Exam+1+Answer+Key

Exam+1+Answer+Key - CH 204 Organic Chemistry Fall Semester...

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Unformatted text preview: CH 204 Organic Chemistry Fall Semester 2011 Professor Newman Exam 1 October 3, 2011 Name g i Page Number Possible Points Points Earned 1 20 2 13 3 12 4 1 1 5 10 6 10 7 10 8 10 Extra Credit 4 1. Provide an appropriate name for the following molecules (2 points each): elsfcmq 0»? “(a IxflXDlho ,‘r— amid 5"}(CPILO‘F'FVCJL/dYDCG-tpf9)‘c “Clio! 2. In the box provided, draw the correct structure for the following names (2 points each): m-nitrobenzoic acid Sfimethoxycaproic acid benzaldehyde 3. Look at each of the following compounds and determine if they are aromatic, antiaromatic or nonaromatic. In the boxes provided, write AR for aromatic, ANTI for antiaromatic, and NON for nonaromatic (2 points each): 4. For each of the following pairs of aromatic compounds, draw a circle around the substrate that would undergo the electrophilic aromatic substitution the fastest (2 points each): 5. Label the following dienes in order of increasing reactivity for the Diels Alder reaction (1 is the fastest and 4 is the slowest) (1 points each): 6. Draw the two major products from the cleavage of the following ethers (2 points each box): Nib" F 7. 1n the boxes provided, write the reagents necessary to complete the transformation shown (2 points each): . f %h/ HCQQ‘D O 9. In the box provided, draw the starting material necessary to for the products shown under the conditions on the reaction arrow (2 points each): B!” 10. Although a haiogenated benzene (like bromo benzene below) is slower than benzene to react with an electrophile (deactivated), the bromine is a orfho/para director. Explain why this is the case rather than being a meta director like other deactivating groups (5 points): 11. Provide a reasonable arrow pushing mechanism for three of the following four transformations. Write the word “OMIT” below the one you do not want graded (if you don’t write OMIT, only the first three will be graded). (5 points each): 0 J? + NO ——>A T/ /N\ is v 1W < \ 11 (cent) Provide a reasonable arrow pushing mechanism for three of the following four transformations. Write the word “OMIT” below the one you do not want graded (if you don’t write OMIT, only the first three will be graded). (5 points each): H3C\© H30 ——-W—'—> H2804 No2 ltd/3N- r3 . , 93 //O Y(/Ukhfi) fl?) 1: 12. Choose three out of the following four and provide the necessary reagents (any inorganic materials needed and any organic molecule with the number of carbons indicated in parentheses) needed to complete the following syntheses. Write the word “OMIT” below the one you do not want graded. (If you don’t write OMIT, only the first two will be graded) (5 points each): ? CH3 0 "—> O H e 1) gm} 1) v 0230152m" 1‘ l2 (cont) Choose three out of the following four and provide the necessary reagents needed to complete the following syntheses (5 points each). l l l o/ 0/ (D ? m OH If) #wiélfll/JS‘OY . O 2.) gn/Hg / Mite—g) ‘14)}! Ml (\jfljt’lNOdj 00 a) bigot M —_?—» WOH Extra Credit 1. Other than the Diels Alder reaction, give the names of two other name reactions that we have learned so far in CH 204 (I point each)? Con (916.351 [alias F/akeoLQ/C-wca al/fi/mlfoh film/mm“ LNLIJON 3 } LJo [Cg )6 Kine/v Rake/IL,» m, 2. Look at the compound below. How many unique signals would be expected in the 13C NMR (1 point): ...
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This note was uploaded on 03/10/2012 for the course CHEM 352 taught by Professor Gierasch during the Spring '12 term at UMBC.

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Exam+1+Answer+Key - CH 204 Organic Chemistry Fall Semester...

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