?

A

A ketone.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

A tertiary alcohol is oxidised to what?

A

No reaction occurs.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

How can you recognise the Swern reaction?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Give a brief overview of the Swern reaction?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

What is oxalyl choride?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

What is the 1st step of the Swern reaction?

A

Reagents react then attack the alcohol.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

What are the 3 Swern reagents?

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Is a tosylate a good leaving group?

A

Yes.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

What can attack C-OTS?

A

Any nucleophile.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

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

A

Elimination or substitution.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

R-OTS + OH. Gives what?

A

R-OH + -OTS.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
R-OTS + C=N. Gives what?
R-C(TRIPLE BOND)N + -OTS.
26
R-OTS + BR-. Gives what?
R-BR + -OTS.
27
R-OTS + R-O-. Gives what?
R-O-R + -OTS.
28
R-OTS + :NH3. Gives what?
R-NH3+ + -OTS.
29
R-OTS + LiAlH4. Gives what?
R-H + -OTS.
30
Why is a tosylate such a stable anion?
The tosylate ion is a particularly stable anion, with its negative charge delocalized over three oxygen atoms.
31
What is the Jones reagent?
Chromic acid in acetone.
32
What is the Collins reagent?
Cr2O3 in pyridine.
33
When alcohols become alkanes, how many steps are in the process?
Alcohols to alkanes is a 2 step process.
34
Name the 2 ways that alcohols can become alkanes?
1. Alcohol + H2SO4 = Alkene. Alkene + H2 and PD = Alkane. 2. Alcohol + TsCl = Tosylate. Tosylate + LiAlH4 gives an alkane.
35
What kind of reaction takes place when H2SO4 is added to an alcohol?
An E2 reaction.
36
What is oxidation?
The gain of oxygen or loss of hydrogen.
37
What is reduction?
The gain of hydrogen or loss of oxygen.
38
What is the structure of PCC?
39
What can ethylene glycol be oxidised to?
Oxalic acid.
40
What does methanol oxidise to?
Formaldehyde then formic acid.
41
What does ethylene glycol look like?
42
What does oxalic acid look like?
43
What are the reactions for the oxidation of methanol and ethylene glycol?
44
What is the treatment for methanol poisoning?
Excess alcohol.
45
How does excess ethanol treat methanol poisoning?
Ethanol oxidises to acetaldehyde then acetic acid. Acetic acid reats with the poison.
46
List the order of alcohols that are most reactive with the Lucas reagent?
Tertiary = Most reactive. Secondary. Primary = Least reactive.
47
How does the Lucas reagent react with a primary alcohol?
SN2 reaction.
48
How does the Lucas reagent react with a scondary or tertiary alcohol?
SN1 reaction.
49
What is the Lucas reagent?
HCl + ZnCl2.
50
What is the SN1 reaction with the Lucas reagent?
51
What is the SN2 reaction with the Lucas reagent?
52
What is the Fischer esterification?
It is the reaction of a carboxylic acid with an alcohol to make an ester.
53
What is the mechanism of the Fischer esterification?
54
What reaction is an alcohol + an acyl chloride?
Esterification reaction
55
What is the mechanism of an alcohol + an acyl chloride?
56
What is the iodoform reaction?
57
What is are the inorganic products from the iodoform reaction on an aldehyde?
5I- and 5H2O.
58
What is are the inorganic products from the iodoform reaction on a ketone?
3I- and 3H2O.
59
What is are the organic products from the iodoform reaction on an aldehyde?
CHI3 and HCOO-.
60
What is are the organic products from the iodoform reaction on a ketone?
C5H11COO- and CHI3.
61
What test can distinguish 2 propanol from 1 propanol?
The iodoform test.
62
What is the Williamson ether synthesis?
This method involves an SN2 attack of the alkoxide on an unhindered primary halide or tosylate.
63
What is the best reagent for a Williamson Ether synthesis?
Pimary alkyl halides and methyl groups.
64
What is the mechanism of the Williamson ether synthesis?
65
How is the alkoxide for the Williamson ether synthesis made?
By reacting Na, K or NaH with the alcohol.
66
LiAlH4 is a good source of what?
Hydride (H-) ions.
67
LiAlH4 is a good for what reaction?
Reduction.
68
To make an aldehyde from an acid chloride what reducing agent is used?
Lithium aluminum tri(t-butoxy)hydride is a milder reducing agent that reacts faster with acid chlorides than with aldehydes.
69
