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- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/17%3A_Alcohols_and_Phenols/17.02%3A_Naming_Alcohols_and_PhenolsAlcohols can be classified as primary (1 o ), secondary (2 o ), or tertiary (3 o ) depending on the number of alkyl substituents attached to the carbon bonded to the O-H group. As discussed in Section...Alcohols can be classified as primary (1 o ), secondary (2 o ), or tertiary (3 o ) depending on the number of alkyl substituents attached to the carbon bonded to the O-H group. As discussed in Section 3-3, the common system names alcohols as if the hydroxyl group (-OH) is attached to a single substituent with the word alcohol added at the end (Name of the substituent + Alcohol).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/17%3A_Alcohols_and_Phenols/17.06%3A_Reactions_of_AlcoholsNotice that unlike the halogenation reactions above, the C-O bond of the alcohol is not broken during the conversion to a tosylate or mesylate so the reaction proceeds with retention of configuration ...Notice that unlike the halogenation reactions above, the C-O bond of the alcohol is not broken during the conversion to a tosylate or mesylate so the reaction proceeds with retention of configuration at the electrophilic carbon. Notice in the mechanism below that the alkene formed depends on which adjacent proton is abstracted: the red arrows show formation of the more substituted 2-butene, while the blue arrows show formation of the less substituted 1-butene.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/17%3A_Alcohols_and_Phenols/17.07%3A_Oxidation_of_AlcoholsSecondly, a proton on the (now positive) OH is transferred to one of the oxygens of the chromium, possibly through the intermediacy of the pyridinium salt. The next step is a concerted E2-like reactio...Secondly, a proton on the (now positive) OH is transferred to one of the oxygens of the chromium, possibly through the intermediacy of the pyridinium salt. The next step is a concerted E2-like reaction where a hydrogen is removed from the alcohol, the C=O bond is formed, an acetate group is eliminated from the iodine atom, and the iodine (V) atom gains two electrons to be reduced to iodine (III).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/15%3A_Benzene_and_Aromaticity/15.02%3A_Structure_and_Stability_of_BenzeneThe six-membered ring in benzene is a perfect hexagon with all carbon-carbon bonds having an identical length of 139 pm 1 . The 139 pm bond length is roughly in between those of a C=C double bond (134...The six-membered ring in benzene is a perfect hexagon with all carbon-carbon bonds having an identical length of 139 pm 1 . The 139 pm bond length is roughly in between those of a C=C double bond (134 pm) and a C-C single (154 pm) which agrees with the benzene ring being a resonance hybrid made up of 1.5 C-C bonds.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/15%3A_Benzene_and_Aromaticity/15.05%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Workbench/Chemistry_LHS_Bridge/15%3A_Alcohols_and_Phenols/15.05%3A_Alcohols_from_Carbonyl_Compounds-_ReductionIn organic chemistry, it is often more convenient to regard reduction as the gain of hydrogen or loss of oxygen, and oxidation as the gain of oxygen or the loss of hydrogen. For example, when hydrogen...In organic chemistry, it is often more convenient to regard reduction as the gain of hydrogen or loss of oxygen, and oxidation as the gain of oxygen or the loss of hydrogen. For example, when hydrogen is added across the double bond of ethene to reduce it to ethane, the oxidation number of the doubly bonded carbon atoms decreases from −II to −III. During the reduction the C=O double bond in the reactant and forms a C-O single bond in the product.
- https://chem.libretexts.org/Courses/Alma_College/Organic_Chemistry_I_(Alma_College)/02%3A_Conjugation_Resonance_and_Aromaticity/2.09%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/03%3A_Chemistry_of_Benzene_-_Reactions_of_Aromatic_Compounds/3.11%3A_Synthesis_of_Polysubstituted_BenzenesThe ability to plan a successful multi step synthesis of complex molecules is one of the goals of organic chemists. It requires a working knowledge of the uses and limitations of many organic reaction...The ability to plan a successful multi step synthesis of complex molecules is one of the goals of organic chemists. It requires a working knowledge of the uses and limitations of many organic reactions - not only which reactions to use, but when. A few examples follow:
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/10%3A_Benzene_and_Aromaticity/10.03%3A_Structure_and_Stability_of_BenzeneThe six-membered ring in benzene is a perfect hexagon with all carbon-carbon bonds having an identical length of 139 pm 1 . The 139 pm bond length is roughly in between those of a C=C double bond (134...The six-membered ring in benzene is a perfect hexagon with all carbon-carbon bonds having an identical length of 139 pm 1 . The 139 pm bond length is roughly in between those of a C=C double bond (134 pm) and a C-C single (154 pm) which agrees with the benzene ring being a resonance hybrid made up of 1.5 C-C bonds.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/15%3A_Benzene_and_Aromaticity/15.06%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/15%3A_Benzene_and_Aromaticity/15.04%3A_Aromaticity_and_the_Huckel_4n__2_RuleIn 1931, German chemist and physicist Erich Hückel proposed a theory to help determine if a planar ring molecule would have aromatic properties. His rule states that if a cyclic, planar molecule has 4...In 1931, German chemist and physicist Erich Hückel proposed a theory to help determine if a planar ring molecule would have aromatic properties. His rule states that if a cyclic, planar molecule has 4n+2 π electrons, it is considered aromatic. This rule would come to be known as Hückel's Rule.
