menu
bartleby
search
close search
Hit Return to see all results
close solutoin list

Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see “Chemical Connections: A, B, AB, and O Blood Group Substances” in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.

BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

Solutions

Chapter
Section
BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 2, Problem 2.62P
Textbook Problem
24 views

Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see “Chemical Connections: A, B, AB, and O Blood Group Substances” in Chapter 25.

Chapter 2, Problem 2.62P, Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of

  1. (a) Draw the alternative chair conformations of L-fucose.
  2. (b) Which of them is more stable? Explain.

(a)

Interpretation Introduction

Interpretation:

The alternative chair conformations of L-fucose has to be drawn.

Concept Introduction:

Conformations of cyclohexane:

Cyclohexane has many conformations due to C-C rotation.  The main conformations of cyclohexane are chair, boat and twist-boat conformations.

The two interconvertible chair conformations are the lowest-energy conformations of cyclohexane.

In chair conformation, the six C-H bonds are in axial orientation and six C-H bonds are in equatorial orientation.

Bonds that are axial in one chair conformation becomes equatorial in the alternative chair conformation and vice versa.

The more stable chair conformation of a substituted cyclohexane is the one that minimizes diaxial steric interactions and therefore has large groups equatorial.

Explanation of Solution

Given data:

A planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing is shown below.

(b)

Interpretation Introduction

Interpretation:

Among the alternative chair conformations of L-fucose, the more stable conformation has to be given and the reason has to be explained.

Concept Introduction:

Conformations of cyclohexane:

Cyclohexane has many conformations due to C-C rotation.  The main conformations of cyclohexane are chair, boat and twist-boat conformations.

The two interconvertible chair conformations are the lowest-energy conformations of cyclohexane.

In chair conformation, the six C-H bonds are in axial orientation and six C-H bonds are in equatorial orientation.

Bonds that are axial in one chair conformation becomes equatorial in the alternative chair conformation and vice versa.

The more stable chair conformation of a substituted cyclohexane is the one that minimizes diaxial steric interactions and therefore has large groups equatorial.

Still sussing out bartleby?

Check out a sample textbook solution.

See a sample solution

The Solution to Your Study Problems

Bartleby provides explanations to thousands of textbook problems written by our experts, many with advanced degrees!

Get Started

Chapter 2 Solutions

Organic Chemistry
Show all chapter solutions
add
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Tetrodotoxin Tetrodotoxin is one of the most...Ch. 2.6 - Tetrodotoxin Tetrodotoxin is one of the most...Ch. 2.6 - Tetrodotoxin Tetrodotoxin is one of the most...Ch. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Indicate whether the compounds in each set are...Ch. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Assume for the purposes of this problem that to be...Ch. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Draw structural formulas for the cis and trans...Ch. 2 - Following are the alternative chair conformations...Ch. 2 - What structural feature of cycloalkanes makes cis,...Ch. 2 - Is cis, trans isomerism possible in alkanes?Ch. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - When cyclohexane is substituted by an ethynyl...Ch. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - In Problem 2.24, you drew structural formulas for...Ch. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Following is the structural formula and a...Ch. 2 - Following is the structural formula and a...

Additional Science Textbook Solutions

Find more solutions based on key concepts
Show solutions add
(a) Prepare a table like Table 21.1 for the following occurrence. You toss four coins into the air simultaneous...

Physics for Scientists and Engineers, Technology Update (No access codes included)

Ail "atherogenic diet" is high in all of the following except fiber cholesterol saturated fats trans fats

Nutrition: Concepts and Controversies - Standalone book (MindTap Course List)