Spring03Test1 - NAME SS# Introductory Organic Chemistry...

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Unformatted text preview: NAME SS# Introductory Organic Chemistry 030.104 (ow. 2953 MIDTERM EXAM #1 March 6, 2003 Dr. Kleln - Circle Your TA’s Name Castaldo, Lyana Dunks, Jill Gunsior', Michelle 2 _ 3 - 4 _ 5 - 6 - Hill, Eric - Kapur, Pram Liu, Yonglin Shah, Meha “- u- _ - - Weather-wax, Anthony _ - - - - 1) For each labeled carbon atom in the molecule below, identify the number of H’s attached, the hybridization state and the geometry: (1 pt each) # of H's attached # of H's attached a) hybridization state hybridization state geometry geometry # of H's attached __ # of H5 attached b) hybridization state __ e) hybridization state geometry _______.___ geometry # of H's attached __ # of H's attached __ C) hybridization state hybridization state geometry geometry 2) Identify the formal charge in each of the following cases: (2 pts each) a) b) /N¢N . 3) a) Using the carbon atoms belOw,‘ show (with drawings) how atomic orbitals overlap to give a sigma bond or a pi bond: (2 pts each) SIGMA PI b) Sigma bonds are free to rotate, but pi bonds are not free to rotate. Explain why based on your drawings above. Limit your answer to one sentence (points will be deducted for unnecessary rambling on). (2 pts) 4) Name the following compounds: (5 pts each) NAME CI Cl 5) Using Newman projections, draw the most stable conformation and the least stable conformation of butane: (2 pts each) MOST STABLE LEAST STABLE 6) Draw resonance structures for the following compounds (show the curved arrows): (2 pts each) 7) Consider the compound below: a) Draw both chair conformations of this compound. (2 pts each) b) Circle the chair conformation that is more stable. (1 pt) c) Explain your choice in one sentence or less. (2 pts) 8) In each case, circle the anion that is more stable. Then, explain why using ONLY ONE WORD (i.e. which of the four factors that we discussed in class can be used to explain your choice). (2 pts each) A k a) FACTOR A ' b) 9 VS' 41* FACTOR A E c) 9 VS' 0' 9 0' FACTOR A ~ . N d) 9 VS \9 FACTOR 9) Consider the three protons shown in the following compound. Circle the most acidic proton. (2 pts) 10) Show the mechanism (curved arrows) for the following acid-base reaction: (4 pts) /U\O/H + =— + H20 11) Tertiary carbocations are more stable than secondary carbocations, which are more stable than primary carbocations. One important reason for this trend is “hyperconjugation”. Hyperconjugation helps us understand why alkyl groups are electron donating. Draw a picture that shows what hyperconjugation is: (3 pts) 12) Show the mechanism (curved arrows) for the initiation step of a free-radical chlorination. (2 pts) 13) Identify all of the stereocenters in the following molecules (circle the carbon atoms that are stereocenters), and assign the configuration of each one (label each one as either R or S): (10 pts) CI/,,.©§/Vo\/\ H OH é H0:i:H _ Me 14) Draw the enantiomer of the following compound: (2 pts) Et v0“ 15) For each of the following pairs of compounds, determine whether the compounds are enantiomers, diastereomers, or the same compound: (2 pts each) Me Me H —*-Cl CI H HO——H HO H Me Me Relationship NOH OOH Relationship . 25 0 Relationship EXTRA CREDIT (1 pt) Compound A has a pKa of 5. Compound B has a pKa of 9. Compound A is times more acidic than compound B. ...
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This note was uploaded on 04/07/2008 for the course CHEM 205 taught by Professor Klein during the Spring '03 term at Johns Hopkins.

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Spring03Test1 - NAME SS# Introductory Organic Chemistry...

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