Problem_Sets_Key - First Name: Last Name: UTEID: SCORE: KEY...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for CH310N POW 1: Jan 31 3:00 PM 1) For the following structures, label the equivalent protons with the "a, b, c" lettering system. COOH O CH 3 O Asprin (salicylic acid) O a b c d e f a b CH 3 C H 2 O C H 2 CH 3 a b c d e a a b b c c N H O a b c d
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2) Assign the splitting pattern to each type of protons in these structures. Use the following abbreviations: s= singlet; d=doublet; t=triplet; q=quartet; 5 or more peaks: multiplet. If there is coupling from different sets of protons, then both couplings must be identified. E.G. doublet of triplets: d of t or t of d. CH 3 C H 2 O C H 2 H 2 C CH 3 triplet triplet triplet quartet triplet of quartets (12 peaks) H 3 C H 2 C O C CH 3 O triplet quartet singlet
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Last Name: UTEID: First Name: SCORE: KEY Deadline for CH310N POW 2: Feb 7 3:00 PM Cl C H 2 H 2 C C H 2 Cl Cl H C H 2 C CH 3 Cl 1) The NMRs of three isomers of dichloropropane are shown below. Match each compound with it's NMR and provide an interpretation of each spectrum. (i.e. draw the structure on the NMR and label protons, with their splitting.) H 3 C C CH 3 Cl Cl 0 1 2 3 PPM H 3 C C CH 3 Cl Cl a a a, singlet
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0 1 2 3 4 PPM 2 4 Cl C H 2 H 2 C C H 2 Cl a, triplet a, triplet a b, pentet b 0 1 2 3 4 5 6 PPM 3 2 1 Cl H C H 2 C CH 3 Cl a a, triplet b b, d of q c, triplet c 8 peaks
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Last Name: First Name: UTEID: SCORE: KEY Deadline for CH310N POW 3: Feb 14 3:00 PM 1) Grignard reagents: Provide the products for the following reactions. ( structure-n-a-box ). If there is stereo- or regiochemistry in the products, you must indicate it with the appropriate drawings, such as wedge and dashed bonds. O H 1) CH 3 CH 2 MgBr 2) H 3 O + OH CH 2 CH 3 O CH 2 H 3 C 1) CH 3 CH 2 MgBr 2) H 3 O + H OH CH 2 H 3 C H CH 2 CH 3 O 1) PhMgBr 2) H 3 O + OH Ph a) b) c)
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2) Grignard reagents: Provide the reagents for the following reactions. If more than one step is required (e.g. acid) you must show it. O CH 3 OH CH 3 1) PhMgBr 2) H 3 O + a) b) c) CH 3 O CH 3 OH 1) CH 3 CH 2 CH 2 MgBr 2) H 3 O + MgBr O OH 1) 2) H 3 O + d) MgBr 1) CH 2 O (formaldehyde) 2) H 3 O + OH
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Deadline for CH310N POW 4: Feb 21 3:00 PM Multi-step synthesis: Provide products for the following sequence of reactions. Draw each product in the box (structure-n-a-box) provided and indicate stereochemistry, if any is involved . (Hint: ref er to Rxn Summary handout) Br 2 h Br KOtBu HOtBu O ArCO 3 H CH 2 Cl 2 MgBr 1) 2) H 3 O + OH Ph Must show correct stereochemistry Must show correct stereochemistry
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A) H 3 C CH 3 CHCl 3 tBuO - K + B) Br 2 CuLi H 3
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This note was uploaded on 09/19/2011 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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Problem_Sets_Key - First Name: Last Name: UTEID: SCORE: KEY...

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