b Draw curved arrows to show the rearrangement of electrons in the second step leading to the 1-butene byproduct. Arrow-pushing Instructions H3C HHHH HHI H3C H H B: H BH
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- 20. Identify the product for each step in the following reaction sequence. Write complete equations showing the structure of all reactants and products for each step. (a) Isopropyl benzene + NBS/heat ---------->A (b) A+ t-BuOK ---------> B (c) B + 1)BH3 followed by 2)H2O2/NaOH -----> C (d) C + PCC ------> Db) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OHCH;O In the substitution reaction: (S)-2-bromononane CH;OH The product(s) of the reaction is(are)? OCH, OCH3 OCH3 A mixture of the major product c with the minor product d A equimolar mixture of b and c.
- OH H₂SO4 HỌC–CH2–CH2CH3 H,C=CH—CH,—CH3 + H₂O Acid-catalyzed dehydration of 1-butanol yields 1-butene as the major product. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions H2C=CH=CH2CH3 NOC XT + OH₂ HỌC–CH—CH, CH3 I H H-O-HMECHANISM ACTIVITY Base-Induced Ester Hydrolysis (Saponification) NOC XT Step 1: Nucleophilic addition of hydroxide ion to the ester carbonyl group Ahrs MPR R16 H3C. R Part A (1 of 2) Draw the curved arrows for Step 1 of this mechanism. Arrow-pushing Instructions CH3 H-O: ÖH OR' :Ö H-O: O: H H H H 1x xxx CH3 CH3 Step 1 H3C. CH3 за4. Give the starting alkene and any other reagents needed to selectively make the following compounds (with no organic byproducts!): OH L Eto OH all OH Br Br Br
- 3. For questions "A"- "C", complete the following reaction schemes (no mechanisms required). Show all reagents used in the order of application. th A) 6 B) ||| Ins HO HOc) Predict the product of the first and third steps and propose a mechanism for all three steps. Br2 NaH CH;OH H20 + EN H*3. Show the mechanism for the acid catalyzed addition of H2O to the following ketone. OH H20 CH3 H* 4. The scheme below shows the reaction of a ketone, 2-propanone with methanol. OH :0 : || CH,-C-CH3 : ОН + H CH, c-CH3 CH;-C-CH3 N step 1 step 2 step 3 P CH,OH CH3 CH,OH step 4 + H OCH3 CH,-C-CH3 H - H,0 C-CH3 ÓCH, S CH; step 7 step 6 step 5 OCH3 i) Write the missing structures (N, O, Q and R) in the above reaction scheme. ii) Name the class of compounds P and S belong to? iii) This is an acid catalyzed reaction. What does this statement mean? iv) Draw the arrow diagram in step 6 to show how intermediate R is formed? Write the equation for this step ONLY. v) Steps 3 and 7 involve loss of a proton from the intermediate ions. Why is this step necessary?
- Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? но OH но он || II IVBr CH2 HBr CH3 Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions CH2 Н— Br:Show steps and reagents necessary to obtain the following products in reactions. (Ex: process could be addition of bromine, hydrogenation, hydroboration, addition of HOX, elimination reactions, oxymercuration/demurcuration, etc) 4) Br H H. Br 5) H. H H 6) он