AUCHE 252 - Organic Chemistry II
- Page ID
- 469352
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)- 2: 1H NMR
- In Chapter 12, you learned how an organic chemist could use two spectroscopic techniques, mass spectroscopy and infrared spectroscopy, to assist in determining the structure of an unknown compound. This chapter introduces a third technique, nuclear magnetic resonance (NMR). The two most common forms of NMR spectroscopy, ¹H NMR and ¹³C NMR, will be discussed, the former in much more detail than the latter.
- 2.1: Index of Hydrogen Deficiency (IHD)
- 2.2: Nuclear Magnetic Resonance Spectroscopy
- 2.3: The Nature of NMR Absorptions
- 2.4: Chemical Shifts
- 2.5: Chemical Shifts in ¹H NMR Spectroscopy
- 2.6: Integration of ¹H NMR Absorptions- Proton Counting
- 2.7: Spin-Spin Splitting in ¹H NMR Spectra
- 2.8: ¹H NMR Spectroscopy and Proton Equivalence
- 2.9: More Complex Spin-Spin Splitting Patterns
- 2.10: Uses of ¹H NMR Spectroscopy
- 3: Alcohols and Ethers
- In this unit, we examine the chemistry of the alcohol family of compounds. Alcohols can undergo a wide variety of reactions, and because of this reactivity and because they can be prepared in a number of different ways, alcohols occupy an important position in organic chemistry. The discussion begins with an outline of the nomenclature of alcohols and phenols. We review the physical properties of these compounds, and discuss methods used to obtain the lower members on an industrial scale.
- 3.1: Preparing Ethers
- 3.2: Crown Ethers
- 3.3: Reactions of Ethers- Acidic Cleavage
- 3.4: Cyclic Ethers - Epoxides
- 3.5: Reactions of Epoxides- Ring-opening
- 3.6: Nomenclature of Alcohols
- 3.7: Reactions of Alcohols
- 3.8: Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3
- 3.9: Protecting Groups in Organic Synthesis
- 5: Aldehydes and Ketones
- Alpha-substitution reactions are the third major type of reaction that you will study in your investigation of the chemistry of carbonyl compounds. As you will see, these reactions proceed through the formation of the enol form of the carbonyl compound. After a brief review of keto-enol tautomerism, we begin our discussion of alpha-substitution reactions by looking at the methods used to introduce a halogen atom into a carbonyl-containing compound—reactions.
- 5.1: Keto-Enol Tautomerism
- 5.2: Reactivity of Enols- The Mechanism of Alpha-Substitution Reactions
- 5.3: Alpha Halogenation of Aldehydes and Ketones
- 5.4: Reactivity of Enolate Ions
- 5.5: Alkylation of Enolate Ions
- 5.6: Carbonyl Condensations - The Aldol Reaction
- 5.7: Carbonyl Condensations versus Alpha Substitutions
- 5.8: Dehydration of Aldol Products - Synthesis of Enones
- 5.9: Mixed Aldol Reactions
- 5.10: Intramolecular Aldol Reactions
- 5.11: Nucleophilic Addition of Water- Hydration
- 5.12: Nucleophilic Addition of Alcohols- Acetal Formation
- 5.13: Nucleophilic Addition of Amines- Imine and Enamine Formation
- 6: Carboxylic Acid Derivatives
- The compounds discussed in this chapter are all considered to be derived from carboxylic acids, and include acid halides, acid anhydrides, esters and amides (thioesters and acyl phosphates are also briefly mentioned). As you proceed through the chapter, you should be looking for similarities in behaviour among the various classes of compounds.
- 7: Conjugated Pi Systems
- 7.1: Stability of Conjugated Dienes- Molecular Orbital Theory
- 7.2: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
- 7.3: Kinetic vs. Thermodynamic Control of Reactions
- 7.4: Naming Aromatic Compounds
- 7.5: Structure and Stability of Benzene
- 7.6: Aromaticity and the Hückel 4n + 2 Rule
- 7.7: Aromatic Ions
- 7.8: Aromatic Heterocycles - Pyridine and Pyrrole
- 8: Electrophilic Aromatic Substitutions
- 8.1: Introduction
- 8.2: Electrophilic Aromatic Substitution Reactions - Bromination
- 8.3: Other Aromatic Substitutions
- 8.4: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
- 8.5: Substituent Effects in Substituted Aromatic Rings
- 8.6: An Explanation of Substituent Effects
- 8.7: Clemmensen Reduction