CHEM%2311)M%%%%%%%%%%%%%%%%%%% ! !!!!!Last,!First!Name!(Print)!_________________________!Fall%2014%%%%%%%Exam%1)1%Key! !!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!GTID_________________________! 1. (12 pts) For the compound shown to the right: !Use an A to label the cis double bond(s) Use a B to label the trans double bond(s) Use a C to label the alcohol group(s)! Use a D to label the methyl group(s) Use an E to label the carbonyl group(s) Circle the phenyl group(s) 2. (10 pts) Draw the bond-line structure of CH3C(O)CH2CCCH2Cl indicating 3-dimensionality by the use of dashed and wedged bonds. Draw out hydrogens. Be sure to include all lone pairs and formal charges (if any). 3. (6 pts) Draw the complete Lewis (dash formula) structure for methylpropanoate (CH3CH2CO2CH3). Be sure to include all lone pairs and formal charges (if any). 4. Resonance a) (6 pts) Draw the resonance structure that would result from moving the electrons as indicated by the curved arrows. Be sure to include all lone pairs and formal charges (if any). !NOOFFHOOHABCDECOOCCCHHHHHHH HClH HOHHHHHb) (10 pts) Assume that Br spontaneously leaves the molecule below via heterolytic cleavage as the bromide anion. Draw the resulting molecule in box A. Then draw two resonance structures in boxes B and C. Use “curved arrows” to show the electron shifts. ! !!!! 5. (12 pts) Organic peroxides with the general structure RO-OR are known to homolytically cleave at the weak oxygen-oxygen bond. Draw a mechanism using the general RO-OR structure that portrays this cleavage above the line shown below. Then show how one molecule of the reactive intermediate formed reacts with a molecule of ethene (C2H4) below the line. 6. (10 pts) For the compound shown below, identify the: a) Number of sp3 hybridized carbon atoms:__0__ b) Number of sp2 hybridized carbon atoms:__7__ c) Number of sp hybridized carbon atoms:__2__ d) Number of σ bonds to carbon atoms:__16_ e) Number of π bonds to carbon atoms:__6__ CO2H!!!BrA%B%C%RO OR2RO2RORO7. (8 pts) For the compound below indicate the number of primary, secondary, tertiary, and quaternary carbon atoms. 8. (4 pts) According to molecular orbital theory, which molecule could not exist? Circle the letter that corresponds to the correct answer. a) H2 b) He2 c) Li2 d) F2 e) N2 9. (10 pts) Referring to the compounds shown below, answer the following questions: i) Which compound(s) have aromatic groups?_______________B, C_______________ ii) Which compound(s) are ethers?__________________B_______________________ iii) Which compound(s) have nitro groups?_________________C_________________ iv) Which compound(s) are tertiary amines?______________B___________________ v) Which compound(s) are alcohols?_________________A, B____________________ 10. The structure of ethene is CH2=CH2 a) (2 pts) Draw the structure of the product formed from the addition of Br2 to ethene. b) (2 pts) Draw the structure of the product formed from the reduction of ethene with H2. !!! 11. Draw bond-line structures for the following two condensed formulas. Be sure to include all lone pairs and formal charges (if any). a) (4 pts) (C2H5)2C=CH-CHO b) (4 pts) (CH3)2CH-C6H4-CH3 !Number of 1° carbon atoms:__2__ Number of 2° carbon atoms:__5__ Number of 3° carbon atoms:__2__ Number of 4° carbon atoms:__1__ OHOOHNCH3MorphineBOO2NNitrophenylpentadiene aldehyde (NPPD)COHCH3CH3H3CCH3CH3Vitamin
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