Chapter 10: Structure and Synthesis of Alcohols Flashcards
(197 cards)
1
Q
What are alcohols?
A
Organic compounds containing hydroxy (-OH) groups
Alcohols are versatile synthetic intermediates in organic chemistry.
2
Q
What is the IUPAC suffix used for alcohols?
A
-ol
3
Q
What are the two main components of peppermint oil?
A
- l-menthol
- l-menthone
4
Q
What is the definition of primary alcohol?
A
An alcohol with the -OH group attached to a primary carbon atom
5
Q
What is a secondary alcohol?
A
An alcohol with the -OH group attached to a secondary carbon atom
6
Q
What is a tertiary alcohol?
A
An alcohol with the -OH group attached to a tertiary carbon atom
7
Q
What are phenols?
A
Compounds with a hydroxy group bonded directly to an aromatic ring
8
Q
What is the bond angle in methanol?
A
108.9°
9
Q
What is the bond angle in water?
A
104.5°
10
Q
How do you name an alcohol using IUPAC nomenclature?
A
- Name the longest carbon chain with the -OH group
- Drop the final -e and add -ol
- Number the chain to give the lowest number to the -OH group
11
Q
What is the common name for methyl alcohol?
A
Methanol
12
Q
What is the IUPAC name for 2-methylpropan-1-ol?
A
Isobutyl alcohol
13
Q
What are diols?
A
Alcohols with two -OH groups
14
Q
What is a glycol?
A
A 1,2-diol with two hydroxy groups on adjacent carbon atoms
15
Q
How are glycols typically synthesized?
A
By the hydroxylation of alkenes
16
Q
What is the IUPAC name for ethylene glycol?
A
Ethane-1,2-diol
17
Q
What property do alcohols and phenols share?
A
Both contain a hydroxy (-OH) group
18
Q
What is the structure of ethyl alcohol?
A
CH3-CH2-OH
19
Q
True or False: The hydroxy group takes precedence over double and triple bonds in nomenclature.
A
True
20
Q
What is the IUPAC name for butan-2-ol?
A
A secondary alcohol
21
Q
What is the common name for 1-bromo-3,3-dimethylbutan-2-ol?
A
A complex alcohol that requires IUPAC nomenclature
22
Q
What is the bond length of the C-O bond in methanol?
A
1.4 A
23
Q
What are some common uses of isopropyl alcohol?
A
As a skin cleanser for injections and minor cuts
24
Q
Fill in the blank: Alcohols can be converted to most other _______ groups.
A
functional
25
What is the order of precedence of functional groups in naming organic compounds?
* Carboxylic acids
* Esters
* Aldehydes
* Ketones
* Alcohols
* Amines
* Alkenes, alkynes
* Alkanes
26
What happens to the -OH functional group when it appears on a structure with a higher-priority functional group?
It is named as a hydroxy substituent
27
What is the IUPAC name for ethylene glycol?
ethane-1,2-diol
## Footnote
Ethylene glycol is commonly used as automotive antifreeze.
28
What is the common name for propane-1,2-diol?
propylene glycol
## Footnote
Propylene glycol is used in medicines and foods.
29
What does the term 'ortho' refer to in phenols?
1,2-disubstituted
## Footnote
The terms ortho, meta, and para are used to describe the positions of substituents on the benzene ring.
30
What is the common name for 2-bromophenol?
ortho-bromophenol
31
What is the IUPAC name for catechol?
benzene-1,2-diol
32
What is the application of concentrated phenol?
It is a potent neurotoxin and causes deep, painless burns.
33
Which alcohol is also known as methyl alcohol?
methanol
34
What is the boiling point of ethanol?
78 °C
35
Which intermolecular forces are primarily responsible for ethanol's high boiling point?
Hydrogen bonding and dipole-dipole attractions
36
Fill in the blank: The alcohol with the formula CH3CH2OH is commonly known as _______.
ethyl alcohol
37
What is the density of propan-2-ol?
