For each of the following pairs of Sy2 reactions, indicate which reaction occurs faster: a) CH,CH,Br + H,0 OR CH,CH,Br + OH b) Remember the following is under an S,2 condition: CH,CHCH,Br CH3 OH CH3CH2CHBR + OH OR
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- Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:Organic Chemistry: Alkyl halides only 1. For each of the following pairs of S2 reactions, indicate which reaction occurs faster: a) CH:CH2BR + H20 OR CH:CH,Br + OH b) Remember the following is under an SN2 condition: CH,CH2CHBR + OH CH,CHCH,Br ČH3 OH OR 2. What is the product of the reaction of ethyl bromide with each of the following nucleophiles? a) CH;CH;CH2O b) CH;C=C c) (CHa)aN 3. Arrange the following alky halides in order of decreasing reactivity in an SN1 reaction: a) 2-bromopentane, 2-chloropentane, 1-chloropentane, 3-bromo-3-methylpentane2) Write the major products A- P for each of the following reactions. d) H,O/ H* concd. H,SO4 Br/ CCl, excess NaNH2 K M heat NH3
- Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use? O KOH/H2O O KOH/CH,OH O CH3CH2ONA/CH3CH2OH O CH3ONA/CH3OH O (CH3)3COK/(CH3)3COHConsider the following overall reaction, which will be discussed in Chapter 20. H,C-CEN NH3 HOO H,C Below is a proposed mechanism for this reaction. Use the rules we learned in this chapter to evaluate whether each step in the proposed mechanism is reasonable. For each step that is not reasonable, explain why. :ÖH () H,C-CEN: H3C OH OH (i) + H,C H3C OH OH (ii) H,C H,C OH (iv) + H,O: H,C H,C OH (v) H3C H3C OH H. (vi) :NH, NH. H,C H,COne of the steps in the mechanism of the above reaction as shown below. Draw the structure of all the products of this reaction. com/mm/takeAssignCourt Rotivity.do?locator assignment-take 1 pt ment Eto O Eto O 3. NaOH, H₂O, heat 4. HCI, H₂O, heat One of the steps in the mechanism of the above reaction is shown below. Draw the structure of all of the products of this reaction. O OEt O 1. Eto Na 2 Å OH You do not have to consider stereochemistry. • Draw enolate anions in their carbanion form. . You should include all products. Ôno P Ć [References) . Include counter-ions, e.g., Na, I, in your submission, but draw them in their own separate sketcher. . Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. . Separate multiple products using the + sign from the drop-down menu. ///-000- IF Previous Email Instructor
- 6) Fix the reaction: The following reactions will not work as shown. Explain why the reaction will not work and create a reaction that will work. (Change only reagents. Leave starting material and product CH, H,C CH, Br. hv H,O/H,0 CH HO HO но 1) NANH, 2)CH,Br H3C = HC= CH3 HBr H3C. Br CH3 он CH2 1)MСРВА X, 2) HCI CIQ6. Predict the structures of the final products of the following transformations. 1. NaNH, NH, CI 2, L, NH Q7. Identify the products of the following sequence of reactions. for Br KOH, CH₂CH₂OH BH₂/H₂O/H₂O₂, OH4. Give the IUPAC name of the alkyl halides involved in each of the reactions below. Tell whether the following reactions is likely to be SN1, SN2, E1, E1CB, or E2. Choose 1 item and show its mechanism. NaN3 Br THF a. кон Ethanol CI CH;COOH CH3 -CI OH NaOH Ethanol
- 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 HO5. Predict the MAJOR product and provide the mechanism for the following reaction. Make sure to include the formation of the electrophile and any relevant resonance structures (of the electrophile AND substrate). Note: do not use water in any step in this mechanism. HC- CI ои G,Ou затв MS сиз- - но, 2n₂ CI و -Alely -> د۔ > 54 CI AIC13 CH₂- c-ens CHO cus دے CH3 = د Alcs C=O @o 0 er acylimien OH ON сосну CUO C4₂ (minor (major)Provide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IV