tb6 - Chaoter 6 - Alkenes: Structure and Reactivitv...

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Chaoter 6 - Alkenes: Structure and Reactivitv Calculate the degree of unsaturation in each fonnula below. Show your calculations. 1. pinene, ClOHl8 Answer: The saturated ten carbon compound would have 22 hydrogens so the number of degrees of unsaturation is: (22 -18) -;-2 = 4 -;-2 = 2 . 2. eicosapentaenoic acid, C2oH3002, a constituent offish oil Answer: Oxygen does not affect the base fonnula which in this case is C2oH3o. The saturated'20 carbon compound would have 42 hydrogens so the number of degrees ofunsaturation for eiscosapentaenoic acid is: (42 - 30) -;-2 = 12 -;-2 = 6. 3. diazepam (Valium), C16H13N2OCl Answer: Oxygen does not affect the base fonnula. A hydrogen is added to the base fonnula for each halogen and subtracted for each nitrogen so the base fonnula for diazepam is C16H12' The saturated 16 carbon compound would have 34 hydrogens so the number of degrees of unsaturation for diazepam is: (34 - 12) -;-2 = 22 -;-2 = 11. Dieldrin, C12HgCI6O, is a pentacyc1ic compound fonnerly used as an insecticide. 4. Calculate the degree ofunsaturation for Dieldrin. Show calculations for credit. Answer: Oxygen does not affect the base fonnula. A hydrogen is added to the base fonnula for each halogen so the base fonnula for dieldrin is C12H14. The saturated 12 carbon compound would have 26hydrogenssothe numberof degreesof unsaturationfor dieldrinis (26 - 14) -;-2 = 12 -;- 2=6. 5. How many double bonds does dieldrin have? Answer: Dieldrin has 6 degrees of unsaturation and it is pentacyc1ic, meaning it has 5 rings. Therefore, dieldrin must have one double bond. Draw structures corresponding to each name below. Either condensed or line structures may be used. 6. (3E)-3, 7-dimethyl-l ,3,6-octatriene Answer: ~ or (CH3hC= CHCH2 CH3 \ / C=C / \ H CH= CH2 Test Items for McMurry's Organic Chemistry, Seventh Edition 37
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7. 3,6-dimethyl-l,4-cyclohexadiene CH3 Answer: CH3 8. cis-2-hexene Answer: ~ 9. trans-4,4-dimethyl-2-pentene Answer: ~ or or or H3C CH2CH2CH3 \ / C=C / \ H H H3C H \ / C=C / \ H C(CH3hCH3 2-Pentene is an example of a disubstituted alkene.
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tb6 - Chaoter 6 - Alkenes: Structure and Reactivitv...

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