EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
Question
Book Icon
Chapter 10.4, Problem 20P

(a)

Interpretation Introduction

Interpretation:

The constitutional isomer, which is formed greatest yield in the given reaction should be given.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid is known as dehydration reaction, for example

EBK ORGANIC CHEMISTRY, Chapter 10.4, Problem 20P , additional homework tip  1

Alcohols are react with acids like hydrochloric acid or hydrobromic to yields the corresponding carbocation intermediates, this carbocation intermediate undergoes elimination reaction to give a corresponding alkene as a product.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

Cis–trans isomerism (or) geometric isomerism or configurational isomerism:

The functional groups are in the same side of the carbon chain is called cis isomer.

The functional groups are in opposite to each other in the carbon chain is called trans isomer.

Two similar functional groups are in same side which is called as Z-isomer.

Two similar functional groups are opposite side which is called as E-isomer.

Stereoisomers: same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space.

(b)

Interpretation Introduction

Interpretation:

The stereoisomer, which is formed greatest yield in the given reaction should be given.

Concept introduction:

Dehydration reaction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid is known as dehydration reaction, for example

EBK ORGANIC CHEMISTRY, Chapter 10.4, Problem 20P , additional homework tip  2

Alcohols are react with acids like hydrochloric acid or hydrobromic to yields the corresponding carbocation intermediates, this carbocation intermediate undergoes elimination reaction to give a corresponding alkene as a product.

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

Cis–trans isomerism (or) geometric isomerism or configurational isomerism:

The functional groups are in the same side of the carbon chain is called cis isomer.

The functional groups are in opposite to each other in the carbon chain is called trans- isomer.

Two similar functional groups are in same side which is called as Z-isomer.

Two similar functional groups are opposite side which is called as E-isomer.

Stereoisomers: same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space.

Blurred answer
Students have asked these similar questions
Which molecules A through D shown below would, upon hydrogenation of the double bond with H2 and Pd-carbon, give a mixture of enantiomers? CH3 в H3C-c=c-cH3 H,C- - CgHs D O 1. Only D. O 2. Molecules A and C. O 3. Only A. O 4. Molecules B and C.
4. What are the products formed when each alkene below is treated first with MCPBA in CH2CI2 solvent followed in a second step by treatment with NaOH?. Are the final products ( of the second step) meso or formed as a racemic mixture?
Aa.64.

Chapter 10 Solutions

EBK ORGANIC CHEMISTRY

Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY