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2008ochemexam 2

2008ochemexam 2 - KEY NAME CHEMISTRY 2211 EXAM 2 Be sure to...

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Unformatted text preview: KEY NAME CHEMISTRY 2211 EXAM 2 February 27, 2008 Be sure to read each question carefully. Partial credit will be assigned where appropriate. SCORE This test mgst be taken in gen. Pencil exam; fl]! not be graded: Good lucid! g l. (10 points) The sex attractant of the cooling moth is the 22, 6E stereoisomer of 1' U3 CH30H20H2?=CHCHQCH2(I3:CHCH20H 2- cua CH20H3 3. Write the structure of this substance that clearly shows its stereochemisn'y. 4. E I: A growth hormone from the cecropia moth has the structure shown. Express the stereochemistry of the double bonds according to the 5-2 system. 7' :1" CHch3 CH20H3 CH3 3- 3 7“ 3x COOCH3 O 6 2 6’7 2'3 mTAL I O 2. 114’ points) Draw and give IUPAC names for 5 isomers of C4113. Structure: Fig.6.: C H CH 3. CH3 Namezmm-HLOICLDPRDPANE Name: I—‘bUTENE 2 3. (15 points) Use the reaction diagram below to answer the following questions. Reaction Progress Answer the following questions by writing a letter from the diagram. This step is exergonic. This transition state represents the smallest AG * . t This transition state represents the greatest ’30 . E The reaction intermediate is found here. This step is endergonic. Overall this reaction is EX E R 50 N I Q (exergonic or endergonic.) 3 4. (15 points) Consider rotation about the C3—C4 bond of 2,3-dimethylhexane. Carbon 2 is identified on the Newman structures. Complete the structure by drawing the Newman projection of the most stable conformer. CH | HCH3 C2 H H H CH3 c-HgCHz Complete the Somme by drawing the Newman projection of the least stable conformer. 6"ng c2 CH3 Cpl-$3 H Draw the Newman projection with the (LEGS: gauche interactions. 3 H c2CHC 3 H CH aCH} H CH3 4 5. (10 points) Draw the most stable chair conformer of cis-l-ethyl-2-isopropylcyclohexane. Carbon 1 is identified. at“: QHSCH ( esp. / CHLc-H 3 Draw the most stable chair conformer of trans- l-I-butyl-3-methylcyclohexane. Carbon 1 is identified. ( ea) ( CI-Qsc / C1 CH3 (cu?) 6. (12 points) Using the cyclobutane templates provided below, draw structures for the monochlorinated products resulting from the following radical halogen-won. Hint: Be sure to consider all possible types of isomers. ”3 Cf + Cl2 hv momc hlorinated products (3";ch D4” U": EL». U CH3 ’CH5 \ CR- co. 5 . (12 points) Draw the lowest energy chair conformation of the following substituted cyclohexanes on the template that is provided to the right of each structure. H :.-CH3 ( fig.) ”lie-q.) 043 (in; C1 / CH: ( ”H c: ( an «Q CF. CH (CH 3) a. CHlCHs): C1 / (an (ea-t CH3 CH 3 Q NOT amass HO H Jest-3 0H (e40 H 0 OH (cg) t as) net.» C1 ' ' D (m) D-Pinotol a hexahydroxy cyclohexane What is the total number of gauche —0H interactions in the lowest energy conformation ofD—Pinotol? What is the total number of 1,3—diaxial -—OH interactions in the lowest energy conformation of D-Pinotol? 6 8. (8 points) Identify the following reactions as additions, eliminations, substitutions, or rearrangements: CHgCHzBr + NaCN——-- CH3CH2CN + NaBr SUESTITUTI on RDDITION no, 0 + OZN—NO2 J&"‘———- O] + HNO; SU‘E‘le‘T’UTlON 9. (8 points) Add curved arrows to the following reaction to indicate the flow of electrons. rd H H &?H~CI ggk = Ckicng l («9 CH3 (:16 ...
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