There is also a way to obtain anti-Markovnikov oriented alcohols: hydroboration. Introduction 1. The boron usually ends up on the less substituted end of the olefin. #4. A) dihydroxylation using OsO4, H2O2 B) addition of H2 C) hydroboration D) addition of HCl E) A, B, and C Overall transformation : C=C to H-C-C-OH; Reagents (two steps) 1. The alkene double bond is a gateway functional group. Conversion of C–BR 2 into C–OH is stereospecific with retention of configuration. #5. BH 3 or B 2 H 6 then 2) NaOH/ H 2 O 2; Regioselectivity : Anti-Markovnikov, since the B is the electrophile. Hydroboration-Oxidation of Alkenes and Introduction to IR Spectroscopy A. Hydroboration-Oxidation of Alkenes Alkenes can be oxidized to alcohols using a two-step method of hydroboration followed by oxidation. Ch08 Reacns of Alkenes (landscape) Page 16 Hydroboration of Alkenes We have studied three ways of hydrating alkenes to give Markovnikov orientated alcohols. Stereoselectivity With Acyclic Olefins Hydroboration involves a four-membered transition state with syn-addition across the alkene/alkyne. 1 17. Draw the structural formulas for the alcohols that result from hydroboration-oxidation of the alkenes shown. The pentamethylcyclopentadienyl N‐heterocyclic carbene nickel complex [Ni(η 5 ‐C 5 Me 5)Cl(IMes)] (IMes=1,3‐dimesitylimidazol‐2‐ylidene) efficiently catalyses the anti‐Markovnikov hydroboration of alkenes with catecholborane in the presence of a catalytic amount of potassium tert‐butoxide, and joins the very exclusive club of nickel catalysts for this important transformation. Hydroboration / Oxidation of Alkenes (review of Chapter 6) Reaction type: Electrophilic Addition. A) hydroboration-oxidation B) addition of Br2 C) addition of H2 D) addition of H2O in dilute acid E) both A and B 37) Which of the following additions to alkenes occur(s) specifically in an syn fashion? Experiment 9 – Hydroboration-Oxidation of Alkenes pg. Determine the yield, micro boiling point, and record an IR spectrum of the product. Experiment 17 – Hydroboration-Oxidation of Alkenes pg. Continue the evaporation process until a constant weight of material is obtained. 5 Evaporate the ether using a stream of nitrogen and very gentle heating. The reactions of alkenes arise (E)-3-methyl-2-pentene . If you need clarification or a reminder on the nomenclature of alkenes refer to the link below on naming the alkenes. You can convert alkenes to alkyl halides, epoxides, alcohols, aldehydes, ketones, carboxylic acids, and other functional groups. Summary. Hydration of Alkenes: addition of water (H-OH) across the p-bond of an alkene to give an alcohol. Alkene reactions lead to many other functional groups that lay the foundation for the rest of your study of organic chemistry.

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