Textbook Question
What are the products of the following reactions? Show all stereoisomers that are formed.
c.
d.
Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 74a
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 74aChapter 17, Problem 74a
List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols:
a. 
Verified step by step guidance1
Step 1: Analyze the structure of the tertiary alcohol provided. The alcohol group (-OH) is attached to a carbon atom that is bonded to three other groups: a phenyl group (benzene ring), an ethyl group (CH3CH2-), and a butyl group (CH3CH2CH2CH2-). This indicates that the alcohol is tertiary.
Step 2: Recall the general mechanism for forming tertiary alcohols using Grignard reagents. A Grignard reagent (R-MgX) reacts with a carbonyl compound (aldehyde or ketone) to form an alcohol. For tertiary alcohols, the carbonyl compound must be a ketone, and the Grignard reagent provides the third alkyl group.
Step 3: Identify possible combinations of ketones and Grignard reagents that could lead to the given tertiary alcohol. For example, one approach is to use acetophenone (C6H5COCH3) as the ketone and a Grignard reagent such as butyl magnesium bromide (CH3CH2CH2CH2MgBr). This reaction would add the butyl group to the carbonyl carbon, forming the desired alcohol.
Step 4: Consider alternative combinations. Another possibility is to use butanone (CH3CH2COCH3) as the ketone and phenyl magnesium bromide (C6H5MgBr) as the Grignard reagent. This reaction would add the phenyl group to the carbonyl carbon, forming the desired alcohol.
Step 5: Explore a third combination. You could use ethyl phenyl ketone (C6H5COCH2CH3) as the ketone and butyl magnesium bromide (CH3CH2CH2CH2MgBr) as the Grignard reagent. This reaction would add the butyl group to the carbonyl carbon, forming the desired alcohol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds are organic molecules characterized by the presence of a carbonyl group (C=O). They include aldehydes and ketones, which are crucial in organic synthesis. In the context of preparing tertiary alcohols, carbonyl compounds serve as electrophiles that react with nucleophiles, such as Grignard reagents, to form alcohols.
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Grignard Reagents
Grignard reagents are organomagnesium compounds represented as RMgX, where R is an organic group and X is a halogen. They act as strong nucleophiles and are used to add carbon chains to carbonyl compounds. When a Grignard reagent reacts with a carbonyl compound, it forms an alkoxide intermediate, which can be protonated to yield an alcohol.
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Tertiary Alcohols
Tertiary alcohols are alcohols where the hydroxyl (-OH) group is attached to a carbon atom that is connected to three other carbon atoms. This structure makes them more sterically hindered and less reactive than primary or secondary alcohols. In synthesis, tertiary alcohols can be formed through the reaction of carbonyl compounds with Grignard reagents, which adds a carbon chain to the carbonyl carbon.
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Related Practice
Textbook Question
List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols:
b.
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Textbook Question
What product is formed when 3-methyl-2-cyclohexenone reacts with each of the following reagents?
c. HBr
d. CH3CH2SH
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Textbook Question
What product is formed when 3-methyl-2-cyclohexenone reacts with each of the following reagents?
a. CH3MgBr followed by H3O+
b. (CH3CH2)2CuLi followed by H3O+
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Textbook Question
How could you convert N-methylbenzamide to the following compounds?
d. benzyl alcohol
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Textbook Question
How could you convert N-methylbenzamide to the following compounds?
c. methyl benzoate
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