
Concept explainers
Interpretation:
The oxidizing or reducing agents that would be used to carry out each of the given transformation is to be determined.
Concept introduction:
Swern oxidation reaction converts primary and secondary alcohols into
Reduction of carbonyl compounds to hydrocarbons is achieved by treating carbonyl compounds with lithium aluminum hydride
Sodium borohydride
Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to
Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid, and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.
Potassium permanganate: It is a strong oxidation agent that converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.
When oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols or form carboxylic acids from aldehydes. Compounds with no hydrogen atom attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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Chapter 12 Solutions
Organic Chemistry
- Assign all the protonsarrow_forwardAssign all the carbonsarrow_forward9 7 8 C 9 8 200 190 B 5 A -197.72 9 8 7 15 4 3 0: ང་ 200 190 180 147.52 134.98 170 160 150 140 130 120 110 100 90 90 OH 10 4 3 1 2 -143.04 140. 180 170 160 150 140 130 120 110 100 90 CI 3 5 1 2 141.89 140.07 200 190 180 170 160 150 140 130 120 110 100 ៖- 90 129. 126.25 80 70 60 -60 50 40 10 125.19 -129.21 80 70 3.0 20 20 -8 60 50 10 ppm -20 40 128.31 80 80 70 60 50 40 40 -70.27 3.0 20 10 ppm 00˚0-- 77.17 30 20 20 -45.36 10 ppm -0.00 26.48 22.32 ―30.10 ―-0.00arrow_forward
- Assign all the carbonsarrow_forwardC 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00arrow_forwardCurved arrows were used to generate the significant resonance structure and labeled the most significant contribute. What are the errors in these resonance mechanisms. Draw out the correct resonance mechanisms with an brief explanation.arrow_forward
- What are the: нсе * Moles of Hice while given: a) 10.0 ml 2.7M ? 6) 10.ome 12M ?arrow_forwardYou are asked to use curved arrows to generate the significant resonance structures for the following series of compounds and to label the most significant contributor. Identify the errors that would occur if you do not expand the Lewis structures or double-check the mechanisms. Also provide the correct answers.arrow_forwardhow to get limiting reactant and % yield based off this data Compound Mass 6) Volume(mL Ben zaphone-5008 ne Acetic Acid 1. Sam L 2-propanot 8.00 Benzopin- a col 030445 Benzopin a Colone 0.06743 Results Compound Melting Point (°c) Benzopin acol 172°c - 175.8 °c Benzoping to lone 1797-180.9arrow_forward
- Assign ALL signals for the proton and carbon NMR spectra on the following pages.arrow_forward7.5 1.93 2.05 C B A 4 3 5 The Joh. 9 7 8 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 0.86 OH 10 4 3 5 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 CI 4 3 5 1 2 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 2.21 4.00 1.5 2.00 2.07 1.0 ppm 2.76arrow_forwardAssign the functional group bands on the IR spectra.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co

