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Chem335.Exam4.AnswerKey.pdf

Chem335.Exam4.AnswerKey.pdf - 1(20 points Please provide or...

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Unformatted text preview: 1. (20 points) Please provide or cincle the correct answer for each questions below. Only one answer will be accepted. A) Please draw 2-fluoro-N-methylhexan-3-amine. /\fi:1/ F B) For the each of the 5 problems below, circle the mom acidic bolded hydrogen. Note that each molecule is drawn twice (the first structure being the standard bond line form and second depicting the hydrogens at each position). Circle only one hydrogen in the second structure. An example is provided. 0 o l) 0 @fig III 322:; I>=o III I) e @= ., m 99 C) I Z: ::' :5 I—\ Z 0 lg: I m WW, I o 0 iv) 0 HO Jl\/\",NH2 o H o C) Please rank the following compounds by basicity. 2/13 E) Which of the following statements concerning the amines is false? i) Quaternary amines are positively charged at nitmgen ii _. Hydrogens bonded to nitrogen typically display a broad signal in 1H NMR (E) Amines are generally electrophilic ' Nitrogen is typically spa hybridized F) In the 1H—NMR spectrum below, please fill in the letter in each box that is most consistent with the shown structure. 3/13 2. (20 points) Please provide mechanisms for the following transformations. “Han -CH3 0 ° 1)HGI. EtOH. A moon/KL NaBHsCN 1)NaO§LMe_____+W'\EtOl-i YKJOL___._ 2) NaOH H20 2) H30 5491 sfim Star? 5. ® 34‘9”“- ® Q/‘Nw we” we Hum- qt» /” “0 We fl” .3. l ‘CQ H MM“; / «as» t: "f H H V“ o to Q g 43 J? J k ‘56 6’" H H I {It :3. fin?» )r ax‘sfij’iv #J if? I W. M N its» / e t (\\ lw/ If necessary, please continue mechanisms onto the next page 4/13 Mechanisms (continued) 5/13 3A. (9 points) Draw only the major product for each of the reactions. Note: one answer will be accepted and no points will be awarded if multiple answers are given. 0 i) . 1) LIAIH4 NH é 2) H30. 1) NaNs 2) UNH‘ 3) H30 B. (6 points) Draw the starting materials that would lead to the shown product by a reductive amination. Reductive Amination i) (P: .. Fleductive ") o Amination O (3 6/13 4A. (9 points) Draw only the major product for each of the reactions. Note: one answer will be accepted and no points will be awarded if multiple answers are given. ii) 0 + o 1) NaOEt, EtOH NU —-———* iii) Mag 1) NaOEt, EtOH fl EtO _ _ o 2) 1430' B. (6 points) Draw the starting materials that would lead to the shown product by a Claisen condensation. Claisen t ‘ 0i?” )ffo Condensation Claisen (a ‘Q flog/Nah: Condensation /\ O ()1 fit) zl\f‘-nl>i’\ 7/13 5. (20 points) Provide the information that has been omitted in the sequences. 1) NI l H2 +—-— 2) Para 3) FeBrs Bra Han...” hMéi/Eofi'l‘ar Formula: OWENéOa 1) H2304, A 2) Zn. TiCI4 6. (10 points) Suggest a multi-step sequence that allows for the conversion of the following starting materials to the corresponding products. (Note: any additional starting materials can be used that contain 2 carbons or less) 0 O . . ‘7 awn-4. CGWI W W ‘33 ‘3‘th W/U‘“ 1); W/UVNHZ he mm of law a Rub; W1 W. [—5, Q am, 3 I} as, We,” WW” ”2%” §)H36-’ Z) +50% Answer #23 09%? 8 /® . Br 0 “”2 MW“? ‘4 «()7 Bf ) O/Br ___/_) V 72%: 7% ” :0; Mat ”709 W {43 /_-. «9 no on 0 MAC cal WM! P“; l m1 1. o a 7/54 NH 27)\/ 2. 7) H 1314;? H ”Hag” WEB W 30 CH W3 Ll)” mt ”are: g x. \ , z “ 7/ Hal/730*" / M2 M5?! 9/13 Extra Credit Page E1. (1 point) What is the pKa (:I: 1) of a typical B—ketoester? l l E2. (1.5 points) Draw the following molecule in both of its chair conformations. Circle the conformation that would be favored. //”——\ . ""\ .\ .————> 3/\/\}< \\ s"? \ : \anw ,,.,r . _ . E3. (2 pts) Suggest a mechanism for the formation of the product shown below. Partial credit will be given for reasonable initial steps. ””2 )LH \ ”/1, ”\® ../ it? :12; QUNQ & E; :1 figs \ L Ho “9 9th 10/13 ...
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