New version page

U of M CHEM 210 - Key 5

Documents in this Course
Key 4

Key 4

6 pages

Key 3

Key 3

6 pages

Key 2

Key 2

6 pages

Key 1

Key 1

6 pages

Load more

This preview shows page 1-2 out of 6 pages.

View Full Document
View Full Document

End of preview. Want to read all 6 pages?

Upload your study docs or become a GradeBuddy member to access this document.

View Full Document
Unformatted text preview:

I. (40 points)Name _______________________Page 1C.ONH2NNprocainamide Predict how procainamide will react in the following chemical transformations. Be sure to use the information given and provide only the information requested.HBr1 equivalentONH2NHNHBrH(a) Balance your reactionCH3BrONH2NHNCH32 equivalents(b) Draw the product with formula C15H26N3O+FeBr3Procainamide is a drug used to treat cardiac arrhythmias.OH2NNNHC1C2procainamideThe rotation of the C1-C2 bond labeled in the structure at left is influenced by a specific intramolecular interaction that stabilizes some conformation(s). Draw a Newman projection for a staggered conformation of this bond in procainamide, clearly indicating the intramolecular interaction that occurs; you should view down the C1-C2 bond with C1 in front.HNHNHHHONH2A.connectivity and conformation must be correct for 5 pts - 2 pts for showing the only one H bond carefully7B.55N is more nucleophilic than the aromatic ringonly this structure (-2 if they miss the charge)The treatment of alcohols with BF3 is one method used to generate carbocations for electrophilic aromatic substitution reactions. This method was used to effect the transformation of Compound 1 to Compound 2 as shown below. Show the most straightforward, complete, curved arrow mechanism for this transformation using :B abd HB+ as needed (one rearrangement step is necessary and stereochemistry may be ignored).BFFFOHCompound 1Compound 2 (other byproducts form)OHBFFFHH:B3 pts each mechanistic step (all arrows correct or no points)2 pts each intermediateGrading stops with the first impossible chemical change232 pts3 ptsName _______________________Page 2II. (41 points)A.C.SofosbuvirSofosbuvir has been marketed since 2013; since that time this drug has seen the highest cure rate and the lowest incidence of side effects for the treatment of hepatitis C.18(S)(S)OOHNPO(R)(R)(R)(R)(R)(R)F(R)(R)ONNHOOHOOO(Z)RSZOOHNPOFONNHOOHOOOFNO1O2Chybridization electronic geometry observable geometryatom O1atom O2atom N333sp2sp3sp2trigonal planartetrahedraltrigonal planarbenttrigonal planarbentall three answers must be right for the row = 2 no partialatom F3sp3tetrahedral noneatom C3sp3tetrahedral tetrahedral(c) For each of the atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic geometry (VSEPR) and observable geometry (write none if it is not observable).(a) CIrcle all the tetrahedral (chiral) stereocenters in Sofosbuvir and assign an appropriate (R or S) stereolabel.(b) Label the double bond that is indicated with the arrow and the box.SofosbuvirConvert name to structure or structure to name as needed. Be sure to include all information on connectivity and stereochemistry in both your drawings and your naming.-if wrong connectivity: 0-if stereo is wrong but connectivity is right: 2(a) Name this compound:(b) Draw this compound:OH44-2 pts/ error up to 4may be 3S, 6E, S and E can be in either order(S,E)-6-methyloct-6-en-3-olBr(R)-1-bromo-4,5-dimethylcyclohexa-1,3-dieneRRRName _______________________Page 3III. (40 points)One Both NeitherWhich of these products is/are optically active? (check one)Xenantiomersdiastereomersstructural isomersThese products are (check one):XH2SO4 (cat.)422A.OOOIn this set of reaction predictions, it has already been determined that two different (but related) neutral organic products form (please ignore byproducts). Draw both products, clearly showing in your drawing all structural and/or stereochemical information that distinguishes them from each other. Then discuss the optical activity of these products and their relationship.HOKMnO4H2O (excess)H2SO4 (cat.)CH3OHOne Both NeitherWhich of these products is/are optically active? (check one)Xenantiomersdiastereomersstructural isomersThese products are (check one):X422One Both NeitherWhich of these products is/are optically active? (check one)Xenantiomersdiastereomersstructural isomersThese products are (check one):X422One Both NeitherWhich of these products is/are optically active? (check one)Xenantiomersdiastereomersstructural isomersThese products are (check one):X422One Both NeitherWhich of these products is/are optically active? (check one)Xenantiomersdiastereomersstructural isomersThese products are (check one):X422OH(S)(S)(S)(S)(R)(R)(R)(R)HOHOOHOH(R)(R)(S)(S)(R)(R)(S)(S)HOHOOHOHNew OH s must be syn1) BH32) H2O2/NaOHOHOHOHHOOHHOmust show the cis and transClOCH3OCH3must have correct products to receive credit for analysismust have correct products to receive credit for analysis(HBr) not neededB.C.D.E.1 equiv.Name _______________________Page 4IV. (43 points)CH3SeLiClClSeCH3δδHNHNHCH3(a) Provide an accurate and complete three-dimensional orbital picture for Compound 3, considering all major resonance contributors when making your assessments about geometry. You should use lines, dashes, wedges, and p orbitals (lone or overlapping) to show the direction of all electrons (or empty orbitals) in your drawing. All bond angles should reflect the appropriate geometry and hybridization chosen for your drawing.CNHNHHCHHH3 pts/atomp orbital must be consistent with hybrid planeif a different contributor is shown, charges will be presentHNHNHCH3Compound 3BF3HNHNHCH3BF3Compound 3HNHNHCH3HHBr(b) Balance the following reactions, each involving Compound 3.BrA.B.(i)(ii)Provide all requested information.(i) a single chiral product forms; draw it(a)(ii) draw the transition state for the single mechanistic stepH3CSe(b)SeCl2 is a strong electrophile that can be used in addtion reactions. This reaction proceeds with a seleniranium intermediate (analogous to a halonium ion); the electrophilic atom is easily predicted based on the dipole of the Se-Cl bond. Draw the curved arrow mechanism for the two-step reaction that produces the product shown, and answer whether other products are expected.SeClCl44Cl4412Se ClClSeClClThis product forms(check one):alonewith its enantiomerwith its diastereomer11X3 pts intermediate3 pts each step2 pts with stereoanswer(c) Selenium electrophiles like SeCl2 form products that display Markovnikov regioselectivity. Use this information and the information above to predict the product(s) for this reaction. If the product forms as a stereoisomeric mixture, draw one clearly and write "+ enantiomer" or "+ diastereomer" to indicate the other product.ClClSeClSeCl2+ diastereomer4Name _______________________Page 5V. (38 points)the same molecule structural isomers


View Full Document
Loading Unlocking...
Login

Join to view Key 5 and access 3M+ class-specific study document.

or
We will never post anything without your permission.
Don't have an account?
Sign Up

Join to view Key 5 and access 3M+ class-specific study document.

or

By creating an account you agree to our Privacy Policy and Terms Of Use

Already a member?