/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 87 Electrophilic addition of \(\mat... [FREE SOLUTION] | 91Ó°ÊÓ

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Electrophilic addition of \(\mathrm{HCl}\) to \(\mathrm{cis}-2\) -butene gave 2-chlorobutane, which was determined not to be optically active when examined with a polarimeter. Which of the following is the better explanation for the lack of optical activity in the 2 -chlorobutane formed in this reaction? (a) 2 -Chlorobutane is not chiral. (b) Two enantiomers of 2 -chlorobutane were formed in equal amounts.

Short Answer

Expert verified
(b) Two enantiomers of 2-chlorobutane were formed in equal amounts.

Step by step solution

01

Understanding Optical Activity

Molecules are optically active if they are chiral, meaning they lack an internal plane of symmetry and have non-superimposable mirror images (enantiomers). An optically inactive sample can consist of a racemic mixture, where equal amounts of enantiomers are present, canceling each other's optical activity.
02

Molecular Structure of 2-Chlorobutane

2-Chlorobutane is a compound that can be chiral. It is made up of four different substituents attached to the second carbon, making it a chiral center. This means 2-chlorobutane can exist in two different chiral forms (enantiomers).
03

Determine if 2-Chlorobutane is Chiral

Since 2-chlorobutane has a chiral center, it is a chiral molecule. This means option (a), which suggests 2-chlorobutane isn't chiral, is not correct.
04

Racemic Mixture Formation

During electrophilic addition reactions like that of HCl to cis-2-butene, the planar nature of the carbocation intermediate allows for attack from either side, forming both enantiomers of 2-chlorobutane in equal amounts.
05

Conclusion

When both enantiomers are present in equal amounts, they form a racemic mixture, which is not optically active as the rotation of plane-polarized light by one enantiomer is canceled by the other.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Chirality
Chirality is a property of a molecule that makes it non-superimposable on its mirror image. Imagine your hands; they are mirror images but cannot be perfectly aligned regardless of how you position them. This is very similar to what happens with chiral molecules. For a molecule to be chiral, it must have a chiral center, which is typically a carbon atom bonded to four different substituents.
A chiral molecule does not have an internal plane of symmetry and can exist in two different forms, known as enantiomers.
This structural uniqueness is what allows chiral molecules to rotate plane-polarized light, a key factor in making a substance optically active.
Enantiomers
Enantiomers are pairs of molecules that are non-superimposable mirror images of each other. They play a critical role in the field of stereochemistry. These two distinct forms have identical physical and chemical properties in an achiral environment but differ in how they interact with other chiral substances.
One of the most striking features of enantiomers is their ability to rotate plane-polarized light in opposite directions. One enantiomer will rotate light in a clockwise direction, while its mirror image will rotate light counterclockwise. This is what's known as optical activity. However, if they are present in equal amounts, their effects on light cancel out, making the mixture non-optically active.
This scenario occurs in a racemic mixture, which explains why some reactions yield products that appear to be optically inactive even when chiral centers are present.
Racemic Mixture
A racemic mixture is a blend of equal amounts of two enantiomers. As a result, their abilities to rotate plane-polarized light cancel each other out, resulting in a mixture that appears optically inactive. This can easily confuse those trying to identify the chirality of the components involved.
In chemical reactions, such as the electrophilic addition of \( ext{HCl} \) to \( ext{cis-2-butene} \), racemic mixtures often form due to how molecules interact at the microscopic level.
During such reactions, intermediates form without bias to either enantiomer, leading to the creation of equal amounts of each enantiomer, making the entire mixture racemic and ultimately optically inactive.
Electrophilic Addition
Electrophilic addition is a common reaction mechanism in organic chemistry where an electrophile reacts with a molecule possessing a double bond. This reaction involves the addition of atoms to a carbon-carbon double bond and plays a significant role in forming products like 2-chlorobutane from cis-2-butene.
The reaction usually proceeds through a carbocation intermediate, which is an electron-deficient species and allows for attack from either side of the molecule. This makes it possible for two enantiomers to form.
As a result, a racemic mixture is often obtained when the product is chiral, explaining the lack of optical activity in such reactions. Understanding the mechanism helps in predicting the outcomes and characteristics of the products formed, including their optical properties.

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Most popular questions from this chapter

Write structural formulas for each of the following: (a) 3,3 -Dimethyl-2-butanone ("pinacolone") (b) 3-Hydroxybutanal ("acetaldol") (c) Ethyl pentanoate ("ethyl valerate") (d) 6-Methyl-2-heptanamine ("isooctylamine")

Fill in the blanks in the given paragraph with the most appropriate term from the following: chiral, cis, constitutional isomers, enantiomers, resonance structures, stereoisomers, trans. Isomers are different compounds that have the same molecular formula. Isomers that have their atoms connected in a different order (branched versus unbranched chain, for example) or a different sequence of bond types \((\mathrm{C}=\mathrm{CCC}\) versus \(\mathrm{CC}=\mathrm{CC},\) for example) are termed Isomers with the same order of connections and sequence of bond types, but which differ in the spatial arrangement of the atoms are called \(.\) This is often seen in compounds where substituents may be on the same or opposite sides of a carbon-carbon double bond. Substituents on the same side are described as \(\quad ;\) those on opposite sides are . A different kind of isomerism characterizes a molecule, that is, a molecule with a structure that allows for two nonsuperimposable mirror-image forms. Two nonsuperimposable mirror images are of the other

Write structural formulas for all the constitutionally isomeric \(\mathrm{C}_{4} \mathrm{H}_{9}\) alkyl groups. Check your answers with Table \(25.1,\) and note the names of these groups.

Among the many alkenes of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12}\) only one is chiral. (a) Write a structural formula for this alkene. (b) Place substituents on the tetrahedral carbons so as to represent the two enantiomers of this alkene.

Write the structural formulas of the alcohols with the formula \(\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}\) and indicate those that are chiral. Show only the \(\mathrm{C}\) atoms and the \(-\mathrm{OH}\) groups.

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