Organic Practice Problems Answer Key - Summer 2017

Organic Practice Problems Answer Key - Summer 2017 - CHM...

Info icon This preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

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

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

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

View Full Document Right Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: CHM 3218/5305 Summer 2017 Organic Practice Problems 1. Using Newman projections, draw each of the following molecules in its most stable conformation with respect to the indicated bond a) 2—methy1butane, C2—C3 bond an - on} 3 (““3 [boxh on. teo\uo\\LnL JV :“3 CH3 / H _‘ \4 u \ LHS 3 ‘ \V') 660,3“) KN. H \ CH3 CH3 b) 2,2-dimethylpentane, C3-C4 bond. cu cu “WA“; (wt Q-thil one manta X3 H 5 \§ \ I \‘l €3IOV?§ (Vt. Q) C(V mvc‘lt ‘ 3 Jr] 3 H ‘ H CD For: x ‘ ~ “ CH 2. What are the stereochemical relations (identical, enantiomers, diastereomers) between the following four molecules? Show the absolute configurations at each stereocenter. HCH; Hts) HGH:l H HCS) H (>) HCH:l OCH3 HCH3 ‘3.Qs\-uuamv \btmhcul Lhan‘40m'a 3. Give the major product from each of the following reactions. If no reaction is expected, write £6NR99. CH H2, Pt/C Lb/UA) Lb/ 3 __.> rib-l H1 a )5)? LCM M lL§5 h‘fibbvtb CCU JG? w GAMMA, O O “é H o > M _>NaBH4 M ’ «awn-nu. m‘x’VWK' ““3““ I CH3 OEt EtOH CH3 0&1" l’OO wet“, ‘4) VQIJLA. \Ivu. 15W [fl 0 H+ o o é + HO/\/0H —> El 3 CH3 (N am an, ”‘4; VA CH3)\/CHO + NH4 CI + NaCN —> {343 N\:‘.5N (\m‘ CH5 4 ) H < > HCI H -—-—\/\ CH CV”: man; QXGBLL — [ 0—K” U 3 3° ‘0 V ) CH (9 Q COW ace. \0 h 3 CH3 A . O u Lab CH{/\NH2,H+ ~———> OCH3 H 0+ ® 0,05 (K ‘4 <O\<H \ -—> O 0 l NaOH 6H ) H (\n\¢qmo\,Lc.u\o¢ o\'bo\ VLQC,\\CW\ O CHg/N‘CH3 O 0 <3 m O CH3NH2, A @L :‘3’ 3 A» @N‘CHS ————-> Co\.\ \ z o O o é + / CH3 flaO_H, / Q Wm“ WM mm») 0 \/ O 4. Use curved arrows to show mechanisms for the following reactions. Be sure to clearly indicate the electron flow and all charges. H s o - Al O \/3\l N (‘3‘ 2L (3' N \ __.3 G) H \—"' \ NH2 0 NaOCH3 CO CH b) HSCOZCNCOZCHg, W 2 3 O o {‘50 CC C? _ “3 ecu ._~. Q&/\ ow3 Q' CH’SU/CW n 3 CH .50 A? :1 , Ir: H H O O Cum3 CH3é®j CHéo O "(-9 a H O :02 O O (O { 0H 90 1 m c? (M 1 ‘) .4 (3 33M?“ ‘—- (:rV/Ws :2 Wu: H ‘21:}. O V” H “’03“ \—\ ”:0 (a '- \-\ ; o 9 <3 5 (’06 c; e ‘ KH \‘\ $0 Q0 00 H o )1 Q“ (j e: u—fi—‘b ——% “£914 CH3 H 0+ 0 0 d) o ——>3 b + CH3/U\CH3 I ’CH3 CH3 CH3 CH3 1 cu) 0*: can \ , , u-o‘ _, 4 CH Aka-0"” L‘ l O “'0’” ‘— ‘Q »= H :3 \ ’3 3 CH} or ‘N /\ 1 \ Ll \ at)” H H en 63 CH H CH3 "4 tn 3 3 CH3 o® j on, Q” 3 ML? )4 CH, CH) '0,“ CH“ x \ L1 \ ’1 H :3 \owm‘) :-——* i 0" V v. \0 u 63 H ® H 0 CH3 0) CH} W0") \\\ \ \ »/ CH CH} H H H ”3; 4 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern