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OMET Practice Problem Answer Key

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311 views11 pages

OMET Practice Problem Answer Key

answer

Uploaded by

Gieanne Aregor
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CHEM 344 Organometallic Chemistry Practice Problem Set (not for credit) Summer 2013 Name (print): ANSWER KEY |) The strength of the C-X bond of halobenzenes Ph-X was explored via computational chemistry in Chapter 5, a) Explain the experimental bond dissociation enthalpy values shown below. —_ Phx | ie 127 Cl Cr) Br Cc 4 | | | 67 Larger AH® value = stronger C-X bond. With the increasing bond strength, the C-X bond distance will decrease. Stronger bond = shorter bond. b) Briefly explain which of the above halobenzenes is the least reactive toward the oxidative addition of a metal such as Mg or Pd, Fluorobenzene is the least reactive because the C-F bond is the strongest of the series and thus the oxidative addition step is most difficult. 2) Show all products of the following transmetallation reactions. The electronegativity values for each element shown in the handout may be useful (think about the nature of the C-M bond in the product(s)) 2Buli+ Cul ———2 Bu, Culi + Lil Seger + BusSnBr ——p> Sgn pu, + MgBrp on ae AR SnBus — o~* + BusSnl Me Q 2 ine ce ae LL > + MgBrCl CiMg’ 0 Pd ° Me ro re °. PdBr Il °. Pd OMe + —> Meo” B(OH), Cw 3) Suzuki-Miyaura coupling reactions typically occur between aryl or alkenyl halides and an arylboronic acid. An example of such a reaction is shown below for the synthesis of the food flavoring compound trans-anethole (trans-|-methoxy-4-(-propenyl)benzene). Pd(PPh3)4 B(OH), cy + \Aa, “St Meo’ H,O/THE MeO 4-methoxyphenylboronic acid trans-anethole a) Propose a synthesis of 4-methoxyphenylboronic acid starting from phenol, Recall that trimethylborate, B(OMe),, reacts as an electrophile toward Grignard reagents. Show all isolated intermediates/products formed. You do not need to give a mechanism for the individual steps. NaOH 0 oo HO’ isola MeO” | Mg, EO B(OH), 1) DAOMe), MgBr or “DOM 1,0 Meo”

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