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—_ PRACTICE PROBLEMS - UNIT 12 12A. Identify groups of conjugated atoms. 124.1. Determine if the alkenes in the following molecules are conjugated or isolated. a) zingiberene (in ginger) b) limonene (in citrus) c) docosahexanoicacid (in fish oll) \ealuted Cot ved ‘sclaten oe Isolreet Os Bie : (SJ ‘OH d) lycopene (in tomato) Lsaletee Condecgered, Loetes 12A.2 For the molecules below circle groups of atoms that are conjugated. a) » “Ss L OB} corny ARR) bounced b) A ; m) Comuyeled = 2 = AO Conjugated ‘OH ? n) r federed FrYAS laclaheck eg S 0) on z Vsalatet aa Ss emer d ») @ oO 1 e) . selcleck bed. Comuycted a oO TED congyeteh = AYN 4) 5 ° ° ae 2 Veeeted Aow~ \soleted n u) ©, [> leclereck ya lege Toa Longuepiens v a No Conjuples vy s) ‘i Ww Loajurpleeh vs @ As~ lolad ai - & tedeled » w) 2 2 ch (Ne tae wh oyun CI iecleved 12A.3 Although allenes have three adjacent carbons with p orbitals, they are not conjugated. Draw the P orbital system of the allene below to explain this. HC=0=cH, 68-45 124.4 Circle the molecule in each set withthe largest (most are heat of hyd ee pe ee! BO e 2 > Most eroher nw Sn Spee ay ae Ww wos exons 428. Predict the 1,2 and 1,4 products of addition of HX to symmetric and asymmetric conjugated dienes. Draw the mechanism for their formation. 12B.1 Draw the major products of the following reactions and their mechanism of formation. a ye 128.2 The reaction below produced only one product: A. Draw the intermediates that would yield each product and explain why B is not Reread oe be QP a oS a 128.3 Predict all i < products of the following reactions. By ¢ aA O23 ma “Om 8D» ) oo e) a PR ee ABP fe “gc ¢) 5 ~ An An ha Cos Ne Feecene 12C. Predict the products of the Diels-Alder reaction including stereochemistry. 12C.1 Predict the major product, if any, indicate stereochemistry where appropriate. § soa sae) 3) m) <2 gill I EX corp, @ cl ‘CO2CH3 OXf a, € pr o ” f) > ee Qy 9) woes EE me i ° .CO2CHs ..

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