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Questions and Answers
What compound is considered a Grignard Reagent?
What compound is considered a Grignard Reagent?
- LiAlH4
- NaBH4
- RMgX (correct)
- NaH
What is produced when a hydride adds to an aldehyde in a reduction reaction?
What is produced when a hydride adds to an aldehyde in a reduction reaction?
- An alcohol (correct)
- An alkoxide (correct)
- A carboxylic acid
- A ketone
Which of the following is NOT a common reducing agent?
Which of the following is NOT a common reducing agent?
- Sodium borohydride (NaBH4)
- NADPH
- Sodium hydride (NaH) (correct)
- Lithium aluminium hydride (LiAlH4)
In biological systems, which reagent is used as a natural reducing agent in biosynthesis?
In biological systems, which reagent is used as a natural reducing agent in biosynthesis?
What are the products of the reaction between a ketone and lithium aluminium hydride followed by acid workup?
What are the products of the reaction between a ketone and lithium aluminium hydride followed by acid workup?
What is required for electrophilic substitution reactions to occur?
What is required for electrophilic substitution reactions to occur?
In the Friedel-Crafts alkylation, which species is produced from RCl and AlCl3?
In the Friedel-Crafts alkylation, which species is produced from RCl and AlCl3?
Which electrophile is generated during the nitration reaction?
Which electrophile is generated during the nitration reaction?
What type of substituents make the aromatic ring more reactive with electrophiles?
What type of substituents make the aromatic ring more reactive with electrophiles?
During Friedel-Crafts alkylation, what kind of structural changes may occur to carbocations?
During Friedel-Crafts alkylation, what kind of structural changes may occur to carbocations?
What is the role of FeBr3 in the bromination reaction?
What is the role of FeBr3 in the bromination reaction?
Which product form is typically less favored in a nitration reaction compared to ortho or para positions?
Which product form is typically less favored in a nitration reaction compared to ortho or para positions?
What is a key difference between Friedel-Crafts acylation and alkylation?
What is a key difference between Friedel-Crafts acylation and alkylation?
What is the primary outcome of nucleophilic addition of hydride to carbonyl compounds?
What is the primary outcome of nucleophilic addition of hydride to carbonyl compounds?
Which of the following is a unique feature of the carboxyl group compared to aldehydes and ketones?
Which of the following is a unique feature of the carboxyl group compared to aldehydes and ketones?
What is a characteristic of nucleophilic substitution reactions concerning carboxylic acids and their derivatives?
What is a characteristic of nucleophilic substitution reactions concerning carboxylic acids and their derivatives?
During the Friedel-Crafts acylation reaction, what role does the aluminum chloride (AlCl3) play?
During the Friedel-Crafts acylation reaction, what role does the aluminum chloride (AlCl3) play?
What is formed from the nucleophilic addition of Grignard reagents?
What is formed from the nucleophilic addition of Grignard reagents?
What happens during the nucleophilic acyl substitution mechanism?
What happens during the nucleophilic acyl substitution mechanism?
Which reagents are commonly involved in carboxylic acid synthesis through the Friedel-Crafts acylation reaction?
Which reagents are commonly involved in carboxylic acid synthesis through the Friedel-Crafts acylation reaction?
What role does the leaving group play in the nucleophilic substitution of carboxylic acid derivatives?
What role does the leaving group play in the nucleophilic substitution of carboxylic acid derivatives?
Which statement about the polarization of the carboxyl group is correct?
Which statement about the polarization of the carboxyl group is correct?
In a nucleophilic acyl substitution reaction, what is the first step?
In a nucleophilic acyl substitution reaction, what is the first step?
What is formed as a result of the nucleophilic addition of carbon-based nucleophiles to carbonyl groups?
What is formed as a result of the nucleophilic addition of carbon-based nucleophiles to carbonyl groups?
Which reaction takes place upon protonation of an alkoxide?
Which reaction takes place upon protonation of an alkoxide?
What type of product is generated from the addition of cyanide ion (CN–) to a carbonyl compound?
What type of product is generated from the addition of cyanide ion (CN–) to a carbonyl compound?
What is the role of Grignard reagents in nucleophilic addition reactions?
What is the role of Grignard reagents in nucleophilic addition reactions?
What type of alcohol is produced when ketones react with Grignard reagents?
What type of alcohol is produced when ketones react with Grignard reagents?
Which functional group is characterized by a highly polarized carbon that is an electrophile?
Which functional group is characterized by a highly polarized carbon that is an electrophile?
What type of bond formation occurs during nucleophilic addition reactions of carbonyl groups?
What type of bond formation occurs during nucleophilic addition reactions of carbonyl groups?