0.79 g/ml
38
True or False: Dimethyl ether can engage in hydrogen bonding.
False
## Footnote
Dimethyl ether lacks -O-H hydrogens necessary for hydrogen bonding.
39
What effect does the size of the alkyl group have on the solubility of alcohols in water?
Solubility decreases as the alkyl group becomes larger.
40
What is the common name for 2-methylphenol?
ortho-cresol
41
What is the solubility of methyl alcohol in water at 25 °C?
miscible
42
What happens to the water solubility of alcohols with larger alkyl groups?
It decreases.
43
What is the boiling point of glycerol?
290 °C
44
True or False: Methanol is less flammable than gasoline.
True
45
What is the IUPAC name for isopropyl alcohol?
propan-2-ol
46
What is the primary use of methanol in industry?
It is used as a common industrial solvent.
47
What is the density of ethanol?
0.79 g/ml
48
Fill in the blank: The molecular formula for ethane-1,2-diol is _______.
HOCH2CH2OH
49
What is the boiling point of butan-2-ol?
100 °C
50
What is the common name for phenylmethanol?
benzyl alcohol
51
Which alcohol is produced from the destructive distillation of wood chips?
methanol
52
What is the boiling point of propan-1-ol?
97 °C
53
What type of alcohol is commonly used in cosmetics and pharmaceuticals?
propylene glycol
54
What is methanol used for?
Methanol is a starting material for a variety of methyl ethers, methyl esters, and other compounds used in plastics, medicines, fuels, and solvents.
55
Why was methanol used in the Indianapolis 500 from 1965-2006?
Methanol was used because it is less flammable than gasoline and water is effective against methanol fires.
56
What are the advantages of using methanol as a fuel?
Advantages include high octane rating, low pollutant emissions, and lower flammability.
57
What is a disadvantage of using methanol as a fuel?
Methanol has lower energy content, requiring 1.7 g to produce the same energy as 1 g of gasoline.
58
How does methanol affect fuel-system components?
Methanol is hard on rings, seals, and plastic fuel-system parts due to its excellent solvent properties.
59
What historical significance does ethanol have?
Ethanol was likely discovered when rotten fruit was consumed, leading to the fermentation of fruit juices.
60
What is E85?
E85 is a fuel blend containing 85% ethanol and 15% gasoline.
61
What impact do government subsidies have on ethanol production?
Government subsidies have increased the price of food grains while having little impact on fuel supplies.
62
What is the typical alcohol concentration in the alcoholic solution resulting from fermentation?
The alcoholic solution typically contains only 12-15% alcohol.
63
What process is used to increase ethanol concentration for hard liquors?
Distillation is used to increase the ethanol concentration to about 40-50%.
64
What is a minimum-boiling azeotrope?
A minimum-boiling azeotrope is a mixture of liquids that boils at a lower temperature than either of its components.
65
How can absolute alcohol be obtained from 95% ethanol?
By passing the 95% azeotrope through a dehydrating agent such as anhydrous calcium oxide (CaO).
66
What is the primary method for synthesizing industrial ethanol since World War II?
The gas-phase reaction of water with ethylene using catalysts at high-temperature and high-pressure.
67
True or False: Methanol is less toxic than ethanol.
False.
68
What is denatured alcohol?
Denatured alcohol is ethanol that contains impurities making it undrinkable.
69
What is the typical composition of rubbing alcohol?
Rubbing alcohol usually contains about 70% isopropyl alcohol and 30% water.
70
What is the effect of the hydroxy proton in alcohols?
The hydroxy proton of an alcohol is weakly acidic.
71
What happens to alkoxide ions in the presence of a strong base?
A strong base can remove the hydroxy proton to give an alkoxide ion.
72
Which alcohol is more acidic: methanol or tert-butyl alcohol?
Methanol.
73
What is the relationship between acidity and alkyl group substitution in alcohols?
Acidity decreases as substitution on the alkyl group increases.
74
What enhances the acidity of alcohols?
Substitution by electron-withdrawing halogen atoms enhances the acidity.
