Quiz_I_Key_su09 - ID<€y Chem 308 Summer2009 NAME Quiz1...

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Unformatted text preview: ID \<€y . Chem 308, Summer2009 NAME - Quiz1 Section V1 1. (3 pts.) Draw the structures of the two major products of the reaction below. Ignore stereochemistry. - NBS, hv CH2 2. (3 pts.) Draw a p-orbital representation (use shading or +/— to indicate orbital phase) of the highest—energy occupied. molecular orbital (HOMO) of 1,3,5-hexatriene. The bonding orbital of an allyl system is shown as an example of the style you should use. , ANSWER: . (HOMO of 1,8,5—hexatriene) Example . l ‘ 3. (3 pts.) Draw the most important additional resonance structures of the carbocation shown below. Number each structure according to its relative importance (1 = most important, 3 2 least important). _ 293R tor Me) «—-—-> k/\// 4'3"} %\/\// Stiff x. l ' § 1 \ Pfimkrzfl . 4. (3 pts.) Write a detailed mechanism for the reaction shown below, showing all intermediate structures. Use curved arrows to indicate all electron movement, and indicate all formal charges clearly. CH30H ' . Ml . M ~ lot {Jar missing} (ix-emf or" arrow l<L é Y ID Chem 308, Summer 2009 NAME: Quiz1 Section V2 1. (3 pts.) Draw the structures of the two major substitution products of the reaction below. ignore stereochemistry. \jk V r ' V\ + gr/\%\: V K\ qt ‘3; WW Gal. LN]: filmk‘ivé) 2. (3 pts.) Draw a p-orbital representation (use shading or +I— to indicate orbital phase) of the lowest—energy unoccupied molecular orbital (LUMO) of 1,3—butadiene. The bonding orbital of an allyl system is shown as an example of the style you should use. ANSWER; , . i with (LUMO of 1,3—butadiene) 3. ' (3 pts.) Give the reagents needed for the synthetic transformation shown below.~ Use numbers to indicate the conditions for each sepaiate regacti‘ori: Tr? 6’7 9g“; 10. Nag Am) 3 a «A, V) \ \. X‘b mac {T¥\q: g I <\ ' OH ' V \ unfit? ‘ Q; ifimfiow‘m \/>< a 7 3, it» (Maxims) 4. (3 pts.) Write a detailed mechanism for the reaction shown below, showing all intermediate structures. Use ' curved arrows to indicate all electron movement, and indicate all formal charges clearly. ,I ”am HfBr ' //\/0\/ . wBr + HO\/ ...
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