Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
Question
Book Icon
Chapter 17, Problem 17.71P
Interpretation Introduction

(a)

Interpretation:

The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.

Concept Introduction:

Hemiacetal is a molecule formed by the addition of an alcohol to an aldehyde or ketone,containing a carbon bonded to one −OH group and one −OR group. For example-

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  1

Expert Solution
Check Mark

Answer to Problem 17.71P

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  2

Explanation of Solution

Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  3

Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  4

Interpretation Introduction

(b)

Interpretation:

The number of possible stereoisomers of 5-hydroxyhexanal should be determined.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution
Check Mark

Answer to Problem 17.71P

5-hydroxyhexanal has 2 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  5

In 5-hydroxyhexanal, there is one stereocenter.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n= 21= 2

Thus, number of stereoisomers will be 2.

Interpretation Introduction

(c)

Interpretation:

The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.

Concept Introduction:

Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Expert Solution
Check Mark

Answer to Problem 17.71P

Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.

Explanation of Solution

For a molecule with n stereoisomers, a maximum of 2n stereoisomers are possible.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.71P , additional homework tip  6

In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.

Therefore, number of stereoisomers can be calculated as follows:

Number of stereOisOmers = 2n= 22= 4

Thus, number of stereoisomers are 4.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Identifying the major species in weak acid or weak base equilibria Your answer is incorrect. • Row 2: Your answer is incorrect. • Row 3: Your answer is incorrect. • Row 6: Your answer is incorrect. 0/5 The preparations of two aqueous solutions are described in the table below. For each solution, write the chemical formulas of the major species present at equilibrium. You can leave out water itself. Write the chemical formulas of the species that will act as acids in the 'acids' row, the formulas of the species that will act as bases in the 'bases' row, and the formulas of the species that will act as neither acids nor bases in the 'other' row. You will find it useful to keep in mind that HF is a weak acid. acids: HF 0.1 mol of NaOH is added to 1.0 L of a 0.7M HF solution. bases: 0.13 mol of HCl is added to 1.0 L of a solution that is 1.0M in both HF and KF. Exponent other: F acids: HF bases: F other: K 1 0,0,... ? 000 18 Ar
Using reaction free energy to predict equilibrium composition Consider the following equilibrium: 2NOCI (g) 2NO (g) + Cl2 (g) AGº =41. kJ Now suppose a reaction vessel is filled with 4.50 atm of nitrosyl chloride (NOCI) and 6.38 atm of chlorine (C12) at 212. °C. Answer the following questions about this system: ? rise Under these conditions, will the pressure of NOCI tend to rise or fall? x10 fall Is it possible to reverse this tendency by adding NO? In other words, if you said the pressure of NOCI will tend to rise, can that be changed to a tendency to fall by adding NO? Similarly, if you said the pressure of NOCI will tend to fall, can that be changed to a tendency to rise by adding NO? yes no If you said the tendency can be reversed in the second question, calculate the minimum pressure of NO needed to reverse it. Round your answer to 2 significant digits. 0.035 atm ✓ G 00. 18 Ar
Highlight each glycosidic bond in the molecule below. Then answer the questions in the table under the drawing area. HO- HO- -0 OH OH HO NG HO- HO- OH OH OH OH NG OH

Chapter 17 Solutions

Introduction to General, Organic and Biochemistry

Ch. 17 - 17-11 What is the difference in structure between...Ch. 17 - 17-12 Is it possible for the carbon atom of a...Ch. 17 - 17-13 Which compounds contain carbonyl groups?Ch. 17 - 17-14 Following are structural formulas for two...Ch. 17 - 17-15 Draw structural formulas for the four...Ch. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - 17-18 Draw structural formulas for these ketones....Ch. 17 - 17-19 Write the JUPAC names for these compounds.Ch. 17 - Prob. 17.20PCh. 17 - 17-2 1 Explain why each name is incorrect. Write...Ch. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - 17-24 In each pair of compounds, select the one...Ch. 17 - Prob. 17.25PCh. 17 - 17-26 Account for the fact that acetone has a...Ch. 17 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 17 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 17 - 17-29 Why can’t two molecules of acetone form a...Ch. 17 - 17-30 Answer true or false. (a) The reduction of...Ch. 17 - 17-3 1 Draw a structural formula for the principal...Ch. 17 - Prob. 17.32PCh. 17 - 17-33 What simple chemical test could you use to...Ch. 17 - 17-34 Explain why liquid aldehydes are often...Ch. 17 - 17-35 Suppose that you take a bottle of...Ch. 17 - 17-36 Explain why the reduction of an aldehyde...Ch. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - 17-47 What is the characteristic structural...Ch. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - 17-54 Following is the structure of...Ch. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - 17-60 1-Propanol can be prepared by the reduction...Ch. 17 - Prob. 17.61PCh. 17 - 17-62 Show how to bring about these conversions....Ch. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - 17-67 Draw structural formulas for these...Ch. 17 - Prob. 17.68PCh. 17 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 17 - 17-70 What simple chemical test could you use to...Ch. 17 - Prob. 17.71PCh. 17 - 17-72 The following molecule is an enediol; each...Ch. 17 - 17-73 Alcohols can be prepared by the...Ch. 17 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - 17-78 Complete the following equation for these...Ch. 17 - 17-79 Write an equation for each conversion. (a)...
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning