Final 2009 (answers)

Final 2009 (answers) - Fall 2009 Chern 2 66 2 1. For the...

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2 Fall 2009 Chern 266 1. For the following compound, the hybridizations of the atoms labeled i and ii are best described as: A) i, sp; ii, sp iii B) i, sp; ii, Sp2 H 3 C-N=N-O-C=N C) i, Sp2; ii, Sp2 G i, Sp2; ii, sp Sf 8-. .- S P E) i, Sp3; ii, sp 2. Which ofthe following compounds contains a quaternary carbon atom and a secondary alcohol? OH A B E 3. In each of the following molecules two protons have been labeled. Which hydrogen is the most acidic in each molecule? iii H A) i and iii .. B) i and iv .9. ii and iii ~iiandiv 4. Of the following compounds, interconversion between two chairs of equal energy is only Ckl3 possible in the case of H~Q'f., ~ trons-l,3-cyclohexanediol -::;: ~ _ t...- B) trans-l,2-dimethylcyclohexane~ HO ~ H -0 I 011 to X c...rt C) ethylcyclohexane :x R'f,. f1 ~ 1. D) 1,2-diethylbenzene K E) trans-4-tert-butylcyclohexanol )( S. In the following reaction, the fastest reaction rate will be observed when X is: ~OCH3 + NaX A) Br B) CI C) F 0) OH E) , ~ 1. ~ bes 1- I ~(AV \~.5 9\r~ \}J ~\<.4-S}- b (1 S
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~ Fall 2009 Chern 266 3 6. In the following reaction two major substitution products are formed. W,hPf relationship do ~ they have with each other? ~'" - ~~ '(Y l\ A) enantiomers /\ J (J r6> & diastereomers ~OH ~ (£) e S ,.II C) constitutional isomers U HBr .. ~ \3r D) structural isomers ~ 6,. ~~' E) optical isomers W 1"" '--" 7. Which of the following compounds would be called a meso compound? (l-ot- ~.Jd·tdl ? HoTOH ii eOOH ~ - H-t-0H eOOH Iv A) i and iii only B) i, ii and iii only tf) i, iii and iv only D) ii and iii only E) iii only 8. Which of the proposed reagents would be the best way to carry out the transformation below? A) NaBH 4 /EtOH then HBr B) NaBH 4 /EtOH then Br2 C) pyridinium chlorochromate then HBr (DI LiAIH 4 then H 2 0 then PBr3 E) LiAIH 4 then H 2 0 then NaBr 9. What is the major product of the following reaction?
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. For the following compounds, the order of decreasing Bn~nsted acidity (from most acidic to least acidic) is: E otE:) 6 D iii olE? C Chern 266 orS) 2. H 3 0+ 3. cat. H 2 S0 4 in EtOH A (.) t'NIj f!-r. Ph~OC-H.3~ What is the major product of the following reaction? CH~ :;) d.-t!~ ~\L-e. .. s- cf~ ~ 0- 1. CH 3 MgBr (excess), ether Fal12009 10. 11. CA) ii > iii > i > iv D) i > ii > iii> iv C) i > iii > ii > iv B) iv > iii > ii > I E) i > iv > iii > ii 12. Each of the following reactions will give an alcohol as one of the major products. i) These alcohols are best classified as: ii) iii) iv) A) i, primary; ii, secondary; iii, primary; iv, secondary B) i, primary; ii, primary; iii, secondary; iv, secondary C) i, primary; ii, secondary; iii, secondary; iv, primary @) i, primary; ii, primary; iii, secondary; iv, primary E) i, secondary; ii, secondary; iii, secondary; iv, primary
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5 Fall 2009 Ch·em 266 13. For each of the following reactions, how is the stereochemistry at the carbon labeled with
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This note was uploaded on 10/21/2010 for the course CHEM 266 taught by Professor Pols during the Fall '07 term at Waterloo.

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Final 2009 (answers) - Fall 2009 Chern 2 66 2 1. For the...

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