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- https://chem.libretexts.org/Courses/Martin_Luther_College/Organic_Chemistry_-_MLC/03%3A_Alcohols_Ethers_Thiols_Sulfides_and_Amines/3.01%3A_Alcohols_and_Phenols/3.1.07%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/17.06%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/Workbench/Community_College_of_Baltimore_County_Organic_Chemistry_1/11%3A_Alcohols_and_Phenols/11.07%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/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/17%3A_Alcohols_and_Phenols/17.07%3A_Reactions_of_AlcoholsThe S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with t...The S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with the same stereochemistry as the starting alcohol.
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/03%3A_Alcohols_and_Ethers/3.07%3A_Reactions_of_AlcoholsThe S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with t...The S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with the same stereochemistry as the starting alcohol.
- https://chem.libretexts.org/Workbench/Chemistry_LHS_Bridge/15%3A_Alcohols_and_Phenols/15.07%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/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/17%3A_Alcohols_and_Phenols/17.07%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/Courses/can/CHEM_231%3A_Organic_Chemistry_I_Textbook/12%3A_Alcohols_and_Phenols/12.06%3A_Reactions_of_AlcoholsThe S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with t...The S N 2 reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration—one to make the halide from the alcohol and one to substitute the halide—and yields a product with the same stereochemistry as the starting alcohol.
- https://chem.libretexts.org/Courses/Smith_College/CHM_222_Chemistry_II%3A_Organic_Chemistry_(2025)/09%3A_Alcohols_and_Phenols/9.07%3A_Reactions_of_Alcohols_(CHM_223)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 ...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_(OpenStax)/17%3A_Alcohols_and_Phenols/17.06%3A_Reactions_of_AlcoholsWe’ve already seen several reactions of alcohols—their conversion into alkyl halides and tosylates in Section 10.5 and their dehydration to give alkenes in Section 8.1—albeit without mechanistic detai...We’ve already seen several reactions of alcohols—their conversion into alkyl halides and tosylates in Section 10.5 and their dehydration to give alkenes in Section 8.1—albeit without mechanistic details.
