Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 5: Q-5-25P (page 280)

The following structures are optically active compounds. Star (*) the asymmetric carbon atoms in these structures.

Short Answer

Expert verified

When four different atoms or groups are attached to the central carbon atom, it is known as asymmetric carbon. The chirality of a structure can be predicted by the presence of an asymmetric center. Though an asymmetric carbon atom is a very important aspect in determining the chirality of a molecule, it is not the only factor determining chirality. Several ring structures also show axial chirality.

Step by step solution

01

Asymmetric carbon

When four different atoms or groups are attached to the central carbon atom, it is known as asymmetric carbon. The chirality of a structure can be predicted by the presence of an asymmetric center. Though an asymmetric carbon atom is a very important aspect in determining the chirality of a molecule, it is not the only factor determining chirality. Several ring structures also show axial chirality.

02

Asymmetric center of the first structure

The asymmetric carbon is marked with an asterisk.

Both structure a and b represent the same molecule. Structure b gives more clarity as it shows that the central carbon is bonded to four different groups. The four different groups are : CH2Br, NH2, CF3 and

03

Asymmetric centre of the second structure’

This structure has two asymmetric carbons marked with asterisk.

04

Asymmetric center of the third structure

This structure has three asymmetric carbons marked with asterisk.

05

Asymmetric center of the fourth structure

This structure has three asymmetric carbons marked with asterisk.

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.

Start your free trial

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

Question: For each pair, give the relationship between the two compounds. Making models will be helpful.

(a) (2R,3S)-2,3-dibromohexane and (2S,3R)-2,3-dibromohexane

(b) (2R,3S)-2,3-dibromohexane (2R,3R)-2,3-dibromohexane

(c)

(d)

(e)

(f)

(g)

(h)

(i)

Question: Draw all distinct stereoisomers for each structure. Show the relationships (enantiomers, diastereomers, etc.) between the isomers. Label any meso iosmers, and draw any mirror planes of symmetry.

(a) CH3 -CHCI-CHOH-COOH

(b) tartaric acid, HOOC-CHOH - CHOH-COOH

(c) HOOC -CHBr-CHOH- CHOH-COOH

(d)

(e)

Question: For each of the compounds described by the following names,

1. draw a three-dimensional representation

2. star (*) each chiral center

3. draw any planes of symmetry.

4. draw any enantiomer.

5. draw any diastereomers.

6. label each structure you have drawn as chiral or achiral

(a) (S)-2-chlorobutane

(b)(R)-1,1,2-trimethylcyclohexane

(c) (2R,3S)-2,3-dibromohexane

(d) (1R,2R)-1,2-dibromocyclohexane

(e) meso-hexane-3,4-diol,CH3CH2CH(OH)CH(OH)CH2 CH3

(f) ±-hexane-3,4-diol

Question. For each structure,

  1. Draw all the stereoisomers.
  2. Label each structure as chiral or achiral.
  3. Give the relationships between the stereoisomers (enantiomers, diastereomers).

Question: Draw three-dimensional representations of the following compounds. Which have asymmetric carbon atoms? Which have no asymmetric carbons but are chiral anyway? Use your models for parts (a) through (d) and any others that seem unclear.

(a) CICH = C = CHCI

1,3-dichloropropadiene

(b) CICH = C = CHCH3

1-chlorobuta-.1,2 diene

(c) CICH = C = CH =C(CH3)2

1-chloro-3-methyl uta-1,2-diene

(d) CICH = C = CH CH2

1-chlorobuta-.1,3-diene

(e)

(f)

(g)
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

Read Explanation

Kinetics

Read Explanation

Inorganic Chemistry

Read Explanation
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