Textbook Question
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.
i. (Z)-2,3-dichloro-2-butene + H2, Pd/C
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Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
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. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 87k,l
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 87k,lChapter 7, Problem 87k,l
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.
k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C
l. (E)-3,4-dimethyl-3-hexene + H2, Pd/C
Verified step by step guidance1
Step 1: Understand the reaction type. The reaction involves the addition of hydrogen (H₂) to an alkene in the presence of a catalyst (Pd/C). This is a catalytic hydrogenation reaction, which converts alkenes into alkanes by breaking the π-bond and adding hydrogen atoms to the carbons involved in the double bond.
Step 2: Analyze the starting materials. For (Z)-3,4-dimethyl-3-hexene, the double bond is in the Z-configuration, meaning the higher-priority groups on each carbon of the double bond are on the same side. For (E)-3,4-dimethyl-3-hexene, the higher-priority groups are on opposite sides of the double bond.
Step 3: Predict the product of hydrogenation. In catalytic hydrogenation, the double bond is completely reduced to a single bond, and two hydrogen atoms are added to the carbons that were part of the double bond. The resulting product will be a saturated alkane. Since the reaction occurs on a flat metal surface, the addition of hydrogen is syn (on the same side).
Step 4: Consider stereoisomerism. In this case, the product of hydrogenation will not have stereoisomers because the resulting alkane does not contain any stereogenic centers. The double bond is fully reduced, and the molecule becomes a simple alkane with no chiral centers.
Step 5: Draw the products. For both (Z)-3,4-dimethyl-3-hexene and (E)-3,4-dimethyl-3-hexene, the product will be the same: 3,4-dimethylhexane. The stereochemistry of the starting material does not affect the final product in this reaction because the double bond is completely reduced.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrogenation
Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to an unsaturated compound, typically an alkene or alkyne, in the presence of a catalyst such as palladium on carbon (Pd/C). This process converts double or triple bonds into single bonds, resulting in saturated hydrocarbons. Understanding hydrogenation is crucial for predicting the products of the given reactions.
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00:48
The definition of hydrogenation.
Stereoisomerism
Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. In the context of alkenes, stereoisomers can arise from the presence of double bonds, leading to cis/trans or E/Z configurations. Recognizing the potential for stereoisomers is essential when determining the products of the reactions involving (Z)- and (E)-alkenes.
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01:58Determining when molecules are stereoisomers.
Alkene Reactivity
Alkenes are reactive due to the presence of a carbon-carbon double bond, which can undergo various reactions, including addition reactions. The reactivity of alkenes is influenced by their substitution pattern, which affects the stability of the intermediates formed during reactions. Understanding the reactivity of alkenes helps in predicting the outcome of the hydrogenation reactions presented in the question.
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Related Practice
Textbook Question
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.
h. cis-2-butene + HBr
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Textbook Question
The reaction of an alkene with diazomethane forms a cyclopropane ring. Propose a mechanism for the reaction. (Hint: It is a concerted reaction.)
1398
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Textbook Question
A, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2 over Pd/C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration/oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C6H10O2. Provide structures for A–F.
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Textbook Question
Of the possible products shown for the following reaction, are there any that will not be formed?
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Textbook Question
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.
j. (E)-2,3-dichloro-2-butene + H2, Pd/C
1324
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