TAILIEUCHUNG - Lecture Organic chemistry - Chapter 13: Alkynes: The C≡C Triple bond

Lecture Organic chemistry - Chapter 13: Alkynes: The C≡C Triple bond. This chapter presents the following content: Introduction to alkynes, natural occurrence and uses of alkynes, physical properties of alkynes, spectroscopy of alkynes, nomenclature of alkynes, acid-base properties of alkynes,. | Like alkenes, but ending -ene turns into –yne. HC CH Ethyne 5 4 3 2 1 1-Pentyne Br 1 2 3 4 5 6 5-Bromo-2-hexyne -ol -yne > OH 1 2 3 2-Propyn-1-ol Chapter 13: Alkynes: The C C Triple Bond Naming Priority: When the alkyne contains also double bonds, it is called an enyne. However, despite being an “yne”, numbering begins closest to either group: 1 2 3 4 5 6 3-Hexen-1-yne 1-Penten-4-yne When double and triple bond are equidistant from each terminus: ene first (alphabetical) 1 2 3 4 5 6 7 1-Hepten-4-yne 1 2 3 4 5 Substituents: Ethynyl 2-Propynyl (or propargyl) Smaller R is a substituent to larger R 3-Cyclobutyl-1-hexyne Ethynylcyclohexane but 1 2 2-Propenyl (or allyl) 1 2 Remember: Two perpendicular π bonds; sp hybrids R C C R Ethyne Structure The Triple Bond Is Energetic Heat of hydrogenation: more than two alkene bonds (which would be ~ -60 kcal mol-1) Acetylene torch: ~3,500 C Internal triple bond is more stable : : RC C H + B R C C + HB Hydrogens get more acidic (blue) - - pKa ~ .

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