What is the significance of the charge stabilizing nature of orbitals in the context of acetylide anions?
What is the significance of the charge stabilizing nature of orbitals in the context of acetylide anions?
What is formed when aldehydes are treated with water under equilibrium conditions?
What is formed when aldehydes are treated with water under equilibrium conditions?
What role does acid play in nucleophilic addition reactions with alcohols?
What role does acid play in nucleophilic addition reactions with alcohols?
What type of compound is generated from the reaction of a ketone and alcohol under acidic conditions?
What type of compound is generated from the reaction of a ketone and alcohol under acidic conditions?
In the nucleophilic addition mechanism, what is the first step when a nucleophile attacks a carbonyl carbon?
In the nucleophilic addition mechanism, what is the first step when a nucleophile attacks a carbonyl carbon?
What is a hemiketal specifically derived from?
What is a hemiketal specifically derived from?
Which step in the acid-catalyzed generation of an acetal involves the formation of an oxonium ion?
Which step in the acid-catalyzed generation of an acetal involves the formation of an oxonium ion?
Which of the following is NOT a product of nucleophilic addition with water?
Which of the following is NOT a product of nucleophilic addition with water?
What happens to the product if the nucleophile contains H atoms?
What happens to the product if the nucleophile contains H atoms?
What is an acetal formed from?
What is an acetal formed from?
Which compound is generated from the reaction of an alcohol with a ketone in the presence of acid?
Which compound is generated from the reaction of an alcohol with a ketone in the presence of acid?
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Study Notes
Carboxylic Acids & Derivatives
- Important starting materials for synthesizing a wide range of compounds
- Used in the Friedel-Crafts acylation reaction
- Undergo reactions involving nucleophilic attack followed by elimination, resulting in an overall substitution reaction
Nucleophilic Substitution
- Proceeds through two steps, addition and elimination
- The overall reaction can be represented as a shorthand fashion
- Reactions are called nucleophilic addition/elimination
Polar Nature of the Carboxyl Group
- Carboxyl groups are strongly polarized, similar to aldehydes and ketones
- Nucleophiles can add to the carboxyl group
- "X" acts as a leaving group in the carboxyl group, allowing for nucleophilic substitution
- Nucleophilic substitution reactions are key for the versatility of carboxylic acids and derivatives
Aromatic Substitution Reactions
- Require a highly reactive electrophile
- Examples of aromatic substitution reactions: bromination, chlorination, iodination, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation
Friedel-Crafts Alkylation
- Alkyl halides and AlCl3 catalyst form a carbocation
- Carbocations can rearrange to more stable forms ("H-" or "R-" shifts)
- Rearrangements result in the formation of "wrong" products due to carbocation stability
Friedel-Crafts Acylation
- Acyl chlorides and AlCl3 catalyst form an acylium ion
- Acylium ions are stable and don't rearrange
- More controllable and predictable than Friedel-Crafts alkylation
Substituent Effects
- Electron donating substituents make the aromatic ring more nucleophilic and reactive with electrophiles
- Electron withdrawing substituents make the aromatic ring less nucleophilic and less reactive
Regioselectivity
- The position of the substituent on the aromatic ring can be influenced by other substituents already present on the ring
- Ortho, meta, and para positions are possible
- Ortho: adjacent to the existing substituent
- Meta: one carbon away from the existing substituent
- Para: opposite to the existing substituent
- Electron donating substituents favor ortho and para positions, while electron withdrawing groups favor meta positions
Nucleophilic Addition
- Involves the addition of a nucleophile to a carbonyl group (C=O)
- Can be carried out under acidic or basic conditions
- Results in the formation of a new carbon-carbon bond
Addition of Hydride (H-) to Carbonyl Groups
- Occurs in a two-step process
- Reduction of the carbonyl group forms an alkoxide
- Protonation of the alkoxide produces an alcohol
- Important for reducing aldehydes and ketones
Common Hydride Reducing Agents
- Lithium aluminum hydride (LiAlH4)
- Sodium borohydride (NaBH4)
- NADPH acts as nature's hydride reducing agent in biosynthesis reactions
Addition of Carbon Based Nucleophiles (Carbanions, R-) to Carbonyl Groups
- Involve carbon based nucleophiles (commonly Grignard reagents)
- Generate a new carbon-carbon bond
- Form an alkoxide in the first step and protonate the alkoxide to obtain an alcohol as product
Grignard Reagents
- Reaction with carbonyl groups forms tertiary alcohols
- Important for forming new carbon-carbon bonds in organic synthesis
- Grignard reactions are very versatile and important for organic synthesis reactions
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