Which of the noncyclic isomers of bromochloropropene are optically active?

Short Answer

Expert verified
The noncyclic isomers of bromochloropropene that are optically active are 1-Bromo-2-chloropropene, 2-Bromo-1-chloropropene, and 3-Bromo-2-chloropropene, as they each have at least one chiral center.

Step by step solution

01

Identify all possible noncyclic isomers of bromochloropropene

Let's find all the possible noncyclic isomers for bromochloropropene (C3H3BrCl). Bromochloropropene has three carbon atoms, one bromine atom, and one chlorine atom. The isomers can have different placements of the bromine and chlorine atoms in the carbon chain. There are four possible isomers: 1. 1-Bromo-1-chloropropene: Br and Cl are both attached to the first carbon atom. 2. 1-Bromo-2-chloropropene: Br is attached to the first carbon atom, and Cl is attached to the second carbon atom. 3. 2-Bromo-1-chloropropene: Br is attached to the second carbon atom, and Cl is attached to the first carbon atom. 4. 3-Bromo-2-chloropropene: Br is attached to the third carbon atom, and Cl is attached to the second carbon atom.
02

Understand the concept of optical activity

Optical activity is the ability of a molecule to rotate plane-polarized light. A molecule is optically active if it has at least one chiral center. A chiral center is an atom that has four different groups attached to it and is non-superimposable on its mirror image. In the case of the isomers of bromochloropropene, we need to identify which isomers have chiral centers.
03

Identify isomers with chiral centers

Now, let's examine each isomer to see if it has a chiral center: 1. 1-Bromo-1-chloropropene: The first carbon atom has two different groups (Br and Cl) attached, but it also has two identical hydrogen atoms. Hence, it is not a chiral center. 2. 1-Bromo-2-chloropropene: The second carbon atom has four different groups (Br, Cl, H, and a methyl group) attached to it. This makes it a chiral center. 3. 2-Bromo-1-chloropropene: The first carbon atom has four different groups (Br, Cl, H, and a methyl group) attached to it. This makes it a chiral center. 4. 3-Bromo-2-chloropropene: The second carbon atom has four different groups (Br, Cl, H, and a methyl group) attached to it. This makes it a chiral center.
04

Determine the optically active isomers

Since 1-Bromo-2-chloropropene, 2-Bromo-1-chloropropene, and 3-Bromo-2-chloropropene have at least one chiral center, they are optically active. In conclusion, the noncyclic isomers of bromochloropropene that are optically active are 1-Bromo-2-chloropropene, 2-Bromo-1-chloropropene, and 3-Bromo-2-chloropropene.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d},\) see Exer cise 62 a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(C_{4} H_{8}\) is reacted with \(H_{2} O\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with HCl, 1 -chloro- 1 -methylcyclo hexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?

Poly(lauryl methacrylate) is used as an additive in motor oils to counter the loss of viscosity at high temperature. The structure is The long hydrocarbon chain of poly(lauryl methacrylate) makes the polymer soluble in oil (a mixture of hydrocarbons with mostly 12 or more carbon atoms). At low temperatures the polymer is coiled into balls. At higher temperatures the balls uncoil and the polymer exists as long chains. Explain how this helps control the viscosity of oil.

What types of interactions can occur between the side chains of the following amino acids that would help maintain the tertiary structure of a protein? a. cysteine and cysteine b. glutamine and serine c. glutamic acid and lysine d. proline and leucine

Why is it preferable to produce chloroethane by the reaction of HCI(g) with ethene than by the reaction of \(\mathrm{Cl}_{2}(g)\) with ethane? (See Exercise 62.)

For the following formulas, what types of isomerism could be exhibited? For each formula, give an example that illustrates the specific type of isomerism. The types of isomerism are structural, geometric, and optical. a. \(C_{6} H_{12}\) b. \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O} \quad\) c. \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Br}_{2}\)

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free