Final_key1 - ,(a/me: First Last‘h‘QQLAV CWID: m Seat...

Info iconThis preview shows pages 1–14. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 10
Background image of page 11

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 12
Background image of page 13

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 14
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: ,(a/me: First Last‘h‘QQLAV CWID: m Seat Number: Chemistry 3053 Final Exam, 200 points Monday, December 12, 2011 GENERAL INSTRUCTIONS: ) Write name, CWlD, and seat number on this page ) Check for 14 pages (including this one and the last page with the periodic table). ) Sign the attendance sheet when you turn in your exam. 4) Keep your exam flat on the desk in front of you. 1 2 3 You may only have a writing utensil. EVERYTHlNG ELSE MUST BE PUT AWAY. No cell phones No calculators No electronic devices of any kind. Show Your Work. Be Specific With Your Answers and Write Leginy (if we can’t read it, we can’t grade it) GOOD LUCK When your exam is returned, your score will be on the last page. 1 Page Point Total 1) Fill in the boxes with the major product formed from each reaction. (16 points) HBr 1) NaH 1) MsCl, pyridine ‘——-— ——_—_____> M GA 2) MOI—l M . /\Br 2) CH30‘ H2804 140 C M 0 Ah 2) Propose a reasonable arrow pushing mechanism that accounts for the following transformation. (5 points) OH .\‘O\/ Q , \ 96 i ME = H‘fi “Eb v7 I 53 [AD 0 2 Page Point Total 3) Fill in the blanks with a reagent(s) that would afford the given product as the major product. (15 points) ‘to 0‘ I a d) 3 Page Point Total 4) a) Give the products of the following reaction: (6 points) b) Identify the isomeric relationship of the products from part a: (2 points) c) For any chiral centers in the compounds from part a, CLEARLY designate R and/or S stereochemistry: (8 points) c = Q A=S Pgflad 033 d) Convert your products from part a into the Newman projections with the lowest energy staggered conformation, looking down bond C3-C4. (6 points) 4 Page Point Total 5) Give a reasonable starting material that could afford the given product as the major product under the reaction conditions provided. (12 points) a) ___—Ifl—~_> |/\J\/\l ‘0 b) L E) 7 OH NaBH4 —-—-———> NaOH g? OH 555 ur' ouwnzs good \rcowmg 6) Show how the given product could be synthesized from the given starting material. a) (9 points) Br (jk/ l: “BRO, = Reagent 5 Page Point Totéil b) (9 points) CH2 (j 6A3” = ‘Reagent O/\CI Ma 5“ - = Reagent = Product L) 7) Given the following information, give the structures for unknown compounds A, B, and C. (15 points) MgBr 1) CH3 HO CH3 A: C10H180 “fl 2)H30+ NaBH4 PBr3 6 Page Point Totél 8) Give a Grignard Reagent and a carbonyl that could prepare the given alcohol? (12 points) a) j _ Grlgnard Reagent carbonyl V W 5‘6 '1 5 OH (W ——-——» 3 3/ b) Grignard Reagent carbonyl W 0/ H20 + HBr H3O+ + Br. 7 Page Point Total 10) For each pair below, state whether the two compounds are enantiomers, diastereomers, conformational isomers, structural isomers or identical compounds (you may use some definitions more than once and others not at all). (12 points) A CH3 g 0 ) fl wow CH3 CH3 B) CH3 CH3 C) Br if?» Br/\/k/ \/'\/\Br 1d}: CC! D) A)? fBr h . M 6m /\O/H\ 11) Mark the letter answer leginy (A, B, C, or D) for each question in the blank to the left. (20 points) A a) Identify the compound that violates the “octet” rule? A) B) C) D) >:é M H32}: NBr OH 0 0) Identify which compound is a Lewis Acid. A) CH4 B) NH4+ C) BCI3 D) “OH 8 Page Point Total C l d) identify which compound is 2,4—dimethyl—3-isopropyloctane. “1w 89$)wa A e) identify the lowest energy conformer from the following Newman Projections. B c D “®“ Q; 319;? E9 3 H H H H H H H H H CH3 H30 H H C t) identify which anion would be the worst leaving group. A) F' B) 'OH C) 'CH3 D) l' A 9) identify which anion would be the least nucleophilic in protic solvents. A) F' B) l' C) Br' D) Cl' C h) For the following acid catalyzed dehydration reaction, identify the MAJOR product. “OH st04 heat A) B) C) D) or 6/ “K N C i) Identify the haloacid that is most reactive in hydrohalogenations (addition of HX) A) H—Br B) H-Cl C) H—I D) H—F E 2 j) Identify which conditions would afford the alkyne from the alkene. 1) '27? __ 2) ??? r ———-——-—> III A) B) C) D) 1) 012 1) H3O+ 1) H-Br 1) Bra 2) NaOH (excess) 2) H_Br 2) NaOH (excess) 2) NaNH2 (excess) 9 Page Point Total 12) Give the structure that corresponds to the following IUPAC name. (12 points) a) (Z)—But—2—en-1—ol /\ HO f b) 2-Chlorohex-3—yn-1-ol \XO 0) 2—ethoxypentane Dex: N1" 13) Give the word that corresponds to the given definition: (9 points) a) A solvent that contains an H that is attached to an O or N: jgl i S C» b) The molecule or ion that undergoes the reaction: figébfl g& c) An addition that places both parts of the adding reagent on the same face of the reactant: 10 Page Point Total 14) a) Explain why the following reaction does not give the indicated product. (6 points) JV dil. H2804 M / Y OH b) What could be done or changed to synthesize the desired product. (5 points) W .3395 owns“ 15) a) Draw a chair conformation of cis-1,4-dimethylcyclohexane and its ring flipped conformational ' . 4 ' ts Isomer ( pom ) 0‘») 04.5 k I {3%} (“'— b) Draw a chair conformation of trans-1,4-dimethylcyclohexane and its ring flipped conformational isomer. (4 points) (/95 (/9 3% "A CH1 <~ ' CA J 11 Page Point Total 0) Which compound is expected to be more stable: Cis-1,4—dimethylcyclohexane or trans-1,4— dimethylcyclohexane. Explain your reasoning. (4 points) Extra Credit 1 (4 points) Give something you liked about the course and also something that could be improved for next semester. 12 Page Point Total Extra Credit 2: (10 points) Given the following retrosynthetic analysis, show how to synthesize the target molecule from the two starting alcohols. OH W l Ci j 13 Page Point Total Scratch Paper Only — Nothing written on this page will be graded. u w sxxslnm periodic table of the elements I mm, — Elemm Arozm: .~—- 3 Number _. Symbol Atomic fitjf‘im. \Veigm 11 Na Rb 625 4a: a; a? xsml macaw. 72 73 ' 1s 71 Hf TaW 49 ’lfiflfl‘ 183.154 piler 72 = m a Iimxilisw‘rx‘lfillx mom thaws gnaheil: clematis Score: «W. mam??? T 32 53 i - mstEu’ r WWW mwmw, M : sy Le var: nan cam: «we: 28 2E! 36 ' Cu Zn mm (was be' - lzuum my 'mlun f a??? 3‘3 69 $3? gx 79 Au mmls not metals ml: kite gases 18 halagms «magma 1 Semlmex film; “@3er ' as H éEr i “a g > » Rndxt‘nzmva mgmé Mag M A ; "Ea; L r: 14 Page Point Total ...
View Full Document

Page1 / 14

Final_key1 - ,(a/me: First Last‘h‘QQLAV CWID: m Seat...

This preview shows document pages 1 - 14. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online