Chem 308_Summer 2010_Quiz 1 and 2 keys

Chem 308_Summer 2010_Quiz 1 and 2 keys - Y . ID Chem 308,...

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Unformatted text preview: Y . ID Chem 308, Summer 2010 NAME r Quiz 1 Section ‘H3 1. (2 pts.) Draw the structure(s) of the major organic product(s) of the reaction below. Br m 2. (2 pts.) Draw a p—orbiial representation (use shading or +l~ to indicate orbital phase) of the highest-energy occupied molecular orbital (HOMO) of 1g~butadiene The lowest-energy bonding orbital of an allyl system is shown as an example of the style you should use. ANSWER: (HOMO of 1,3-butadiene) Example 3. (3 pts.) Rank the carbocations below according to their relative stabilities (1 = most stable, 4 = least stable). cha/ Afl> M M 1(%\\Q’l“%3 . ‘(RW‘D 4 (9&3 4. (3 pts.) Show how the synthetic transformation below may be achieved. More than one reaction is require the reagents and products for each reaction separately. - d. Write "3 Chem 308, Summer 2009 NAME Quiz 1 Section H4 1. (2 pts.) Draw the structure of the 1,4-addition product in the reaction below. ignore stereochemistry. Br G\ M ? Qk/g‘ 2. (2 pts.) Draw the two most important additional resonance structures of the anion shown below. 3. (2 pts.) Give the major organic product(s) of the synthetic transformation shown below. ‘ OH cml - conc. H2804, A M7© 4. (4 pts.) Write a detailed mechanism showing only the propagation steps in the radical chain reaction shown below. (NBS = N-bromosuccinimide) NBS, HOOR \\\/\Br V \\N\ ( “g In REY" Va Jr E B(‘ “"5 Jr BC? {an em— W} (lth Chem 308, Summer 2010 Quiz 2 Sections H3 NAME V ID 1. (2 pts.) Circle any AROMATIC'species (molecules or ions) shownbelow. 2. (2 pts.) Draw the structUre of the product of the thermal electrocyclic reaction below. Indicate the product stereochemistry clearly. . CH3 lily; \ - A / \anv | — . CH3 ' CH 3 3. (2 pts.) On the right, draw p-orbital diagrams _showing the HOMO-LUMO interactions in the reaction below. \QSV gar / (:5 A F + H ——-————-n:- E ANSWER:— F ~ \ 31:2 4. (2 pts. Draw the structure of ortho-bromophenol. 0% {/\§\/ Er ‘ . V m; (Cassatt 5. ‘(2 pts.) Draw the structures of the organic reactants that will produce the product below in a Diets-Alder reaction. CH3 \ LN . ON NAME ' ID . ' Chem 308, Summer 2010 ‘ Quiz 2 Sections H4 1. (2 pts.) Circle any AROMATIC molecules shown below. 4 "" [YM 2. (2 pts.) Using the template provided, draw a p-orbital diagram of the Frontier Orbital in the photochemical reaction below. is the reaction conrotatory or disrotatory? / hv i Template \ for answer:— Conrotatory or disrotatory? $\\ 5 Q (\3 3. (2 pts.) How many bonding, nonbonding and antibonding n-molecular orbitals does benzene have? Number of bonding n-molecular orbitals = 3 ER . We 2N Number of nonbonding n-molecular orbitals = 0 Number of antibonding sis-molecular orbitals = ’3 4. (2 pts.) Give the lUPAC name of the compound shown below. - CI (Maharang ~ Qf i"\ (a 5. (2 pts.) Draw the structures of the two organic products of the Diels-Alder reaction below. Indicate their stereochemistries clearly, and label them endo and exo. m3 ‘ n3 CH3 / CN CN ‘ J (Hi l + E —_—-—:—-————> I? ‘ \ ON . (N ’M CW CH3 ‘ V Chg cs3, \M‘MV :93? ...
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Chem 308_Summer 2010_Quiz 1 and 2 keys - Y . ID Chem 308,...

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