2008_06_06_14_24_19

2008_06_06_14_24_19 - Please print the following...

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Unformatted text preview: Please print the following information clearly Last Name: '_ First Name“ Student ID: __ CHEMISTRY 140 C (Winter 2008) ‘ Midterm II, February 27th Read these instructions carefully: No notes or calculators are allowed Do not open this exam until told to start You must stop when asked to do so. Written responses must be neat and in complete sentences. Please fill out the top of this sheet clearly. PuePNr' Questions: Points Problem 1 (24 points) Problem 2 (36 points) Problem 3 (24 points) Problem 4 (16 points) Total (100 pts) ‘ All the best Dr. Nefzi Scratch paper Student Name: Problem 1 Propose synthetic strategies for the following reactions with detailed mechanisms. Provide all the reagent and intermediates needed. A) ' . I . _ I If ‘I < .. \_ ' ' E x “(-75. 2- ~ \ I 5» / /;.".. a . \_ \‘ If I r t-“F 2" 5 K H‘" ,1” "l II:- _ l- _ f a \ 'I. U" ' l P“. -_ . . 'I a. -_-' . t 1 L. F Mix A""‘ l ' ' '._ 1i Problem 2 A) COmplete the following reactions: (2? points) Br x9?"- Na+NH2/ ff. 3) I \* —NHL l \ / N 0/ k‘f/‘O/ IN: 3_.\\ H 0 N H+ b) NH2 + —-b- o heal O HCUEtOH c) + +HN heat >/_\ Na+NH2 #‘ d) / \N /NH3 I, \\ _ heat “Maul O ) NHz A :13 \l\ e ———)-— reflux \FK OX J OH 0 Br 8 n CH —» NH; THF, heat Student Name: in DCM —)- 2) LiALquTHF 3) MeOHIH+ /. /' 3) H+IH20 I" f" ioJ‘L DMF Student Name:_ Problem 3 .. - A) Starting from pyridine, provide a strategy for the following reaction using enly'iLDA, ethyllithium and methyl iodide as reagents. - EH 1.": 1 \ ? \ —+ N/ I +’ '_ i ! \ \.. B) Starting from benzaldhyde, provide a synthetic strategy for the formation of the following u-hydroxy carbonyl. Chow all the intermediates and reagents needed. Student Mum Problem 4 Provide the chair conformations, the cyclic fisher projections and the Hawonh conformations for the CL- and [3- fonns of the following monosacchan‘de. Provide a name for this monosaccharide. CHO Hh—OH H——OH H——OH Hfi—OH D_{1\\dmkexuSC"_/\, (“in H’ 1* *4 'i/O / / 'l H {1 DH H OH I OH O a»: 0H CH- H a OR (ITS/‘3 I; I 011 but H OH \ (W on 6” ...
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This note was uploaded on 07/09/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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2008_06_06_14_24_19 - Please print the following...

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