Predict the product of the following reaction sequences. (a)
Verified step by step guidance
1
Identify the starting material as a brominated alkane with a phenyl group attached, specifically (R)-1-phenylethyl bromide.
In the first step, sodium cyanide (NaCN) in tetrahydrofuran (THF) is used. This is a nucleophilic substitution reaction where the cyanide ion (CN-) will replace the bromine atom, forming a nitrile group. The product will be (R)-1-phenylethyl cyanide.
In the second step, lithium aluminum hydride (LiAlH4) in THF is used. LiAlH4 is a strong reducing agent that will reduce the nitrile group to a primary amine. The product will be (R)-1-phenylethylamine.
In the third step, the reaction mixture is quenched with H3O+. This step is typically used to neutralize any remaining reactive species and to protonate the amine, if necessary, to ensure the final product is in its neutral form.
The final product of the reaction sequence is (R)-1-phenylethylamine, which retains the stereochemistry of the starting material due to the nature of the reactions involved.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above
Video duration:
2m
Play a video:
Was this helpful?
Key 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 outcome of reactions and the stability of products formed.
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of reactions that can occur. For example, alcohols, carboxylic acids, and amines each have distinct behaviors in chemical reactions.
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for predicting the products of reactions, especially in cases where chirality or geometric isomerism plays a role. Understanding stereochemistry helps in determining the specific isomers that may be produced in a reaction.