75
How do alkoxide ions behave in chemical reactions?
Alkoxide ions are strong nucleophiles and strong bases.
76
What is the effect of phenol compared to cyclohexanol in terms of acidity?
Phenol is nearly 100 million times more acidic than cyclohexanol.
77
What historical figure used phenol as an antiseptic?
British surgeon Joseph Lister.
78
What factor contributes to the stability of the phenoxide ion?
The negative charge is delocalized over the oxygen and three carbon atoms of the ring.
79
What stabilizes the negative charge in a resonance hybrid involving oxygen?
The ability to spread the negative charge over four atoms rather than concentrating it on just one atom
## Footnote
This produces a more stable ion.
80
What is the pKa of phenol?
10.0
81
What happens when phenol reacts with sodium hydroxide?
Phenoxide anions are produced
## Footnote
The reaction is exothermic and favors the formation of sodium phenoxide.
82
What was phenol historically called due to its ability to neutralize common bases?
Carbolic acid
83
How is a nitro group (-NO2) related to charge stabilization?
It stabilizes a negative charge on an adjacent carbon atom through resonance.
84
What is the application of phenol in biochemistry?
It is used to separate cellular DNA from proteins.
85
What occurs when an aqueous phenol solution is used to isolate DNA?
DNA dissolves while proteins precipitate.
86
Name two nitrophenols that are much more acidic than phenol.
2-nitrophenol, 3-nitrophenol
87
Fill in the blank: Alcohols are important synthetic intermediates because they can be synthesized directly from a wide variety of other _______.
functional groups
88
What are the methods for synthesizing alcohols from alkenes?
1. Acid-catalyzed hydration
2. Oxymercuration-demercuration
3. Hydroboration-oxidation
4. Dihydroxylation
89
What is the common mechanism for nucleophilic substitution on an alkyl halide?
Usually via the SN2 mechanism
90
What do organometallic compounds contain?
Covalent bonds between carbon atoms and metal atoms
91
What is the significance of Grignard reagents in organic synthesis?
They are used to form carbon-carbon bonds.
92
Which type of compounds can Grignard reagents be made from?
Primary, secondary, and tertiary alkyl halides, as well as vinyl and aryl halides.
93
True or False: Alkyl fluorides generally react with Grignard reagents.
False
94
What is the reactivity order of halides in forming Grignard reagents?
R-I > R-Br > R-Cl >> R-F
95
What type of solvents are suitable for Grignard reactions?
Dry ethers such as diethyl ether
## Footnote
Other solvents may also be used, but they should not contain acidic protons.
96
What do Grignard and organolithium reagents act as when reacting with carbonyl groups?
Strong nucleophiles and strong bases
97
What is the first product formed when a Grignard reagent attacks a carbonyl compound?
An alkoxide ion
98
What type of alcohol is produced from the addition of a Grignard reagent to formaldehyde?
Primary alcohol
99
Fill in the blank: The formation of the Grignard reagent involves the reaction of an alkyl halide with _______ in an anhydrous ether solution.
Magnesium
100
What is the result of adding a Grignard reagent to a ketone?
An alkoxide salt, which can be protonated to form an alcohol.
101
What type of alcohol is formed when Grignard reagents add to formaldehyde?
Primary alcohol
## Footnote
Example: pentan-1-ol can be synthesized by adding a Grignard reagent to formaldehyde.
102
What are the products of Grignard reagent addition to aldehydes?
Secondary alcohols
## Footnote
The two alkyl groups of the secondary alcohol are from the Grignard reagent and the aldehyde.
103
How are tertiary alcohols formed using Grignard reagents?
By adding Grignard reagents to ketones
## Footnote
Tertiary alcohols have three alkyl groups bonded to the carbinol carbon.
104
What is the general reaction of Grignard reagents with acid chlorides?
They react to form tertiary alcohols after protonation
## Footnote
The reaction involves two equivalents of Grignard reagents.
105
What is the structure of an acid chloride?
