The following reaction follows a free radical mechanism. Write the mechanism for the reaction showing how the two products are formed. Include the initiation and termination steps and important intermediates. Br₂, hv (light) H Br + HBr
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- CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below. CH3 OG 1 Use wedge and hash bonds ONLY for rings. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. ● 981 CH3 ***** // Q Y ? [F BDuring multistep syntheses, reduction reactions are often performed. Functional groups react differently with these reagents. With this in mind, draw the structure of the product of this reaction: CO₂H CO₂H s HO₂C • For your convenience, the starting material has been drawn for you in the sketchpad. HO OH LIAIH4 -OH - [ ] ?
- H₂C- The following road map explores the reactivity of alkynes. Supply the missing reagents over the arrow and the missing products after the arrow. ECH A H₂C H₂C Na CH₂I CH3 1 Br₂ E B D H₂(g). Lindlar's catalyst 1. BH₂-THF 2. NaOH(aq). H₂O₂ F4) Fill in the appropriate starting materials, reagents or products in the following reactions. OH / AIC13 NO₂ Y CI / AICI,What carboxylic acid would you reduce to produce the following alcohol? H3C с. H3C CH3 . You do not have to consider stereochemistry. **** C P opy aste OH Y []* ChemDoodle
- A common alkene starting material is shown below. Predict the major product for each reaction. Ignore any inorganic byproducts. I I Select to Select to Draw I Draw I HBr Cl₂ H₂O 1. BH3-THF 2. H2O2, NaOH nd 1.03 2. (CH3)2S36. Which of the following is a tertiary alkyl halide? A. (CH) CHBr B. (CH) CHCH.C C. (CHICCI D. CH.CHICHI E. CH.CHB 37. What is the product? CM₂ CH₂CH-CH(CH₂CH₂OH CH, A H,CH₂CCHICH OCH₂ AA B.B C.C substitution only CH₂ B (H₂CMC-CHICH, OCH C. both A and B9 Name these compounds. NO₂ (a) Clon (e) (g) Br (c) C₂H₂CH₂CH₂CH₂Cl (d) C.H.CCH₂CH3 bi | CH3 384 Chapter 12 Alkenes, Alkynes, and Aromatic Compounds NH₂ OH C6H5 arres NO2 H C=C / (b) H C6H5 (f) (h) CH3 CH3 Br Cl C6H5 Cl byd T
- Which of the following reactions form the product shown. N2OH H,O H20 1.(CH3COH, Hg(o.CCF2 CH2 2. NABH4 HBr Br CH; CH-CH3 HO H3C,ACH: CH: CH CH3 H3C OHDraw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2O1. Assign E or Z to the following alkenes. If the alkene does not have stereochemistry, write "NONE". H CI H3C SH T. H CI, ОН H3CH2C НО D D EN C(CH3)3 CH3 Me H Et N' 'N' C=C H3C Et Me what Columbus sought in the 'Indies' - Piperine CH2OH Br (H3C);C, H3C HOH, CH,CF, H3C Br HOH2C НО H the spice Columbus found (Capsaicin) HO. Muscalure Bombykol (the sex attaractant for the male silkworm) (the sex attaractant for the common housefly) OH .CO2H the "heart healthy" part of olive oil a 'less healthy' trans fatty acid from trans fat