exam1-key - Organic Chemistry 345 Name (Please write...

Info iconThis preview shows pages 1–7. 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
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Organic Chemistry 345 Name (Please write Clearly) _KeZ___ Stude t ID Home Street number (as in UW Records) Fall 2006 Exam 1a Your Seat Number Question Points Grader’s Initials 1 10 2 10 _ _ 3 20 4 _‘l_ _ 5 ‘1 10 ‘i “I H 11 ‘ q 12 ‘71 13 q 14 H LI 15 4%“ W MW° (2 Points for each Synthetic Question and 4 Points for each Machanism Question) The Blank Last Page is for Scratch Use. Nothing on that Page will be graded. Pg2 Organic Chemistry 345 Fall 2006 Exam 1a ksz Name (Please Write Clearly) 1. Give the produCts of synthesis as isolated after workup. 3‘) ph‘ ,COOH - PA>CH“Q0°H' q —0 Me/ COOH “0 Me oMe, OMe b) Li, t—BuOH ’ i; Liq. NH3 5* c) O 84* —» {‘1 Et Br2 HBI’ cat » OMQ' d) Anisole Q - o PhN02 "O - / CISJ ' -’ _ ~<H ~Q~ e) PhCH=CH-C\=O + NaCN fi> PL‘ Q,“ 3' mg Ph EtOH, HOAc > CA] CH3 1 fl “cooE' f) Benzaldehyde + CH3CHBrCOOEt P "04" CH 1’ Zn, benzene ) OH O O o g) [:3] +CH3fiOOH —> o 1’) Phthalic Anhydride + Isopropylamine \ “kg 0 Mg NHAC 81’ i) Br2,FeBr3 Mb j) Me ‘ ,Qrufi NH2 NH '5 3 PAGE 3 Pg 3 Organic Chemistry 345 Fall 2006 Exam 1a ‘ Name (Plegse Write Clearly) 2. Give the products of synthesis as isolated after workup a) PhCH=O + Ph-C\=O PLM‘f—scH-S-PLL CH3 Conc. NaOH, 0 EtOH b) Benzaldehyde + Ph3P=CH2 . PL-C/H: CH), . 0) Benzyl Alcohol Pk'QH O PCC, CH2012 Me EtOH d) + CH2=CH-C=O / _ \CH ./ O 3 0 e) O ? é/SePh H202 b A—> _ H Ere - f) Ethyl Benzoate —————————> loin 00° H +‘ Aqueous NaOH . COOH __ COO 9) COOH “0 ' I“ h a "Q "CH ) Benzylamine —> f’lx'C/“L ’0“ g 3 A020 ' i) Me—CEN + Cyclohexyllithium —» Wb‘fi‘Q EtzO b j) _ I Cob H 1 pmpamfl Jones' Reagent ate/‘4" CrO3, H2804 (In. £3720“) Pg4 Organic Chemistry 345 Fall 2006 Exam 1a (fey Name (Please Write Clearly) 3. Give the products of synthesis as isolated after workup Dilute NaOH flew a) Ofii—CHZ—COOEt 0?,“ 3 o o b) i-Propyl Benzoate Aqueous NaOH I /O CV13 Succinic Acid —> c) A K I 0,. Me —O . d) PhZCH-Br ," [NM-0H MeOH Q00“ ' p—Bromoanisole W ' ! 2 e) 2) 002 Me O 2 (H —> , - L - g Benzoyl Chloride + PhZCuLi —" P 4%) P h) NHAc NHAQ- -———> Br2 FeBr3 69 O i) 0 1 ——> fij Lithium Diphenyl Cuprate j) NH2 Ml -~—— ) 1)HNo2 - (I Me 2) CuCN Mg, Page 5 Organic Chemistry 345 Fall 2006 Exam 1a Kg Name (Please Write Clearly) 4. a Encircle each of the aromatic species and leave the anti-aromatic ones uncircled. b. For the underlined ones, indicate the number of resonance structures. ®©363A©o©> 3 x 5_ 5. Give the mechanism for the decarboxylation of Ph_fi_CH2_COOH 0 Draw you arrows carefully and put in all charges and unshared electrons. fl. _ “cu m /CH yo; pkg 3 PL-Q’QHL‘t-vg'. P —°/ zP 9" g” "a 551.”? _ I I H/ 6. (A) Carefully draw the Frost—Musulin Circle Mnemonic for Benzene. Label all the parts, put in MO levels, label energies, put in the electrons. Then get the Pi-energy. For part B, get the energy of three isolated double bonds and draw the sets of bonding and antibonding MO’s with the proper number of electrons put in. Then add to get the Pi energy. Pi Energy_=“8 v3! Pi Energy for the 3 Ethylenes = -‘4 C: Now give the Resonance Energy (DE) for Benzene in units of [B[: 2Lvsl 8. Write out the reaction mechanism for electrophilic substitution of Anisole by the electrophile Br+. Show the starting material, the sigma intermediate and the final product. Write each structure clearly with all unshared electrons and formal charges. In the case of the sigma intermediate, write the most important resonance structure. @.. ’ ML ,0 Me :OF,PQ£ ZLQ) Ea ~> 3 r a 1+ V ’ fiéx’fififw B‘r 0* Mild/9M" @ N Malina m amps/AS 6K 31 [W “#9 M ...}.'L€A,lL ‘5 “m (7/97 6 9 . Write out the mechanism for the Birch Reduction of p-Xylene. Put in all charges, odd-electrons, etc. Use ethanol as the alcohol. M MQ, {AK 1 a 2‘9 C 64 film “a [is t #7» 1:2 “’7 M “$3 / fioH M c? M * Mt Mo ML (“£31345 " 10. How many peaks are anticipated in the 1H spectrum of each of thefollowing? (a) t-Butyl Ethyl Ether 3 ' b) p-Nitrotoluene 3 ; (c) Chloroethylene 3 ; (d) Diethyl ether g ;e) 1,4- Dimethoxybenzene 1L 11. Given the series of acid derivatives, number (1 to 5) these in having decreasing double bond character (i.e. number 5 having the least double bond character). Anhydrides Amides Acid Chlorides Carboxylates Esters 12.In the Infrared Spectra of the above acid derivatives (i.e. in Question 11), which derivative will have 7 peak at the highest frequency (i.e. most to the left)?At/J CA,h"d%J . Which will have a peak at the lowest frequency?' Q}rLgxil§+ég . l3.Write out the reaction mechanism for conversion of ethyl benzoate to benzamide by reaction with ammonia. Show the starting material, the sigma intermediate and the final product. Write each structure clearly with all unshared electrons and formal charges.intermediate. : [I “'3 NHL. " . - i ,. _ /'UH3- +. E’f pkgfira ——-> Me‘s-(git *7 PL W 1% MM .. g. . . . -_ 0'. _‘ v. ' wt (L 9' fr (2%. km WWW“: 8% w “flights/z; “" 14 . In p-Xylene the methyl peak(s) appear(s) as a SUM/"f (singletdoublet, triplet, quartet). 15 . An unknown compound, X, is found by mass spec to have the formula of CsH4NCl. It has a delta value of 3 giving a total of ft rings and double bonds. It has two peaks in the NMR, each split into a doublet. Suggest a structure. C" of uw . H /’ fl )1. THIS PAGE TO BE USED FOR SCRATCH — NOTHING ON THIS PAGE WILL BE GRADED ...
View Full Document

Page1 / 7

exam1-key - Organic Chemistry 345 Name (Please write...

This preview shows document pages 1 - 7. Sign up to view the full document.

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