What is the mechanism of an acid chloride to an aldehyde?
70
Grignard reagents with aldehydes form what?
Secondary alcohol.
71
Grignard reagents with ketones form what?
Tertiary alcohols.
72
Grignard reagents with CO2 form what?
Reaction with carbon dioxide yields a carboxylic acid one carbon longer than Grignard reagent!
73
Grignard reagent + an ester, yields what?
Reaction 1. A ketone. Reaction 2. A teritary alcohol.
74
List the activating groups from most reactive to least reactive?
-O-. R I -N-R. - O-H. - O-R. H O I II -N-C-R -R (No lone pairs.)
75
List the activating compounds from most reactive to least reactive?
Phenoxides. Anilines. Phenols. Phenyl ethers. Anilides. Alkyl benzenes.
76
List the deactivating groups?
- NO2. (Nitro.) - SO3H. (Sulfonic acid.) - C TRIPLE BOND N. (Cyano.) Ketone or aldehyde. Ester. Quaternary ammonium.
77
Activating groups form what orientation?
Ortho or para?
78
Deactivating groups form what formation?
Meta.
79
Which deactivators form ortho or para orientation?
Halogens.
80
What is an N-Substituted Imine?
81
What is an N substituted enamine?
82
Do activators speed up or slow donw reactions?
Speed them up.
83
Is a methyl group on a benzene ring an activator or a deactivator?
An activator.
84
When reducing and acid chloride to an alcohol, what is the reducing agent?
LiAlH4.
85
What are the steps when making an alcohol from an acid chloride?
Reduce acid chloride to aldehyde. Oxidise aldehyde to alcohol.
86
What kind of alcohol does an acid chloride give?
A primary alcohol.
87
What enzyme turns ethanol into ethanal?
Alcohol dehydrogenase.
88
What is the enzyme for pyruvate to lactic acid?
Lactic acid dehydrogenase.
89
Lactic acid to pyruvic acid is what kind of reaction?
Oxidation.
90
What turns alcohol into acetaldehyde?
Alcohol dehydrogenase.
91
What turns acetaldehyde into acetic or ethanoic acid?
Aldehyde dehydrogenase.
92
What is the enzyme that converts pyruvate to lactic acid?
Lactic acid dehydrogenase.
93
What is the co enzyme that turns pyruvate to lactic acid?
NADH+ and H+.
94
What is the oxidising agent when oxidising alcohol?
NAD+.
95
What inhibits aldehyde dehydrogenase?
Disulfiram.
96
How do you turn an alkyl chloride into a nitrile?
Add CN-. E.g. NaCN.
97
How do you turn a nitrile into a ketone?
Add H30+ and the oxygen will take the place of the N-H.
98
Describe the reaction of synthesisng a nitrile from an alkyl chloride then a ketone from the nitrile?
99
When making a ketone from a nitrile, what attacks the C to N bond?
A grignard or organolithium reagent.
100
When making a nitrile from alkyl chloride, how many carbons does the chain increase by?
1.
101
What happens when you react a phenol with NaOH and HCl?
NaOH removes the H from the OH leaving O-. The O- attacks the H-Cl. Alcohol reforms.
102
A ketone or aldehyde + NH3 gives what?
The nitrogen loses 2 hydrogens and forms a double bond to the C in place of the oxygen. C=NH.
103
A ketone or aldehyde + a primary amine (NH2-CH3) gives what?
C=N-CH3.
104
A ketone or aldehyde + a hydroxyl amine (NH2-OH) gives what?
C=N-OH.
105
A ketone or aldehyde + a phenylhydrazine gives what?
106
A ketone or aldehyde + a secondary amine (R-NH-R) gives what?
107
A ketone or aldehyde + an alcohol gives what?
A hemiacetal or hemiketal.
108
A ketone or aldehyde + alcohol, what is formed?
A ketal or acteal.
109
A ketone or aldehyde + HCN and water, what is formed?
A cyanohydrin is formed. The water then adds an H to the oxygen.
110
How do you convert toluene to para chloro benzoic acid?
Tolunene + KMnO4 + NaOH + heat = Benzoic acid.
111
What are ortho para and meta directors?
112
Which donors are ortho, para or meta directing?
113
What is the Wittig reaction used for?
Making alkenes.
114
What does the Wittig reaction use?
Phosphorous.
115
What is the Wittig reaction mechanism?
116
What reagents are used for the bromination of benzene?
Br2 + FeBr3.
117
What reagents are used for the chlorination of benzene?
Cl2 + AlCl3.
118
What reagents are used for the iodination of benzene?
H+ + HNO3 + ½ I2 I+ + NO2 + H2O
119
What is the mechanism for the halogenation of benzene?
120
What is the electrophile for sulfonation?
SO3.
121
What is the electrophile for nitration?
NO2+.
122
What is the electrophile for halogenation?
FeBr3 FeCl3.
123
What is the electrophile for alkylation?
CH3-CH2-Cl.
124
What is the electrophile for acylation?
CH3-CO-Cl.
125
How can you tell if the compound is aromatic, anti aromatic or not aromatic?

Organic Chemistry (9 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2025 Bold Learning Solutions. Terms and Conditions