General, Organic, & Biological Chemistry
General, Organic, & Biological Chemistry
3rd Edition
ISBN: 9780073511245
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 16, Problem 16.67P
Interpretation Introduction

(a)

Interpretation:

A compound that contains an acetal with the molecular formula C5H12O2 should be drawn.

Concept Introduction:

Addition of one molecule of alcohol to an aldehyde or ketone results in a hemiacetal. Here, the C=O double bond breaks and single bonds are formed. If the hemiacetal is acyclic, it is not stable. Acyclic hemiacetal reacts with a second alcohol molecule and forms acetal.

General, Organic, & Biological Chemistry, Chapter 16, Problem 16.67P , additional homework tip  1

Interpretation Introduction

(b)

Interpretation:

A compound that contains a hemiacetal with the molecular formula C5H12O2 should be drawn.

Concept Introduction:

Addition of one molecule of alcohol to an aldehyde or ketone results in a hemiacetal. Here, the C=O double bond breaks and single bonds are formed. If the hemiacetal is acyclic, it is not stable. Acyclic hemiacetal reacts with a second alcohol molecule and forms acetal.

General, Organic, & Biological Chemistry, Chapter 16, Problem 16.67P , additional homework tip  2

Interpretation Introduction

(c)

Interpretation:

A compound that contains two ethers with the molecular formula C5H12O2 should be drawn.

Concept Introduction:

Even though acetals contain C-O-R bond, acetals are not ethers. Acetals have 2 OR groups attached to a single C atom. But an ether has one O atom which is bonded to 2 carbons.

Interpretation Introduction

(d)

Interpretation:

A compound that contains an alcohol and ether, but is not a hemiacetal with the molecular formula C5H12O2 should be drawn.

Concept Introduction:

Addition of one molecule of alcohol to an aldehyde or ketone results in a hemiacetal. Here, the C=O double bond breaks and single bonds are formed. If the hemiacetal is acyclic, it is not stable. Acyclic hemiacetal reacts with a second alcohol molecule and forms acetal.

General, Organic, & Biological Chemistry, Chapter 16, Problem 16.67P , additional homework tip  3

Even though acetals contain C-O-R bond, acetals are not ethers. Acetals have 2 OR groups attached to a single C atom. But an ether has one O atom which is bonded to 2 carbons.

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Draw and show the full mechanism of how the molecule ((1E, 3E, 5E)-1-methoxyhepta-1,3,5-triene) is built using substitution and elimination reactions. You can start with an alkane of any carbon length with any number of leaving groups attached or with a alkoxide of any carbon length (conjugate base of an alcohol). Show each step and and explanation for each reaction. Also include why the reagents and solvents were picked and what other products can be expected.
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Chapter 16 Solutions

General, Organic, & Biological Chemistry

Ch. 16.5 - What product is formed when each carbonyl compound...Ch. 16.5 - Prob. 16.12PCh. 16.5 - Prob. 16.13PCh. 16.6 - What alcohol is formed when each compound is...Ch. 16.6 - Prob. 16.15PCh. 16.6 - Prob. 16.16PCh. 16.7 - Prob. 16.17PCh. 16.7 - Prob. 16.18PCh. 16.8 - Prob. 16.19PCh. 16.8 - Prob. 16.20PCh. 16.8 - Prob. 16.21PCh. 16.8 - Label the three acetals in solanine, the toxic...Ch. 16.8 - Prob. 16.23PCh. 16.8 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Prob. 16.26PCh. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Give an acceptable name for each ketone. a. b. c....Ch. 16 - Prob. 16.36PCh. 16 - Prob. 16.37PCh. 16 - Draw the structure corresponding to each name. a....Ch. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - Prob. 16.41PCh. 16 - Prob. 16.42PCh. 16 - Draw out the structure of benzaldehyde, including...Ch. 16 - Prob. 16.44PCh. 16 - Which compound in each pair has the higher boiling...Ch. 16 - Prob. 16.46PCh. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Consider the following ball-and-stick model....Ch. 16 - Prob. 16.57PCh. 16 - Prob. 16.58PCh. 16 - Prob. 16.59PCh. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - Prob. 16.65PCh. 16 - Prob. 16.66PCh. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Label the functional group(s) in each compound as...Ch. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - What acetal is formed when each aldehyde or ketone...Ch. 16 - What acetal is formed when each aldehyde or ketone...Ch. 16 - Prob. 16.75PCh. 16 - Prob. 16.76PCh. 16 - Prob. 16.77PCh. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81PCh. 16 - Prob. 16.82PCh. 16 - Prob. 16.83PCh. 16 - Answer each question about phenylacetaldehyde,...Ch. 16 - Prob. 16.85PCh. 16 - Prob. 16.86PCh. 16 - Prob. 16.87PCh. 16 - Prob. 16.88PCh. 16 - Three constitutional isomers of molecular formula...Ch. 16 - Identify A—C in the following reaction sequenceCh. 16 - Androsterone is a male sex hormone that controls...Ch. 16 - Prob. 16.92PCh. 16 - Prob. 16.93PCh. 16 - Prob. 16.94PCh. 16 - Prob. 16.95PCh. 16 - Paraldehyde, a hypnotic and sedative once commonly...Ch. 16 - Prob. 16.97PCh. 16 - Prob. 16.98PCh. 16 - Prob. 16.99CPCh. 16 - Prob. 16.100CP
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