R-C-Cl
## Footnote
In acid chlorides, the hydroxy group of the acid is replaced by a chlorine atom.
106
What are the steps involved in converting an acid chloride to a tertiary alcohol?
* Add Grignard reagent to form an unstable intermediate
* Expel a chloride ion to yield a ketone
* Add a second equivalent of Grignard reagent
* Protonate to form the tertiary alcohol
107
True or False: Grignard reagents can react with ethers.
False
## Footnote
Ethers are generally unreactive to Grignard reagents, but epoxides are exceptions due to ring strain.
108
What is the product when a Grignard reagent reacts with ethylene oxide?
Primary alcohols with two additional carbon atoms
## Footnote
The nucleophilic attack opens the epoxide ring.
109
What defines the carbinol carbon in alcohol synthesis?
The carbon atom with the OH group attached
## Footnote
The groups on this carbon determine the type of alcohol produced.
110
Fill in the blank: A secondary alcohol can be synthesized by adding a Grignard reagent to _______.
Aldehyde
111
What happens to the alkoxide ion during the reaction of acid chlorides with Grignard reagents?
It acts as a leaving group
## Footnote
This helps stabilize a negatively charged intermediate.
112
What is the result of adding two equivalents of Grignard reagents to a formate ester?
Secondary alcohols with two identical alkyl groups
## Footnote
Example: Ethyl formate reacts to form secondary alcohols.
113
What is the mechanism of Grignard reaction with esters?
* First equivalent forms an unstable intermediate
* Expels an alkoxide ion to yield a ketone
* Second equivalent reacts with the ketone to form a tertiary alcohol
114
What type of alcohol is formed when Grignard reagents add to ketones?
Tertiary alcohols
115
Fill in the blank: Grignard reagents added to _______ produce primary alcohols.
Formaldehyde
116
What is the significance of the carbinol carbon in alcohol synthesis?
It determines the type of alcohol produced based on the groups attached.
117
What type of alcohol is synthesized when a Grignard reagent reacts with a ketone?
Tertiary alcohol
## Footnote
Tertiary alcohols have three alkyl groups on the carbinol carbon.
118
True or False: The reaction of Grignard reagents with epoxides results in the new OH group being on the same carbon as the new bond.
False
## Footnote
The new OH group appears on the second carbon from where the Grignard formed a new bond.
119
What happens when an excess of ethylmagnesium bromide is added to methyl benzoate?
It forms 3-phenylpentan-3-ol
## Footnote
This is a result of two equivalents of Grignard reagents reacting with the ester.
120
What type of alcohol can be synthesized from a Grignard reagent reacting with a ketone?
Tertiary alcohol
121
What are Grignard reagents?
Organometallic compounds that are strong bases and nucleophiles
## Footnote
They are formed from alkyl halides and magnesium in dry ether.
122
What is the reaction of Grignard reagents with alkyl halides?
They do not easily displace halides, preventing undesired coupling products
## Footnote
This selectivity allows for the formation of Grignard reagents without side reactions.
123
What are lithium dialkylcuprates also known as?
Gilman reagents
## Footnote
They are used for coupling reactions with alkyl halides.
124
What is the general reaction for coupling with lithium dialkylcuprates?
R2CuLi + R'-X -> R-R' + R-Cu + LiX
## Footnote
This reaction can couple two carbon chains efficiently.
125
How are lithium dialkylcuprates formed?
By the reaction of two equivalents of organolithium reagents with cuprous iodide
## Footnote
2 R-Li + CuI -> R2CuLi + LiI.
126
What is a significant characteristic of the reaction of lithium dialkylcuprates with vinyl halides?
They preserve the stereochemistry of the vinyl halide
## Footnote
This indicates that the mechanism does not involve SN2 reactions.
127
What is the reactivity of lithium dialkylcuprates towards carbonyl groups compared to Grignard reagents?
Less reactive towards carbonyl groups than Grignard reagents
## Footnote
They react slower with ketones than with acid chlorides.
