Stability of vinyl C+ is about the same as H 3 C+. NOT ASSISTED!

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1 rganic hemistry Interactive Notes hapter 8: Alkynes Naming Alkynes Structure ommon Name IUPA Acetylene ethyne methyl acetylene propyne dimethyl acetylene -butyne ethyl acetylene -butyne =- as substituent is called ethynyl. Name these: Some things to consider: The closest unsaturation to the end takes precedence: (4Z)-4-hexen--yne Double bond takes precedence if equal. Why do you think? (E)--hexen-4-yne -buten--yne eactivity of alkynes Addition reactions: slow vinyl cation The addition of to an alkyne is slower than an alkene because of two factors: the sp orbital is less basic than the sp orbital. Increased s character. the vinyl cation formed is unstable compared to an alkyl cation. ere the sp hybridized cannot be stabilized by hyperconjugation because of the pi bond perpendicular to it. - hybrid? Stability of vinyl is about the same as. NT ASSISTED!

2 rganic hemistry Interactive Notes omparison of reactivity of alkenes vs alkynes with : Alkene Alkyne E A E A General Addition of slow - st mole vinyl cation nd mole - Example: General Addition of slow trans from anti addition st mole nd mole -

3 rganic hemistry Interactive Notes Examples: Mechanism: l l l l - l l Z l l l l l l l - l l l l Addition of Water and interconversion of the (enol) vinyl alchol to a ketone. gs 4 What is the role of acid in this reaction? ow many moles of water are consumed? The enol is unstable compared to a unique rearrangement called tautomerization. The enol continues to react in the presence of acid. enol This process is called keto-enol tautomerization. What is the role of acid in this reaction? ow many moles of water are consumed? What is the definition of a tautomer?

4 rganic hemistry Interactive Notes enol ketone The substitution pattern for alkynes follows Markovinikov s rule: gs 4 & S 4 > [ = ] > -= gs 4 & S 4 > [ ()= ] > (=) ' gs 4 & S 4 >[ =()' ()='] > -(=)' (=)- ' Examples: keto-enol tautonomerism ydroboration B B B further alkylations note E orientation B keto-enol tautonomerism - (aq) 4

5 rganic hemistry Interactive Notes The complete reaction is written like this. gs 4 dilute S 4. B -TF., aq base For terminal alkynes, B -TF makes aldehydes and g catalyzed hydration makes ketones. eduction reduces alkynes to alkenes and then to alkanes. The fact that the reaction is exothermic and moreso for alkynes than alkenes, the reaction is hard to stop. The reaction takes place on the surface of Pt or Pd. Since the addition is twice, it is hard to see the syn addition. eduction of alkynes to (Z) - alkenes Lindlar s catalyst: Pd, quinoline, Pb and a poisons the metal catalyst, so that the adds only to the alkyne not reactive with alkenes. eduction of alkynes to (E) alkenes. eaction via Na radical dissolved in liquid N.

6 rganic hemistry Interactive Notes Mechanism of Na/N reductions: Na Na N (e-) - N (e-) N N N (e-) - N - N - xidation Like alkenes, either with (ozone) or KMn 4. Because of the added unsaturation of alkynes, it is hard to stop at an aldehyde. So, the reaction goes mostly to carboxylic acids. Terminal alkynes will make fizzy water. xidative conditions KMn 4.. (aq) Acid/Base What is a suitable base to make the reaction go to the right below. B:- : B For pka of B N 6 N 4 9 6

7 rganic hemistry Interactive Notes Alkylation Acetylide anion : - can react as a nucleophile and react with a 0 alkyl bromide in a substitution reaction to make a longer alkyne. This process of adding an alkyl group and is called alkylation. NaN Step : Step : MultiStep synthesis A. Prepare cis-4-octene from -pentyne Step : -pentyne to pentynyl anion Step : -pentynyl anion to 4-octyne Step : 4-octyne to (Z)-4-octene B Prepare trans--hexene from -pentyne Step : Step : Step : Working backwards: retrosynthetic strategies. B A

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