MECHANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). >Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s).
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Epoxides shows SN1 type ring opening reactions when treated in acidic medium whereas they shows SN1 type in basic medium.
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- Q17. Compound 1 can undergo an intramolecular reaction to give cyclic product 2. Using curly arrows, show the mechanism of this reaction – note that the mechanism involves more than one elemental step - and draw the structure of 2; chemical formula is provided as guidance. H,N. CsHgNO + CH;OH 2Q3. Consider the following reaction. Give the structure of the most likely carbon-containing product and justify your answer with a detailed curved-arrow mechanism. NaOEI, HOE! H₂ON(CH2CH3)3 + HNO3 --------> a.) rewrite the reaction using bond-line structure of reagents and products of the reaction b.) supply the curved arrows explaining the mechanism of the reaction
- 4. Synthesis Using the carbon-containing starting material(s), propose a synthesis by drawing structures for all intermediates. The carbon atoms in the product must originate from the starting material(s) (or a carbene/carbenoid or CO₂), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know. (note: no mechanisms are required). (a) || محمد bAlkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two O Hint in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. The first step of the reaction, hydroboration, involves addition of BH, to the double bond, with -BH, attached to one carbon and hydrogen Be sure to draw hydrogens on oxygen, where applicable. attached to the other. Consider both Rings the regioselectivity and the Select Draw More Erase stereochemistry of this addition. H Diborane, B,H,, is a source of borane, BH,, and can be used 1. B2H6, interchangeably. Diglyme is a solvent. diglyme 2. H2О2, НО", The product or products of the reaction are characterized as being O S. O racemic. O achiral. O R,S (and/or S,R). O R. O S,S. O R.R. O diastereomers.How is the mechanism for oxymercuration/demercuration reactions of alkenes understood? How are the (Markovnikov) products predicted and what reagents would you need to use to incorporate this reaction into a multistep synthesis strategy. Finally, what makes this a potentially more useful way to synthesize alcohols from alkenes than simple acid hydration?
- Chemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH Cold(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H20 Compound X 100 - MS-IW-5644 80 60 40 - 20 - 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X: Br Br HO, IV V I II II Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity1. Draw the structures of the following substituents and place them in descending order of priority. (a) Methyl, bromomethyl, trichloromethyl, ethyl; (b) 2-methyl-propyl (isobutyl), 1-methyl-ethyl (isopropyl),cyclohexyl; (c) butyl, 1-methyl-propyl (sec-butyl), 2-methyl-propyl (isobutyl), 1,1-dimethyl-ethyl (tert-butyl); (d) ethyl, 1-chloro-ethyl, 1-bromo-ethyl, 2-bromo-ethyl. 2. Check the absolute configuration of the items below: a) b) d) H "CH₂CH3 CH3 Br CH3 f F |||| H₂N- CH₂CH3 CH3 fr -COH H f) HC H- H Br HC. "ICH3 FCH₂ CH3 CH3 Br H
- Review Tepics) Raterences In cach case below select the synthetic procedure's that could be used to carry out the transformation, giving the alcohol shown as the single major product. The procedures are: Hydroboration/oxidation: alkene + BHy, then H,O, OH. Oxymercuration: alkene + Hg(OAc), H,O; then NaBH, treq CH, CH,CH,CHCH=CH, CH3 CH,CH,CHCHCH, hydroboration/oxidation OH CH,CH,CHCH;CH,CH, CH,CH2 H. hydroboration/oxidation An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer Submit Answer Retry Entire Group 2 more group attempts remainingQ17. Compound 1 can undergo an intramolecular reaction to give cyclic product 2. Using curly arrows, show the mechanism of this reaction – note that the mechanism involves more than one elemental step - and draw the structure of 2; chemical formula is provided as guidance. H2N. C5H9NO CH3OH 2Identify the major product of the reaction of an alkene shown below. ||| 1. Hg(OAc)2, H2O 2. NaBH4, NaOH ....... ОН || IV ОН о, ОН