HONORS ORGANIC CHEM. HAHS MRS. RICHARDS
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1 NRS RGANIC CEM. AS MRS. RICARDS RGANIC CEMISTRY: FINAL EXAM REVIEW List of Topics: While the exam will specifically focus on material from Quarter 2, an understanding of several important concepts from Quarter 1 is also required. 1.) Naming: alkenes, alkynes, enynes, alcohols 2.) Reactions: alkenes and alkynes: determining products, reagents, reactants 3.) Mechanisms: alkenes and alkynes: electrophilic addition of X (both), halohydrin formation (alkenes only), acid-catalyzed hydration (both), hydroboration (both), acetylide anion formation/ alkylation (alkynes only) While there are no multiple choice or fill-in-the-blank questions on the exam, answering the following review questions will help assess your understanding of the concepts above and your ability to apply the information in the open-ended questions on the test. NAMING REVIEW 1. When naming an alkene or an alkyne, always find the longest chain containing the double or triple bond and start numbering this way: 2. In a cycloalkene, number the ring so that the double bond is always between and and the first substituent has as a number as possible. 3. The name of alkenes end in and alkynes end in. 4. At the end of the name, include the number indicating where the begins. 5. Enynes contain both an and an. 6. To name an enyne, find the longest chain containing both functional groups and begin numbering this way: 7. When the double and triple bonds are equidistant from the end point of a carbon chain, always give the the lowest number. 8. When naming an alcohol, find the longest chain containing the and begin numbering this way: 9. The name of alcohols ends in. 10. At the end of the alcohol s name, include the number indicating where the occurs along the carbon chain. 11. Name the following molecules (continued on next page). A B C D 1
2 NRS RGANIC CEM. AS MRS. RICARDS 11. cont d E F G I J K L M REACTINS REVIEW 12. Alkenes and alkynes both undergo electrophilic addition reactions. In this general type of reaction: a.) Describe what acts as the nucleophile. b.) What type of intermediate forms? c.) Explain how Markovnikov s Rule applies. 13. When X adds to an alkyne or alkene, describe how you know which carbon the adds to and which carbon the X adds to and why. 14. When X 2 adds to an alkene, where do the X s end up? 15. a.) When X 2 adds to an alkyne, where do the X s end up? b.) When excess X 2 adds to an alkyne, where do the X s end up and how many total add? 16. When X 2 / adds to an alkene, a halohydrin forms in which adds to the more substituted carbon and adds to the less substituted carbon. 17. Both alkenes and alkynes undergo hydration reactions. What gets added in a hydration reaction? 18. a.) To form the Markovnikov alcohol, add to an alkene. b.) To form the anti-markovnikov alcohol, add to an alkene. 19. When alkynes undergo hydration reactions, an enol forms first. a.) What is an enol? b.) What reagents are used to make the Markovnikov enol? c.) What reagents are used to make the anti-markovnikov enol? d.) What happens after the enol forms and what functional groups do the final products contain? 20. Alkenes undergo hydroxylation reactions to form diols. What reagents are used to form the diol? 21. Both alkenes and alkynes undergo oxidative cleavage reactions. a.) What are the reagents used in oxidative cleavage? b.) Describe what happens to the alkene/ alkyne bond in this type of reaction. 2
3 NRS RGANIC CEM. AS MRS. RICARDS c.) ow do the products of alkene cleavage differ from those of alkyne cleavage? d.) ow do the products of alkyne cleavage differ when the alkyne is internal vs. terminal? 22. Alkynes are typically formed via this general type of reaction:. a.) Vinylic halides react with to form alkynes. b.) 1,2-dihalides react with to form alkynes. 23. Alkynes undergo reduction reactions which result in an increase in this type of bond: a.) Complete reduction occurs when the alkyne reacts with to form an. b.) Incomplete reduction occurs when the alkyne reacts with to form a cis alkene or with to form a trans alkene. 24. Terminal alkynes are weakly acidic; they react with to form this type of anion: 25. When an alkylation reaction occurs, the acetylide anion reacts with a to form a new bond. 26. Draw the product of each reaction. a.) 2. 2 / - h.) 3 Zn, 3 + b.) 2 i.) NaN c.) 2 j.) 1. s 4 d.) 2 k.) 2. NaS 3 e.) Li N 3 l.) 2 excess f.) 2. 2 / - m.) 3 Zn, 3 + g.) n.) K S 4 3
4 NRS RGANIC CEM. AS MRS. RICARDS 26. cont d o.) t.) excess p.) 3 + u.) 2 r.) v.) 3 Zn, 3 + s.) Pd / C w) 1. NaN 2. C 3 C x.) Lindlar 27. Identify the reagents needed to perform each reaction as shown. a.) h.) + C 2 b.) i.) c.) j.) d.) k.) e.) l.) f.) m.) g.) n.) 4
5 NRS RGANIC CEM. AS MRS. RICARDS 27. cont d o.) r.) p.) s.) q.) t.) MECANISMS REVIEW 28. When drawing a reaction mechanism, the arrow always begins where the electrons and points to where the electrons. 29. We have seen two types of reaction mechanisms that do not occur through carbocation intermediates. What are they? (*We have seen several reactions that do not occur through carbocations; this question is specifically about reactions for which we have seen mechanisms.) 30. Draw the mechanism for each reaction shown below. Be sure to clearly show arrows as well as any bonds that break/ form and any + / charges that form. A.) E.) 2. 2 / - B.) S 4 F.) C.) 2 G.) 1. NaN 2. C 3 C D.) 2. 2 / -.) S 4 5
When H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group:
Next Up: Addition of, : The next two reactions are the Markovnikov and non-markovnikov additions of and to an alkyne But you will not see alcohols form in this reaction! When and add to the alkyne, an
More informationsp 2 geometry tetrahedral trigonal planar linear ΔH C-C ΔH C-H % s character pk a 464 KJ/mol 33% 44
hapter 10: Alkynes 10.1 Introduction to Alkynes ~ 111 ~ 122 1.06 Å 180 1.1 Å ~ 116 1.08 Å 1.54 Å 1.34 Å 1.20 Å hybridization of sp 3 sp 2 sp geometry tetrahedral trigonal planar linear 368 KJ/mol 632 KJ/mol
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