Exam 15: Carboxylic Acids and Nitriles

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain. -Choose best method:

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Question 1

Correct Answer:

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Amine protons interfere with the formation of Grignard reagents, so nitrile hydrolysis is the best method for carrying out this conversion.

Draw the structure of (Z)-4-methylhex-3-enoic acid.

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Question 2

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Consider the data in the table below to answer the following question(s). I -Refer to instructions. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

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Question 3

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Electron-withdrawing groups, like −CN and −OCH₃, inductively withdraw electron density, which stabilizes the resulting carboxylate anion and thus increases the acidity of the carboxylic acid. These inductive effects are strongly dependent on distance. The −CN and −OCH₃ substituents are closer to the carboxylate in the substituted acetic acids than in the substituted benzoic acids, so their effect is greater.

Which of the following does not represent a similarity between nitriles and carboxylic acids?

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Question 4

The product shown can be synthesized by two different pathways as shown by the reaction conditions. Draw the structure of starting materials that should be placed in each of the boxes.

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Question 5

An ether solution contains the following components. 2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid If this solution is extracted with a 5% solution of NaHCO₃, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO₃ layer?

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Question 6

What is the major organic product obtained from the following reaction?

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Question 7

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Give major product(s):

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Question 8

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain. -Choose best method:

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Question 9

Consider the data below to answer the following question(s). When CO₂ is bubbled through an ether solution of benzylmagnesium bromide and the resulting mixture is acidified, phenylacetic acid is produced. Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step. -What is the order of increasing reactivity for the following compounds in electrophillic aromatic substitution reactions? (least to most reactive) PK_a

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Question 10

Consider the data below to answer the following question(s). When CO₂ is bubbled through an ether solution of benzylmagnesium bromide and the resulting mixture is acidified, phenylacetic acid is produced. Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step. -Refer to instructions. This reaction can be described as a _____ process.

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Question 11

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Refer to instructions and answer the following questions. a)Give major product(s): b)Draw the structure of the intermediate product(s) that form(s).

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Question 12

Draw structures corresponding to each of the following IUPAC names. -Draw: phenylacetonitrile or phenylethanenitrile

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Question 13

Based on the following IR spectrum, this compound would be classified as:

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Question 14

At pH 3.80 calculate the % in the dissociated and undissociated form in a 0.00200 M solution of pyruvic acid, pK_a = 2.39.

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Question 15

Consider the data in the table below to answer the following question(s). I -Refer to instructions. Which of the acids in the table has the strongest conjugate base?

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Question 16

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Give major product(s):

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Question 17

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain. -Complete the following reaction sequence with the missing major organic products.

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Question 18

Draw structures corresponding to each of the following IUPAC names. -Draw: 2-propylpentanoic acid

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Question 19

Consider the data in the table below to answer the following question(s). I -Refer to instructions. Calculate the percent dissociation of 0.100 M solution of m-methoxybenzoic acid.

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Question 20

Showing 1 - 20 of 36

Exam 15: Carboxylic Acids and Nitriles

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain. -Choose best method:

Draw the structure of (Z)-4-methylhex-3-enoic acid.

Consider the data in the table below to answer the following question(s). I -Refer to instructions. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

Which of the following does not represent a similarity between nitriles and carboxylic acids?

The product shown can be synthesized by two different pathways as shown by the reaction conditions. Draw the structure of starting materials that should be placed in each of the boxes.

An ether solution contains the following components. 2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid If this solution is extracted with a 5% solution of NaHCO3, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO3 layer?

What is the major organic product obtained from the following reaction?

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Give major product(s):

Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain. -Choose best method:

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Refer to instructions and answer the following questions. a)Give major product(s): b)Draw the structure of the intermediate product(s) that form(s).

Draw structures corresponding to each of the following IUPAC names. -Draw: phenylacetonitrile or phenylethanenitrile

Based on the following IR spectrum, this compound would be classified as:

At pH 3.80 calculate the % in the dissociated and undissociated form in a 0.00200 M solution of pyruvic acid, pKa = 2.39.

Consider the data in the table below to answer the following question(s). I -Refer to instructions. Which of the acids in the table has the strongest conjugate base?

Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry. -Give major product(s):

Draw structures corresponding to each of the following IUPAC names. -Draw: 2-propylpentanoic acid

Consider the data in the table below to answer the following question(s). I -Refer to instructions. Calculate the percent dissociation of 0.100 M solution of m-methoxybenzoic acid.

Structure and Bonding

Polar Covalent Bonds; Acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Alkenes and Alkynes

Reactions of Alkenes and Alkynes

Aromatic Compounds

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Organohalides: Nucleophilic Substitutions and Eliminations

Alcohols, Phenols, and Thiols; Ethers and Sulfides

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution and Condensation Reactions

Amines and Heterocycles

Biomolecules: Amino Acids, Peptides, and Proteins

Amino Acid Metabolism

Biomolecules: Carbohydrates

Carbohydrate Metabolism

Biomolecules: Lipids and Their Metabolism

Biomolecules: Nucleic Acids and Their Metabolism

Orbitals and Organic Chemistry: Pericyclic Reactionse

Synthetic Polymerse

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An ether solution contains the following components. 2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid If this solution is extracted with a 5% solution of NaHCO₃, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO₃ layer?

At pH 3.80 calculate the % in the dissociated and undissociated form in a 0.00200 M solution of pyruvic acid, pK_a = 2.39.