Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305082144
Author: John E. McMurry
Publisher: Cengage Learning
bartleby

Concept explainers

Question
Book Icon
Chapter 14.SE, Problem 27AP
Interpretation Introduction

a) 1 mol Br2 in CH2Cl2

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH2Cl2 are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH2Cl2 undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH2Cl2.

Expert Solution
Check Mark

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH2Cl2 are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH2Cl2 it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH2Cl2 are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  3

Interpretation Introduction

b) O3 followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution
Check Mark

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution
Check Mark

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution
Check Mark

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  12

Interpretation Introduction

e) 3-Buten-2-one (H2C=CHCOCH3)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution
Check Mark

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  15

Interpretation Introduction

f) Excess OsO4, followed by NaHSO3

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO4 and then with NaHSO3 is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO4, a single step addition of OsO4 to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO3 yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO4 and then with NaHSO3.

Expert Solution
Check Mark

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO4 and then with NaHSO3 is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO4 the addition of OsO4 takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO3 to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO4 and then with NaHSO3 is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip  18

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity
Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**
11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

Chapter 14 Solutions

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th

Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
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