GENERAL,ORGANIC,+BIOCHEMISTRY
GENERAL,ORGANIC,+BIOCHEMISTRY
10th Edition
ISBN: 9781260148954
Author: Denniston
Publisher: RENT MCG
Question
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Chapter 13, Problem 4MCP

(a)

Interpretation Introduction

Interpretation:

The statement “2-pentanone is a primary ketone” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(a)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

2-pentanone or methyl propyl ketone is primary ketone with carbonyl group at the second position.  The structure is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  1

Hence, the statement 2-pentanone is a primary ketone is true.

(b)

Interpretation Introduction

Interpretation:

The statement “2-pentanone has a higher melting point than 2-pentanol” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(b)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is false because 2-pentanone has lower melting point than 2-pentanol due to the presence of weak intermolecular hydrogen bonding in the former.

Explanation of Solution

2-pentanone is a ketone and 2-pentanol is an alcohol.

Alcohols have strong intermolecular hydrogen bonding.  The OH group present in the alcohol allows the molecules to engage in hydrogen bonding.  A larger amount of energy is required to break the intermolecular hydrogen bonding in alcohols hence, they have higher boiling and higher melting points.

Ketones have lower boiling points when compared to alcohols, representing the presence of weak intermolecular dipole-dipole forces.  Due to weaker intermolecular hydrogen and weaker dipole-dipole attractions in ketones, they have lower boiling points compared to alcohols.

Hence, the given statement is false because 2-pentanone has lower melting point than 2-pentanol due to the presence of weak intermolecular hydrogen bonding in the former.

(c)

Interpretation Introduction

Interpretation:

The statement “2-pentanone forms hydrogen bonds with water” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(c)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

2-pentanone can form hydrogen bonds with water.  The hydrogen bonds are formed through their oxygen atoms to the hydrogen atoms of water.  Thus, they are reasonably water-soluble.  Hence, the given statement is true.

(d)

Interpretation Introduction

Interpretation:

The statement “2-pentanone is nonpolar” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(d)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is false because 2-pentanone is polar.

Explanation of Solution

The structure of 2-pentanone is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  2

The carbonyl group present in 2-pentanone is polar in nature and thereby can participate in dipole-dipole attractions.  Therefore, 2-pentanone is polar in nature.

The statement “2-pentanone is nonpolar” is false due to the presence of polar carbonyl group in them; 2-pentanone is polar in nature.

(e)

Interpretation Introduction

Interpretation:

The statement “2-pentanone has a molecular formula of C5H9OH” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(e)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

The structure of 2-pentanone is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  3

From the structure of 2-pentanone, it can be seen that 2-pentanone comprises of five carbon atoms, ten hydrogen atoms and one oxygen atom.  The molecular formula of 2-pentanone is C5H10O.  It can also be written as C5H9OH.

The statement “2-pentanone has a molecular formula of C5H9OH” is true.

(f)

Interpretation Introduction

Interpretation:

The statement “2-pentanone has a higher boiling point than hexane” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(f)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

The presence of polar carbonyl group and the attractive forces between the carbonyl-containing compounds include London dispersion forces between the hydrocarbon chains and dipole-dipole attractions between the carbonyl groups.  Because the dipole-dipole attractions between the molecules are stronger than London dispersion forces, 2-pentanone has higher boiling point than hexane.  Hence, the given statement is true.

(g)

Interpretation Introduction

Interpretation:

The statement “2-pentanone is a liquid at room temperature” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(g)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

2-pentanone is clear colorless liquid with the odor of fingernail polish.  It is less dense than water and soluble in water.  It is found in apple and a few other plant sources.  Hence, the statement “2-pentanone is a liquid at room temperature” is true.

(h)

Interpretation Introduction

Interpretation:

The statement “2-pentanone is water soluble” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(h)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

Ketones cannot form hydrogen bonds with each other, but they form intermolecular hydrogen bonds with water.  As a result, the smaller members of ketones (five or fewer carbon atoms) are soluble in water.  Hence, the statement “2-pentanone is a water soluble” is true.

(i)

Interpretation Introduction

Interpretation:

The statement “2-pentanone has a carbonyl functional group” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(i)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

Ketone is carbonyl compounds.  The carbonyl group of the ketone is polar and can participate in dipole-dipole attractions.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  4

The structure of 2-pentanone is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  5

2-pentanone shows the presence of carbonyl group.  Hence, the statement “2-pentanone has a carbonyl functional group” is true because it consists of polar carbonyl group.

(j)

Interpretation Introduction

Interpretation:

The statement “2-pentanone is a structural isomer of pentanal” has to be predicted as true or false.  If the statement is false, the reason for the false statement has to be described.

(j)

Expert Solution
Check Mark

Answer to Problem 4MCP

The given statement is true.

Explanation of Solution

Structural isomers are those with same molecular formula but differ in arrangement of atoms.

The molecular formula of 2-pentanone is C5H10O and its structure is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  6

The molecular formula of pentanal is C5H10O and its structure is,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 13, Problem 4MCP , additional homework tip  7

Both these are structural isomers with each other and hence, the statement “2-pentanone is a structural isomer of pentanal” is true.

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Chapter 13 Solutions

GENERAL,ORGANIC,+BIOCHEMISTRY

Ch. 13.2 - Prob. 13.7QCh. 13.2 - Write the condensed formula for each of the...Ch. 13.3 - Draw the structure of the aldehyde synthesized...Ch. 13.3 - Prob. 13.10QCh. 13.4 - Prob. 13.5PPCh. 13.4 - Prob. 13.6PPCh. 13.4 - Prob. 13.7PPCh. 13.4 - Prob. 13.8PPCh. 13.4 - Prob. 13.11QCh. 13.4 - Prob. 13.12QCh. 13.4 - Identify each of the following structures as a...Ch. 13.4 - Identify each of the following structures as a...Ch. 13.4 - Prob. 13.9PPCh. 13 - Prob. 13.15QPCh. 13 - Prob. 13.16QPCh. 13 - Prob. 13.17QPCh. 13 - Prob. 13.18QPCh. 13 - Prob. 13.19QPCh. 13 - Prob. 13.20QPCh. 13 - Prob. 13.21QPCh. 13 - Why do hydrocarbons have lower boiling points than...Ch. 13 - Prob. 13.23QPCh. 13 - Prob. 13.24QPCh. 13 - Prob. 13.25QPCh. 13 - Prob. 13.26QPCh. 13 - Prob. 13.27QPCh. 13 - Prob. 13.28QPCh. 13 - Draw each of the following using condensed...Ch. 13 - Prob. 13.30QPCh. 13 - Prob. 13.31QPCh. 13 - Prob. 13.32QPCh. 13 - Prob. 13.33QPCh. 13 - Prob. 13.34QPCh. 13 - Prob. 13.35QPCh. 13 - Prob. 13.36QPCh. 13 - Prob. 13.37QPCh. 13 - Prob. 13.38QPCh. 13 - Give the IUPAC name for each of the following...Ch. 13 - Give the IUPAC name for each of the following...Ch. 13 - Prob. 13.41QPCh. 13 - Prob. 13.42QPCh. 13 - Prob. 13.43QPCh. 13 - Prob. 13.44QPCh. 13 - Prob. 13.45QPCh. 13 - Prob. 13.46QPCh. 13 - Prob. 13.47QPCh. 13 - Prob. 13.48QPCh. 13 - Prob. 13.49QPCh. 13 - Prob. 13.50QPCh. 13 - Prob. 13.51QPCh. 13 - Prob. 13.52QPCh. 13 - Prob. 13.53QPCh. 13 - Prob. 13.54QPCh. 13 - Prob. 13.55QPCh. 13 - Prob. 13.56QPCh. 13 - Prob. 13.57QPCh. 13 - Prob. 13.58QPCh. 13 - Prob. 13.59QPCh. 13 - Prob. 13.60QPCh. 13 - Prob. 13.61QPCh. 13 - An unknown has been determined to be one of the...Ch. 13 - Prob. 13.63QPCh. 13 - Prob. 13.64QPCh. 13 - Prob. 13.65QPCh. 13 - Prob. 13.66QPCh. 13 - Which of the following compounds would be expected...Ch. 13 - Write an equation representing the reaction of...Ch. 13 - Prob. 13.69QPCh. 13 - Prob. 13.70QPCh. 13 - Prob. 13.71QPCh. 13 - Prob. 13.72QPCh. 13 - Prob. 13.73QPCh. 13 - Prob. 13.74QPCh. 13 - Prob. 13.75QPCh. 13 - Prob. 13.76QPCh. 13 - Prob. 13.77QPCh. 13 - Prob. 13.78QPCh. 13 - Prob. 13.79QPCh. 13 - Prob. 13.80QPCh. 13 - Prob. 13.81QPCh. 13 - Prob. 13.82QPCh. 13 - Prob. 13.83QPCh. 13 - Prob. 13.84QPCh. 13 - Prob. 1MCPCh. 13 - Prob. 2MCPCh. 13 - Prob. 3MCPCh. 13 - Prob. 4MCPCh. 13 - Prob. 6MCPCh. 13 - Prob. 7MCPCh. 13 - Prob. 8MCPCh. 13 - Design a synthesis for each of the following...Ch. 13 - Prob. 10MCPCh. 13 - Prob. 12MCP
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