Textbook Question
What is the product of the reaction of bromoethane with each of the following nucleophiles?
c. (CH3)3N
d. CH3CH2S-
7. Substitution Reactions
Nucleophilic Substitution
7:48 minutesProblem 65
Textbook Question
Draw all the products of the following reaction:
Verified step by step guidance1
Step 1: Analyze the reactants. The molecule shown is a cyclooctatrienyl cation (C8H7+), which is aromatic due to its Huckel rule compliance (4n+2 π electrons, where n=1). It is bonded to a chlorine atom. The other reactant is hydroxide ion (HO⁻), a strong nucleophile and base.
Step 2: Consider the reaction mechanism. The hydroxide ion can act as a nucleophile and attack the positively charged carbon atom bonded to chlorine, leading to a substitution reaction. This is likely an SN2 mechanism due to the steric accessibility of the carbon.
Step 3: Predict the product of the substitution. The chlorine atom will be replaced by the hydroxide group, resulting in the formation of a cyclooctatrienyl alcohol (C8H7OH).
Step 4: Consider any possible side reactions. Since hydroxide is a strong base, it could also abstract a proton from the cyclooctatrienyl cation, leading to the formation of a neutral cyclooctatriene molecule (C8H8).
Step 5: Draw all possible products. The main product is cyclooctatrienyl alcohol (C8H7OH), and a potential side product is cyclooctatriene (C8H8). Ensure to represent the aromaticity in the structures of the products.
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Video duration:
7mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanisms
Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps predict the products formed in a reaction.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups in the reactants allows chemists to anticipate how they will interact and what products will be formed. This knowledge is essential for drawing accurate reaction products.
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Stereochemistry
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions, the stereochemistry of reactants can lead to different stereoisomers as products. Understanding stereochemistry is vital for accurately representing all possible products, especially in reactions involving chiral centers.
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