×
Log in to StudySoup
Get Full Access to Organic Chemistry - 7 Edition - Chapter 6 - Problem 6.54
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 7 Edition - Chapter 6 - Problem 6.54

Already have an account? Login here
×
Reset your password

We now introduce the concept of an organic chemistry roadmap. An organic

Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote ISBN: 9781133952848 483

Solution for problem 6.54 Chapter 6

Organic Chemistry | 7th Edition

  • Textbook Solutions
  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Organic Chemistry | 7th Edition

4 5 1 279 Reviews
16
2
Problem 6.54

We now introduce the concept of an organic chemistry roadmap. An organic chemistryroadmap is a graphical representation of the different reactions that can be used to inter-convert functional groups in molecules. Comparing the organic chemistry roadmap to areal roadmap, the functional groups are analogous to cities and the reactions are the roadsbetween them. The power of the organic chemistry roadmap is that it helps students visu-alize how to interconvert key functional groups for use in multistep syntheses problems.It also will be a useful place for you to keep track of the reactions we encounter in futureTo make your own roadmap, take a blank full sheet of paper and write the following func-tional groups in the orientations shown. Fill the entire sheet of paper and leave plenty ofroom between functional groups. Most students finRefer to the Key Reactions section at the end of this chapter. Draw arrows betweenfunctional groups to account for each reaction. Write the reagents required to bringabout each reaction next to the arrow. Next, record any regiochemistry or stereochemistryconsiderations relevant to the reaction, such as Markovnikov regiochemistry or antiaddition stereochemistry. You should also record any key aspects of the mechanism, suchas formation of a carbocation intermediate, as a helpful reminder. On the above organicchemistry roadmap template, the information for the first reaction, hydrohalogenationof an alkene, has been added to help you get started. For this initial roadmap, do notwrite an arrow for reaction 10, enantioselective reduction, because it is of a highly specificnature and a roadmap is intended to organize reactions that are of more general use.Note that the roadmap template applies to Chapters 611, so you will not use all of thefunctional groups listed until you are finished with Chapter 11. Appendix 11 containsa series of roadmaps for different sections of the book, but you should use those forreference only after you have completed your own.d it helpful to use a poster-sized sheetof paper filled out in landscape orientation.

Step-by-Step Solution:
Step 1 of 3

1. Chemical equations for reactions R­MgX + HX ­­> R­H + MgX2 2. Why do you need to clean the surface of Mg Fresh Mg surface is essential for the Grignard synthesis 3. Usage of drying tube The septum and drying tube prevent atmospheric moisture from entering into the apparatus The drying tube protects the Grignard from oxygen 4. What’s the main impurities and how to remove that Biphenyl, adding NaOH will cause biphenyl and benzene to remain in the ether layer 5. What kind of things will ruin the reaction Moisture, oxygen, water 6. How we purify the product including the usage of NaOH and HCl second time HCl is added first to react with Mg and move any other inorganic contaminants to the water layer. Next, NaOH is added to cause the benzoic acid to be more soluble in the aqueous layer and benzene and biphenyl are nonpolar and remain in the ether layer. Finally HCl is added back to the aqueous layer to cause benzoic acid to precipitate out 7. Safety Diethyl ether is extremely flammable. Ether fumes are denser than air and can creep along benchtops to ignitions sources. Do not leave containers/flasks with ether in them open. Use a cap or stopper What kind of bonds do Grignard reactions form Carbon­carbon  What grignard reagent do you form phenylmagnesium bromide. From magnesium and bromobenzene  Describe the outline of the grignard experiment Magnesium and bromobenzene combine to make phenylmagnesium bromide. This is added to CO2 to make benzoate. Hyrolysis gives benzoic acid.  How is the grignard reagent formed

Step 2 of 3

Chapter 6, Problem 6.54 is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 7
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
ISBN: 9781133952848

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

We now introduce the concept of an organic chemistry roadmap. An organic