Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 10, Problem 10.48P

(a)

Interpretation Introduction

Interpretation:

The strength of Hydrogen bonding associated by O-H and N-H bonds has to be compared.

Concept Introduction:

Physical properties of ethers: Ethers are polar molecules in which Oxygen bears a partial negative charge and each attached to carbon bears a partial positive charge. Only weak dipole-dipole interactions exist between ether molecules in the liquid form. As ethers do not form hydrogen bonding are less soluble in water. Due to the presence of lone pairs on oxygen atom can act as hydrogen bond acceptors that makes them more water-soluble than hydrocarbons of comparable molecular weight.

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Boiling point: The temperature at which a liquid boils and turns into gas phase is known as boiling point.

(b)

Interpretation Introduction

Interpretation:

The boiling pointof the compounds associated by O-H and N-H bonds has to be compared.

Concept Introduction:

Physical properties of ethers: Ethers are polar molecules in which Oxygen bears a partial negative charge and each attached to carbon bears a partial positive charge. Only weak dipole-dipole interactions exist between ether molecules in the liquid form. As ethers do not form hydrogen bonding are less soluble in water. Due to the presence of lone pairs on oxygen atom can act as hydrogen bond acceptors that makes them more water-soluble than hydrocarbons of comparable molecular weight.

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Boiling point: The temperature at which a liquid boils and turns into gas phase is known as boiling point.

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Students have asked these similar questions
TRUE OR FALSE (a) There are three amines with the molecular formula C3H9N. (b) Aldehydes, ketones, carboxylic acids, and esters all contain a carbonyl group. (c) A compound with the molecular formula of C3H6O may be either an aldehyde, a ketone, or a carboxylic acid. (d) Bond angles about the carbonyl carbon of an aldehyde, a ketone, a carboxylic acid, and an ester are all approximately 109.5°. (e) The molecular formula of the smallest aldehyde is C3H6O, and that of the smallest ketone is also C3H6O. (f) The molecular formula of the smallest carboxylic acid is C2H4O2.
Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the following compounds:(a) Penicillin G is a naturally occurring antibiotic.(b) Dopamine is the neurotransmitter that is deficient in Parkinson’s disease.(c) Capsaicin gives the fiery taste to chili peppers.(d) Thyroxine is the principal thyroid hormone.(e) Testosterone is a male sex hormone.
Identify which of the following statement(s) is/are true. (f) Aldehydes, ketones, carboxylic acids, and esters all contain a carbonyl group. (g) A compound with the molecular formula of C3H6O may be either an aldehyde, a ketone, or a carboxylic acid. (h) Bond angles about the carbonyl carbon of an aldehyde, a ketone, a carboxylic acid, and an ester are all approximately 109.5°. (i) The molecular formula of the smallest aldehyde is C3H6O, and that of the smallest ketone is also C3H6O. (j) The molecular formula of the smallest carboxylic acid is C2H4O2.

Chapter 10 Solutions

Organic Chemistry

Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
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