128
What is the primary use of Grignard and organolithium reagents?
To react with carbonyl compounds to form alcohols
## Footnote
They add alkyl groups to carbonyl compounds.
129
What happens when Grignard reagents react with water?
They react vigorously and irreversibly, destroying the reagent
## Footnote
This necessitates the use of dry conditions.
130
What is the outcome of adding ethyllithium to water?
It produces ethane and destroys the reagent
## Footnote
Ethane bubbles to the surface due to its low acidity.
131
What types of groups are incompatible with Grignard and organolithium reagents?
O-H, N-H, S-H, and terminal alkyne groups
## Footnote
These groups can protonate the reagents.
132
What do sodium borohydride and lithium aluminum hydride reduce?
They reduce carbonyl compounds to alcohols
## Footnote
This involves adding hydrogen atoms across the C=O bond.
133
What is the difference between sodium borohydride and lithium aluminum hydride in terms of reactivity?
Lithium aluminum hydride is a stronger reducing agent
## Footnote
LAH can reduce less reactive carbonyl groups like acids and esters.
134
What is the mechanism of reduction for carbonyl groups using hydride reagents?
Hydride ion transfers to carbon, forming an alkoxide ion
## Footnote
Then, protonation of the alkoxide gives the alcohol.
135
What is a key feature of the reaction conditions for lithium aluminum hydride?
LAH and water are incompatible; water is added in a separate step
## Footnote
This prevents explosions and fires.
136
What type of alcohol does sodium borohydride produce from aldehydes?
Primary alcohols
## Footnote
It reduces ketones to secondary alcohols.
137
What is the result of using lithium aluminum hydride on carboxylic acids?
Reduces them to primary alcohols
## Footnote
LAH is effective on various carbonyl derivatives.
138
What is LAH and its primary function?
LAH (Lithium aluminum hydride) is a strong reagent that reduces ketones to secondary alcohols and aldehydes, acids, and esters to primary alcohols.
139
What is the primary use of sodium borohydride (NaBH4)?
NaBH4 is usually the best reagent for the reduction of a simple ketone or aldehyde.
140
What happens during the reduction of ketones and aldehydes using LAH?
LAH reduces ketones to secondary alcohols and aldehydes, acids, and esters to primary alcohols.
141
Fill in the blank: The reduction of an aldehyde or ketone produces a _______ or _______ alcohol.
primary or secondary
142
What is a key aspect of the reaction mechanism when using LAH?
The lithium salt of the alkoxide ion is formed first, followed by protonation with dilute acid.
143
True or False: Sodium borohydride can reduce acids and esters in the presence of a ketone or aldehyde.
False
144
What type of alcohol is produced when reducing an ester or carboxylate anion with LAH?
A primary alcohol.
145
What is the difference between oxidation and reduction in organic chemistry?
Reduction is the formation of a new C-H bond and a decrease in C-O bonds; oxidation is the opposite.
146
What are the two reducing agents mentioned for reducing carbonyl compounds?
* NaBH4
* LiAlH4
147
What is the role of Raney nickel in the hydrogenation process?
Raney nickel acts as a catalyst for the hydrogenation of ketones and aldehydes to alcohols.
148
What is the IUPAC naming convention for thiols?
IUPAC names for thiols are derived from alkane names using the suffix -thiol.
149
Fill in the blank: Thiols can be prepared by _______ reactions of sodium hydrosulfide with unhindered alkyl halides.
SN2
150
What is the significance of thiols in heavy metal poisoning treatment?
Thiols can complex with heavy metals, making them useful as antidotes, such as dimercaprol for arsenic poisoning.
151
True or False: Thiols are less acidic than alcohols.
False
152
What happens to thiols under oxidation conditions?
Thiols are oxidized to form disulfides.
153
What is the common name for methanethiol?
Methyl mercaptan.
154
What is the effect of introducing disulfide bonds in proteins?
It helps proteins withstand higher temperatures and maintain active conformation.
155
What is a common oxidant that can convert thiols to sulfonic acids?
