Hbr to epoxide

1. The IUPAC name of the following epoxide is: H3C H H CH2CH3 O 1) cis-2-ethyl-3-methyloxirane 2) trans-2-ethyl-3-methyloxirane 3) trans-1ethyl-2-methyloxycyclopropane 4) trans-1-ethyl-2-methylethane epoxide 2. Consider the three compounds below. A. CH3CH2OCH2CH3 B. CH3CH2CH2CH2CH3 C. CH3CH2CH2CH2OH

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When acid is added to epoxides, nucleophiles will add to the more substitution position. The stereochemistry of this addition is trans. Epoxide opening [acidic conditions] Explained: Epoxides can open three-membered ring and this can be achieved with base or acid. As an acid can be used hydrogen halide acid (HCl, HBr, HI).

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HBr H H + Br r Protonate Cation Capture H o Protonate first o Capture cation second o Cation formaton (step 1) is the slow step Rank the Reactivity of the following toward HBr addition. 3 (2º) 2 (3º) 1 (3º allylic) Issue: Cation stability Why Does Markovnikov’s Rule Apply? Product/Stability Reactivity Rule.

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Hbr to epoxide

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(A) 1 is the trans-epoxide and 2 is the (B) 1 is the trans-epoxide and 2 is the meso-1,2-diol racemic 1,2-diol (C) 1 is the cis-epoxide (D) 1 is the cis-epoxide (E) None of these and 2 is the meso- and 2 is the racemic 1,2-diol 1,2-diol 16. Which set of reagents would be best to synthesize the compound shown below from cyclopentene?
(2/94)(5-8/96)(7,8/01)(1,2/02)(10-12/03) Neuman Chapter 9 3 9: Formation of Alkenes and Alkynes. Elimination Reactions •Elimination Reactions •Mechanistic ...

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2 HBr Heat (ethers) Cleave the bond on each side of the O. Each piece seperates and adds Br in place of O. (if pi-bond next to O-C bond, do NOT cleave. H2SO4 Heat (epoxides) NaOCH3 CH3OH (epoxides) opens epoxide on less sub side. adds -OCH3 and -OH anti-addition: H2O2 25c (thiols) sulfide --> sulfoxide (one double bonded O to S) NaIO4 25c

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