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tb5 - Chaoter 5 4n Overview of(Jrllanic]J.eactions ClassifY...

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Chaoter 5 - 4n Overview of (Jrllanic ]J.eactions ClassifY each reaction below as a(n): a. addition b. elimination c. substitution d. rearrangement Place the letter corresponding to the correct answer in the blank to the left of the reaction. 1. 0 Clz :: I catalyst- (r CI I + ~ HCl Answer: c 2'-d' acid - catalyst cf Answer: d 3'-0 Br2 - 6...& Answer: a IdentifY the functional groups present in each compound below and predict the direction of polarity in each. 4. mustard gas CI - CHzCHz - S - CHzCHz - CI Answer: Halide Sulfide Halide Test Items for McMurry's Organic Chemistry, Seventh Edition 27
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amphetamine NHz I affi2ffiffi3 5. Answer: ~ - ~ aromatiC ring b:z 3 ~ 0+ ~ I amme Classify each structure below as a nucleophile or electrophile and briefly explain your choice. .. 6. azide :N=N=N: + Answer: Azide is a nucleophile since it has a net n'egative charge (and lots of electron pairs!). H I. 7. hydronium ion O' H"+'H Answer: Hydronium ion is an electrophile since it has a positive charge. 8. phenol ~.. ~O-H Answer: Phenol can be a nucleophile or an electrophile ~OPhili~ 0- 0- 0+ O-H ~ /; .. ~OPhilic Identify the nuclephile and electrophile in each reaction below and label them. 9. ()~. + H-Cl - 0.0~H + cr - 28 Chapter 5: An Overview of Organic Reactions
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Answer: " cr~' + H-Cl - ()'O~H + cr - nucleophile electrophile cr~' + u- :0: 10. - - (j-CN :C N: - Answer: croqo + .. - :0: - - (j-CN :C- N: - electrophile nucleophile 11. .. H-O-H + H3C- MgBr .. Answer: u H-O-H + H3C- MgBr .. electrophile nucleophile 12. croq. + ()'O~H H-Cl - + cr - Answer: -0. ()OO~H cr~cJ - + cr - ~ + ;; + H9.: MgBr . ~ + ;; + HO: MgBr . Add curved arrows to the following reactions to indicate the flow of electrons in each. Test Items for McMurry's Organic Chemistry, Seventh Edition 29
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-'~,,",",,-"Y~~'-'<.<"'- .0. 13. 0' + :C=N: - u- d:~ - Answer: ~.b. ~:C=N: - .. - :0: ()-~ - 14. H-O-H u + H3C- MgBr ~ ~ + eo + HO: MgBr u Answer: H-~ ~-Mg!k ~ ~ + ;; + HO: MgBr u 15. Acidic ether cleavages are typical substitution reactions. Use the information in Table 5.3 ofthe textbook to calculate Mfo for the reaction of ethyl methyl ether with hydrogen chloride and hydrogen iodide.
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