PS1 Solutions - Name Section Rec TA Side 1 of 9 Ch 1b...

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Name Ch 1b, Problem Set One Section Side 1 of 9 Due Friday, Jan. 7, 2011 Rec TA at 4 PM PST in the Drop Box 1. Molecular Hybridization ( 15 points ) Below, the chromophore of neocarzinostatin is shown. This enediyne molecule, in conjunction with its apoprotein partner, has been shown to exhibit anticancer activity. For the numbered atoms, provide the hybridization state of the atom (e.g. sp, sp 2 , etc.). SOLUTION (1 pt. each) 1. sp 2 2. sp 2 3. sp 3 4. sp 3 5. sp 3 6. sp 7. sp 8. sp 2 9. sp 3 10. sp 2 11. sp 3 12. sp 3 13. sp 3 14. sp 3 15. sp 3 2. Assigning IUPAC Names for Hydrocarbon Structures ( 8 points ) Provide the IUPAC name for each of the following structures. Do not include cis- and trans- designations for molecules containing double bonds. SOLUTION (2 pts. each: 1 pt. for carbon chain, 1 pt. for numbering – give partial credit where possible ) a. 4-ethyl-3-methylheptane b. 4-methylcyclohexene OR 4-methyl-1-cyclohexene c. 4-isopropyl-2-heptyne OR 4-methylethyl-2-heptyne OR 4-(1-methylethyl)-2-heptyne d. 4- tert -butyl-3-heptene OR 4-dimethylethyl-2-heptene OR 4-(1,1-dimethylethyl)-2-heptene
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Name Ch 1b, Problem Set One Section Side 2 of 9 Due Friday, Jan. 7, 2011 Rec TA at 4 PM PST in the Drop Box 3. Assigning IUPAC Names for Structures with Functional Groups ( 12 points ) Provide the IUPAC name for each of the following structures. Do not include cis- or trans- designations. SOLUTION ( 3 pts. each: 1 pt. for functional groups, 1 pt. for carbon chain names, 1 pt. for numbering – give partial credit where possible ) a. 2-pentyn-1-ol b. 1-chloro-3-ethoxypropane c. 3-bromo-1-chloro-2-butene d. 4-heptyn-3-one e. 2,2,2-trichloroacetaldehyde OR 2,2,2-trichloroethanal NOTE: Accept answers without 2,2,2- since there is no ambiguity f. m -bromobenzoic acid OR 3-bromobenzoic acid
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Name Ch 1b, Problem Set One Section Side 3 of 9 Due Friday, Jan. 7, 2011 Rec TA at 4 PM PST in the Drop Box 4. Structural Isomers and Stereoisomers ( 12 points ) Draw structures of all of the structural isomers and stereoisomers that are possible for C 3 H 5 Cl 3 . Name each one. For enantiomers, you do not need to specify the configuration in the name (e.g., R/S, d/l, +/-). However, you should draw stereoisomers using the wedge/dash formalism in order to convey the proper relationships between atoms at stereocenters.
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