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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
BuyFind

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

Solutions

Chapter 17, Problem 17.9P
Textbook Problem

17-9 Answer true or false.

(a) The one aldehyde and the one ketone with a molecular formula of C3H6O are constitutional isomers.

(b) Aldehydes and ketones both contain a carbonyl group.

(c) The VSEPR model predicts bond angles of 1200 about the carbonyl carbon of aldehydes and ketones.

(d) The carbonyl carbon of a ketone is a stereocenter.

Expert Solution

(a)

Interpretation Introduction

Interpretation:

Answer true or false for the following statement.

The one aldehyde and one ketone with a molecular formula of C3H6O are constitutional isomers.

Concept Introduction:

Constitutional isomers have the same molecular formula but different structural formulas or connectivity with atoms is different. In aldehydes, the carbonyl group is bonded to a hydrogen atom and ketones carbonyl group is bonded to two carbon atoms.

Answer to Problem 17.9P

The one aldehyde and one ketone with a molecular formula of C3H6O are constitutional isomers is the true statement.

Explanation of Solution

The given molecular formula: C3H6O

For this molecular formula we can draw both aldehyde and ketone. They are as follows.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.9P , additional homework tip  1

From the above structures aldehydes and ketones having same molecular formula are constitutional isomers.

Therefore, the given statement is true.

Expert Solution

(b)

Interpretation Introduction

Interpretation:

Answer true or false for the following statement.

Aldehydes and ketones both contain a carbonyl group.

Concept Introduction:

In aldehydes, the carbonyl group is bonded to a hydrogen atom and ketones carbonyl group is bonded to two carbon atoms.

Answer to Problem 17.9P

Aldehydes and ketones both contain a carbonyl group is true statement.

Explanation of Solution

In aldehydes, the carbonyl group is bonded to a hydrogen atom and in ketone carbonyl group is bonded to two carbon atoms. Hence, both an aldehyde and a ketone have a carbonyl group.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.9P , additional homework tip  2

Where, R is an alkyl group.

Therefore, the given statement is true.

Expert Solution

(c)

Interpretation Introduction

Interpretation:

Answer true or false for the following statement.

The VSEPR model predicts bond angles of 1200 about the carbonyl carbon of aldehydes and ketones.

Concept Introduction:

In aldehydes, the carbonyl group is bonded to a hydrogen atom and ketones carbonyl group is bonded to two carbon atoms. VSEPR model predicts the geometry of the molecule with the help of number of pair of electrons present around the central atoms and bond angle of the molecule.

Answer to Problem 17.9P

The VSEPR model predicts bond angles of 1200 about the carbonyl carbon if aldehydes and ketones is the true statement.

Explanation of Solution

In aldehydes, the carbonyl group is bonded to a hydrogen atom and ketones carbonyl group is bonded to two carbon atoms. The carbonyl group of aldehyde and ketone are represented are as follows.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.9P , additional homework tip  3

According to VSEPR theory, three pair of electron groups forms a Trigonal planar geometry with bond angle of 1200.

Therefore, the given statement is true.

Expert Solution

(d)

Interpretation Introduction

Interpretation:

Answer true or false for the following statement.

The carbonyl carbon of ketone is a stereocentre.

Concept Introduction:

A stereocentre is a tetrahedral carbon atom in which four different groups are attached to it. When an atom generally carbon is linked with four different groups, then that centre is known as chiral centre.

Answer to Problem 17.9P

The carbonyl carbon of ketone is a stereocenter is the false statement.

Explanation of Solution

In aldehydes, the carbonyl group is bonded to a hydrogen atom and in ketone carbonyl group is bonded to two carbon atoms. The carbonyl group of aldehyde and ketone are represented are as follows.

Introduction to General, Organic and Biochemistry, Chapter 17, Problem 17.9P , additional homework tip  4

In ketones, the carbonyl carbon is boded to carbonyl oxygen by a double bond group and bonded to two other carbon atoms.

Therefore, the given statement is false.

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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 - 17-16 Answer true or false. (a) An aldehyde is...Ch. 17 - 17-17 Draw structural formulas for these...Ch. 17 - 17-18 Draw structural formulas for these ketones....Ch. 17 - 17-19 Write the JUPAC names for these compounds.Ch. 17 - 17-20 Write the IUPAC names for these compounds.Ch. 17 - 17-2 1 Explain why each name is incorrect. Write...Ch. 17 - 17-22 Explain why each name is incorrect. Write...Ch. 17 - 17-23 Answer true or false. (a) Aldehydes and...Ch. 17 - 17-24 In each pair of compounds, select the one...Ch. 17 - 17-25 Acetone is completely soluble in water, but...Ch. 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 - 17-32 Draw a structural formula for the principal...Ch. 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 - 17-37 Write a structural formula for the principal...Ch. 17 - 17-38 Draw a structural formula for the principal...Ch. 17 - 17-39 1, 3-Dihydroxy-2-propanone, more commonly...Ch. 17 - 17-40 Draw a structural formula for the product...Ch. 17 - 17-41 Draw a structural formula for the product...Ch. 17 - 17-42 Mark each statement true or false. (a) Keto...Ch. 17 - 17-43 Which of these compounds undergo keto-enol...Ch. 17 - 17-44 Draw all enol forms of each aldehyde and...Ch. 17 - 17-45 Draw a structural formula for the keto form...Ch. 17 - 17-46 Warfarin is widely used in medicine as a...Ch. 17 - 17-47 What is the characteristic structural...Ch. 17 - 17-48 Which compounds are hemiacetals, which are...Ch. 17 - 17-49 Which compounds are hemiacetals, which are...Ch. 17 - 17-50 Draw the hemiacetal and then the acetal...Ch. 17 - 17-51 Draw the structures of the aldehydes or...Ch. 17 - 17-52 The following compound is a component of the...Ch. 17 - 17-53 Consider the formation of an acetal. If the...Ch. 17 - 17-54 Following is the structure of...Ch. 17 - 17-55 What is the difference in meaning between...Ch. 17 - 17-56 What is the difference in meaning between...Ch. 17 - 17-57 List the reagents and experimental...Ch. 17 - 17-58 Draw a structural formula for an aldehyde or...Ch. 17 - 17-59 Draw a structural formula for an aldehyde or...Ch. 17 - 17-60 1-Propanol can be prepared by the reduction...Ch. 17 - 17-61 Show how to bring about these conversions....Ch. 17 - 17-62 Show how to bring about these conversions....Ch. 17 - 17-63 Describe a simple chemical test by which you...Ch. 17 - 17-64 Mark the aldehyde or ketone group in these...Ch. 17 - 17-65 Draw a structural formula for the product...Ch. 17 - 17-66 Draw structural formulas for the (a) one...Ch. 17 - 17-67 Draw structural formulas for these...Ch. 17 - 17-68 Why does acetone have a lower boiling point...Ch. 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 - 17-71 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 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 - 17-75 Ribose, C5H10O5, contains an aldehyde group...Ch. 17 - 17-76 Name the functional groups in each steroid...Ch. 17 - 17-77 Sodium borohydride is a laboratory reducing...Ch. 17 - 17-78 Complete the following equation for these...Ch. 17 - 17-79 Write an equation for each conversion. (a)...

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