KMnO4, nitric acid (HNO3), or bleach (NaOCl).
156
What is the structure of a disulfide bond?
R-S-S-R, formed from two thiol molecules.
157
What is the relationship between thiols and the characteristic odor of skunks?
Skunks spray thiols to protect themselves, which gives them their strong odor.
158
What is the pKa value of ethanethiol and ethanethiolate?
* Ethanethiol: 15.7
* Ethanethiolate: 10.5
159
What is the primary alcohol produced from the reduction of benzaldehyde?
Benzyl alcohol.
160
What do enzymes contain to remove protein and blood stains?
Enzymes contain the ability to remove protein and blood stains by replacing strategically located amino acid residues with cysteines
## Footnote
Modified enzymes maintain their active conformation in hot water.
161
What is the structure of a disulfide bridge?
A disulfide bridge involves two cysteine residues linked by a sulfur-sulfur bond.
## Footnote
This structure is represented as R-S-S-R.
162
What happens during vigorous oxidation of thiols?
Vigorous oxidation converts thiols to sulfonic acids.
## Footnote
Oxidants such as KMnO4, nitric acid (HNO3), or bleach (NaOCl) can facilitate this reaction.
163
How many electrons can sulfur have in an expanded octet?
Sulfur can have 10 or 12 electrons in an expanded octet, as seen in SF4 (10 electrons) and SF6 (12 electrons).
164
What is the general formula for a thiol?
The general formula for a thiol is R-S-H.
165
What is glutathione and its function?
Glutathione is a tripeptide containing a thiol group that serves as a mild reducing agent to detoxify peroxides and maintain cysteine residues in hemoglobin.
## Footnote
It can also detoxify alkylating agents.
166
What are acid derivatives?
Acid derivatives are compounds related to carboxylic acids with other electron-withdrawing groups instead of the -OH group.
## Footnote
Examples include acid chlorides, esters, and amides.
167
How are alcohols classified?
Alcohols are classified as primary, secondary, or tertiary based on the carbon atom to which the hydroxy group is attached.
## Footnote
This classification depends on whether the carbon is primary, secondary, or tertiary.
168
What is a sulfonic acid?
A sulfonic acid is a strongly acidic compound with the formula R-SO3H, formed by the vigorous oxidation of a thiol.
## Footnote
It is characterized by the presence of a sulfonic group.
169
What is the role of Grignard reagents in alcohol synthesis?
Grignard reagents are used to synthesize primary, secondary, and tertiary alcohols by reacting with carbonyl compounds.
## Footnote
They are organometallic reagents of the form R-MgX.
170
What defines a primary alcohol?
A primary alcohol is defined as having the hydroxy group attached to a primary carbon atom.
171
What is the structure of a ketone?
A ketone has the structure R-C(=O)-R', where R and R' are alkyl or aryl groups.
172
What is a diol?
A diol is a compound with two alcohol -OH groups.
## Footnote
The term glycol is commonly used for 1,2-diols.
173
What is a mercaptan?
A mercaptan is the sulfur analogue of an alcohol, represented as R-SH.
174
What is the significance of lithium dialkylcuprate in organic chemistry?
Lithium dialkylcuprate is used to couple with alkyl halides in organic synthesis.
## Footnote
It is also known as a Gilman reagent.
175
What does the term 'hydrophilic' mean?
Hydrophilic means being attracted to water and water-soluble.
176
What does the term 'hydrophobic' mean?
Hydrophobic means being repelled by water and water-insoluble.
177
What is the general reaction for reducing carbonyl groups using hydride reagents?
The general reaction involves hydride reagents reducing carbonyl groups to form alcohols.
178
What are essential problem-solving skills in organic chemistry?
Essential skills include drawing structures, predicting boiling points, converting compounds to alcohols, and proposing syntheses.
## Footnote
Specific problems illustrate these skills.
179
What is the difference between an aldehyde and a ketone?
An aldehyde has one hydrogen and one alkyl group on the carbonyl carbon, while a ketone has two alkyl groups.
## Footnote
Example: Formaldehyde (H2C=O) is an aldehyde.
180
What is the structure of l-phenylbutan-1-ol?
A primary alcohol with a phenyl group attached to the first carbon of a butanol chain
## Footnote
Primary alcohols have the hydroxyl (-OH) group attached to a carbon atom that is attached to only one other carbon atom.
181
What is the product of the synthesis of l-phenylbut-1-ene?
An alkene formed from the dehydration of l-phenylbutan-1-ol
## Footnote
Alkenes are characterized by at least one carbon-carbon double bond.
182
What is the synthesis pathway for l-phenylbutan-2-ol?
Reduction of l-phenylbutan-2-one or Grignard addition to a ketone
## Footnote
Grignard reagents are used to form alcohols by adding to carbonyls.
183
How can you synthesize 2-phenylpentan-2-ol?
By reducing 2-phenylpentan-2-one or via Grignard reaction with appropriate starting materials
## Footnote
2-phenylpentan-2-ol is a secondary alcohol.
184
What is the role of Grignard reagents in synthesizing alcohols?
They react with carbonyl compounds to form alcohols
## Footnote
Grignard reagents are organomagnesium compounds that act as nucleophiles.
185
Fill in the blank: 1-cyclohexylethanol can be prepared from _______.
[acetaldehyde, CH3CHO]
## Footnote
This involves the reaction of a Grignard reagent with acetaldehyde.
186
True or False: Vinyl alcohols are stable compounds.
False
## Footnote
Vinyl alcohols rapidly isomerize to carbonyl compounds.
187
What is the mechanism for the acid-catalyzed loss of water from propane-2,2-diol?
Protonation of the hydroxyl group followed by elimination of water to form acetone
## Footnote
This process involves carbocation rearrangement.
188
Explain the isomerization mechanism of vinyl alcohol to acetaldehyde.
Protonation of the alcohol followed by rearrangement to form the carbonyl
## Footnote
The reaction is favored due to the stability of the carbonyl compound.
189
What happens when compound A (C7H11Br) reacts with magnesium in ether?
It forms the Grignard reagent B (C7H11MgBr)
## Footnote
This is a standard method for preparing Grignard reagents.
190
What is the expected product when Grignard reagent B reacts with acetone?
D (C10H18O), a tertiary alcohol
## Footnote
The reaction involves nucleophilic attack on the carbonyl carbon of acetone.
191
What is the effect of using dilute hydrogen peroxide in removing skunk oil?
Oxidizes thiols to sulfonic acids, neutralizing the odor
## Footnote
Skunk oil primarily contains 3-methylbutane-1-thiol and but-2-ene-1-thiol.
192
How can 1-methylcyclohexanol be synthesized?
From methylenecyclohexane using hydrogenation and other reagents
## Footnote
Hydrogenation typically involves the addition of H2 across double bonds.
193
Compare the properties of propan-2-ol and its hexafluoro analog.
Propan-2-ol has a boiling point of 82 °C, while the hexafluoro analog has a boiling point of 58 °C
## Footnote
Differences in molecular weight and dipole moments influence boiling points.
194
Why is the hexafluoro analog a stronger acid than propan-2-ol?
Due to the electron-withdrawing effect of fluorine atoms
## Footnote
Electron-withdrawing groups stabilize the conjugate base.
195
What reagent can be used to introduce deuterium into organic compounds?
LiAlD4
## Footnote
LiAlD4 is a reducing agent equivalent to LiAlH4 but provides deuterium instead of hydrogen.
196
How can 2-phenylethanol be synthesized from formaldehyde?
By adding formaldehyde to a suitable Grignard reagent
## Footnote
Formaldehyde acts as the electrophile in this reaction.
197
What is the result of ozonolysis reactions using pyridine as a solvent?
Generates aldehydes and ketones without isolating intermediates
## Footnote
This method allows for more efficient synthesis of carbonyl compounds.
