Chem 241 Fall Practice Problems For Chapters 1-4
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1 Chem all 008 Practice Problems or Chapters - Question. itrate ( ) is a common inorganic anion that you have encountered in general chemistry. The structure of the nitrate anion is shown below: verall charge: n the structure above, draw in the nonbonding valence electrons for each atom. n the structure above, provide formal charges for each atom that bears a formal charge. What is the hybridization state of the nitrogen atom? d) Draw two additional resonance structures for the nitrate anion. sp e) Draw a resonance structure for the nitrate anion that has a positive charge on one of the oxygen atoms (it is K if this is a duplicate structure from part d). Is this a "major" or "minor" resonance form? Provide two justifications for your answer. This is a "minor" resonance structure. The positively-charged oxygen atom does not have a full octet.. xygen is electronegative (.0) and does not easily support a positive charge. f) Although nitrate appears to have one double bond and two single bonds, all three bonds are actually the same length. Explain.
2 Chem all 008 The above resonance structures, when combined, give an accurate depiction of the nitrate anion. A more accurate single structure is shown below: / of a double bond / / / Question. Translate the following ewman projections into Lewis structures (line structures are K). C Et C C 6 C Et Question. Translate the following compounds into staggered ewman projections.,-dichloroethane or Et Et or or The conforational isomers in boxes for parts a and b above are the lowest energy conformations. Why might this be? (Part c is much more complicated)
3 Chem all 008 Question. The chemical structure for vitamin A, a highly unsaturated hydrocarbon (with one oxygen atom) is shown below. Use this structure to answer the following questions. C C C C C Vitamin A ow many degrees of unsaturation are there in vitamin A? one ring and 5 double bonds = six degrees of unsaturation ow many atoms are sp -hybridized? total: carbon atoms and one oxygen atom 7 8 C C C C 9 0 C 5 6 ow many atoms are sp -hybridized? 0 total: all carbon atoms C C C C 9 0 C d) ow many atoms are sp-hybridized? none e) Label each double bond in vitamin A as (E), (Z), or "not applicable."
4 Chem all 008 C C C C E E E E Z C Question 5. or each compound below, briefly describe why the structure is unstable or cannot exist. Triple bonds are only stable in rings of 8 carbons or greater The central carbon atom has 5 bonds (impossible) This structure diobeys edt's Rule d) C C The circled carbon has 6 bonds (impossible)
5 Chem all 008 Question 6. or the following pairs of compounds, circle the molecule that is more stable. Increased olefin substitution This structure disobeys edt's Rule Increased olefin substitution Question 7. Label each of the following molecules as chiral or achiral. a. C chiral b. C achiral c. -methylheptane achiral d. -methylheptane chiral e. -methylheptane achiral f. cis--butene achiral g. trans--butene achiral h. cis-,-dimethylcyclobutane achiral i. trans-,-dimethylcyclobutane chiral 5
6 Chem all 008 Question 8. Assign the stereochemistry (R or S) for each stereocenter in the following molecules. o, you do not have to fully name the compounds. S R C C S R Question 9. The common non-steroidal analgesic, ibuprofen, has the structure shown below. C ibuprofen ow many degrees of unsaturation does ibuprofen have? ive. our double bonds and one ring 6
7 Chem all 008 nly the (S)-enantiomer of ibuprofen helps relieve pain. Draw the (S)- enantiomer of ibuprofen. C Question 0. The following compound is a bit of an oddity. Is it chiral or achiral? ow many stereocenters does it contain? Does it have an internal mirror plane? Does this change our "rules" for chirality at all? * This molecule is achiral (mirror images are superimposable) It contains zero stereocenters (wierd - I know) It does not have a mirror plane but it does contain a type of symmetry. It contains a point of inversion (all aspects of the molecule are reflected through this point - marked with a *). Molecules with points of inversion are rare. This does not change our rules for chirality - whether a molecule is or is not superimposable with its mirror image. But some "strange" molecules may force us to look very closesly! 7
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