Chem 255 Final

Chem 255 Final - FQQQ Q0630 am 1 Provide the 11m structures...

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Unformatted text preview: FQQQ Q0630 am 1. Provide the 11m structures of the following compounds: (24 pts) (a) butylisopropylether M 0 Y (b) 5-methyl-1,3-cycloheptadiene \ / a 14) (c) E-3-chloro-3-hexene M cl \__./ \/~\/ ((1) 5-hexyn—2-ol 2. Provide the IUPAC names for the following structures: (24 pts) (a) 0\/ O €M°X C (foxexm (b) | 3/)\6/\r y 3 4" Aroma ‘ ‘5’ g 3’ - *rTN/‘y/ odang Br (0) \L H '—‘ ‘ , q é (d) 1CH3 H 1 oH ‘ 0H ’CHZOH (D 3. Provide the hybridization of the atomic orbitals for 2_1_l_l non-hydrogen atoms. (17 pts) 3 (a) if (b) (C) OH 3 7/7 57 3 ,3 3/7: 3”! sfm H l—‘/ t/ 37‘ 5ft 1. 0/ 5/ E :l ——'—\_.__ l H 7’» V Sf) 3/ R 7/"L O 1, 5f T "‘ y‘ 4 K 3 is 5/ 5/0 4. Rank the acidities of the following molecules in terms of their pKa values (from high to low) and provide a detailed explanation for your choice based on one of the following (inductive effect, electronegativity, resonance, orbital hybridization, bond dissociation energy). Provide structures to support your rationale. (30 pts) (a) HC: H20: CH2 H3 C.“— CH3 A B c c > 0 > A *— _—— 4 [a ,- highest lowest 5/ 5 M c pKa pKa 5 do malt , e 6/ a ACga‘l‘zA’ Ck”? l‘l’ Cr: 2 Q’- — C—\ 912’ sf 6 5) T 7' I» (/‘m‘ 571 f At 3/; 3/ 3 (5 our“ 5 ’1‘ ) " [VJ ‘flJJJ‘ ) an S o ,1 7 (B/ ( ’,' Caaq‘yaa'zfi Ang 6) 71,. mad (acidic proton is drawn in) A B C \0‘ 0 B > A > C K ' _— _ ‘\/> ,1 94¢er highest lowest é) eh, 7). 5. Circle the compound that: (10 pts) (a) is the most soluble in water (b) has the highest boiling point we /\0/ N 6. Draw the Newman projection for the lowest energy conformation of 2-methylbutane looking down the C2-C3 bond. (15 pts) CH0 H —OH HO —H CHZOH 8. Draw the lowest energy chair conformation of cis-1-tert-butyl-Z-methylcyclohexane showing all axial and equatorial hydrogens. (21 pts) 9. Designate whether the following pairs of compounds are enatiomers, diastereomers or identical. (20 pts) (a) (b) 1?r H C] H m Wm Wa/ (C) (d) ECH3 gH3 H— Br Br— H H» Br Br»- H %3H3 %2H3 IJCAin'Ca.’ 10. Draw all five of the constitutional isomers for cycloalkanes of the molecular formula C5H10. (20 pts) a“ an \2/ / 11. Show the 2 different pairs of reagents that could be used to synthesize the molecule below by the Williamson Ether synthesis. Circle the pair that would be most likely to provide the desired ether product, and provide a brief rationale for your choice. (14 pts) \/ /\0/\ [3/ wfl/{ampn E%’ 57" fl”) [grocerer V74 c“ 5/01 AW»: 3". ,3, (.yL‘ /.v fJ(’GAI‘$G flaw") 3”?) W :5 &_ /oa* EJ -4 m q /:/7"'~-”u 6"!” ‘ ‘ [zeéflg {A A yaw/J am; An; /e.rJ7 71., 6/544 :44 filn’fi 12. Predict the product of the following reactions. (15 pts) a) HBr ’4 > 5/ b) H20 H -——-——> \/ Hgso4 /Y st04 0 0) H2CTO4 l3. Predict the starting material needed to produce the following product. (15 pts) a) peroxy- / I —-—-——> o l carboxylic I acid b) 4 1. BH3 A 2. H202 NaOH H2 \_ / "“*—E'-'~ \ Lindlar's Catalyst H H 14. Predict the reagents needed to produce the following product. (15 pts) a) OH /0 ‘owl ’ DC ————.—> b) c f/ 1' ___e 7" __ __ _ C) /V (3 S ’ 6%..) l Br 15. Fill in the reagents and starting materials needed for the 2 step conversion of A into B (Remember to work backwardsl). (15 pts) on A B 16. Circle the correct answer: (10 pts) (a) would the following reaction go through an E1 or E2 process: H20 > /\/ (b) would the following reaction go through an Snl or Sn2 process: Nal +Br ——» +1 @ 10 17. Provide a mechanistic rationale for the formation of the following product (structures only - no words). (20 pts) Extra Credit: Classify the following reactions as oxidation, reduction, elimination or substitution: (20 pts) (3) N a —E—-— ——-——» — fl 51., c} D n N H 3 (b) 11 ...
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Chem 255 Final - FQQQ Q0630 am 1 Provide the 11m structures...

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