1. What is the hybridization of the indicated atom in the following molecule?
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1 Practice Final Exam, Chemistry 2210, rganic Chem I 1. What is the hybridization of the indicated atom in the following molecule? A. sp 3 B. sp 2 C. sp D. not hybridized 2. Name the functional groups in the following molecule (in order from left to right). N A. Secondary alcohol, ketone, secondary amine, ether B. Primary alcohol, ketone, secondary amine, ester C. Secondary alcohol, amide, ketone, ether D. Primary alcohol, amide, ester 3. Which of the following is the strongest acid? A. B. C. D. N 2
2 4. Give the IUPAC name of: A. trans-1-neopentyl-2-cyclohexanol B. cis-2-tert-butylcyclohexanol C. trans-2-tert-butylcyclohexanol D. cis-2-sec-butylcyclohexanol 5. Give the IUPAC name of: Cl 3 C Cl Cl C 3 A. (2R,3R,4S)-3,3,4-trichloro-2-pentanol B. (1R,3S)-2,2,3-trichloro1,4-dimethyl-1-butanol C. (2R,4R)-3,3,4-trichloro-2-pentanol D. (2R,4S)-3,3,4-trichloro-2-pentanol 6. Which of the following is true about this reaction? Cl Br DMS A. The product will have R configuration. B. A racemic mixture is produced. C. The product will have S configuration. D. The product is not optically active.
3 7. What is the IUPAC name of this compound? A. cis-2,3-dimethyl-3-hexene B. trans-2,3-dimethyl-3-hexene C. (Z)-2,3-dimethyl-3-hexene D. (E)-2,3-dimethyl-3-hexene 8. What will be the major organic product of the following reaction? K heat Br A. B. C. D. 9. What is the major product of the following reaction?
4 10. Which of the following compounds would produce both of these ketones in an ozonolysis reaction? and A. B. C. D. 11. Which of the following is the least stable radical? 12. Which of the following reactions would form 1-bromo-3-methyl butane from 3-methyl-1- butene? A. Reaction with Br B. Reaction with Br in presence of peroxides C. Reaction with NBS in presence of light D. Reaction with Br 2 in presence of light
5 13. Arrange these hydrogens by aciditity, most acidic first. d b C 2 c a A. c > d > b > a B. a > c >d > b C. c > b > d > a D. a > c > b > d 14. Which structure has the IUPAC name: 7-tert-butylbicyclo[4.3.1]decane. A. B. C. D. 15. Which conformer has torsional strain and steric strain? A. C 3 C 3 B. C 3 C 3 C. C 3 C 3 D. C 3 C Which description is correct for the following compound? A. Achiral B. Meso C. ptical active D. It is not superimposable on its mirror image
6 17. Which one is the best synthetic route to obtain the following compound? A. B. C. D. 18. What is the product of the following reaction? Br NaC 3 C 3 A. B. and C. D. and
7 19. Which one is the correct set of reagents/conditions to carry out the following reaction? A. g(ac) 2, 2, then NaB 4 B. B 3 TF, then 2 2 / - C. 3 +, 2, heat D. Cold KMn 4, 2, Which would be the best way to carry out the following synthesis? A. (1) Br 2 /heat; (2) (C 3 ) 3 CK/(C 3 ) 3 C; (3) cold KMn 4, 2, - B. (1) Br 2 /heat; (2) K/C 3 ; (3) cold KMn 4, 2, - C. (1) Br 2 /CCl 4 ; (2) (C 3 ) 3 CK/(C 3 ) 3 C; (3) C 6 5 C; 3 + D. (1) Br 2 /CCl 4 (2) K/C 3 /(C 3 ) 3 C; (3) C 6 5 C; In the molecule shown below, please arrange by bond dissociation energy, largest BDE first. A. a > c > b > d B. a > c > d > b C. c > a > d > b D. c > a > b > d 22. Which is the major product? A. B. C. D.
8 23. Which is the major product? A. B. C. D. 24. Which reagent(s) are most suitable to accomplish the following reaction: A. N 3 then ethyl bromide B. Ethyl bromide then N 3 C. NaN 2 then ethyl bromide D. Ethyl bromide then NaN Which base/ conjugate acid pair is correct 26. Which carbocation is likely to undergo a 1,2 hydride shift?
9 27. Name the following compound (IUPAC rules): A. (S,E)-hex-2-en-4-ol B. (R,E)-hex-4-en-2-ol C. (R,Z)-hex-2-en-4-ol D. (S,E)-hex-4-en-2-ol 28. Which of the following reactions would most likely occur via an S N 1 pathway? 29. For the C 2 molecule, what is the shape, bond angle, and hybridization of the carbon atom? A. Bent, 109, sp 2 B. Bent, 120, sp 3 C. Linear, 180, sp D. Pyramidal, 120, sp Which reaction favors formation of the products?
10 31. The compound which best fits the IR spectrum below is: A. C 6 5 N 2 B. C 3 C 2 C. C 3 C 2 C 2 C 3 D. C 3 C First, identify the compound with the highest boiling point. What is its Index of ydrogen Deficiency? A. 0 B. 0.5 C. 1 D ow many tetrahedral stereocenters (asymmetric carbons; chirality centers) does the following molecule have? A. 3 B. 2 C. 1 D. 0
11 34. Consider the following reaction and kinetic data and deduce the mechanism of the reaction from this information: [RBr] [Na] relative rate A. S N 1 B. S N 2 C. E1 D. E2 35. The alkene that forms in the following alcohol dehydration reaction as the major product is: A. tetrasubstituted B. trisubstituted C. disubstituted D. monosubstituted 36. Which of the following is the best synthesis for 2,2-dibromopentane? A. Addition of Br 2 in CCl 4 to 1-pentene. B. Bromination of pentane using excess of Br 2 in the presence of light. C. Addition of Br to 1-pentyne in the presence of peroxides. D. Addition of Br to 1-pentyne. 37. ow many bonds in this molecule are formed by an s-sp 3 overlap? 2 N A. 4 B. 5 C. 6 D. 7
12 38. Rank the following bases in order of increasing base strength (weakest base first) A. II<III<I<IV B. II<III<IV<I C. II<I<III<IV D. II<I<IV<III 39. What are the products of the reaction shown below? C 3 C CNa + C 3? A. 3CC C + NaC 3 B. C 3C CC 3 + Na C. D. C 3C CC 3 + Na 40. When the following 4 alkenes are combusted, which would give off the least heat? A. (C 3 ) 2 C=CC 2 C 3 B. C 3 C=CC(C 3 ) 2 C. (C 3 ) 2 C=C(C 3 ) 2 D. C 2 =C(C 3 )C 2 C 2 C Which reaction sequence would convert cis-2-butene to trans-2-butene? A. Br 2 /CCl 4 ; then 2 NaN 2 ; then 2 /Ni 2 B B. Br 2 /CCl 4 ; then 2 NaN 2 ; then Li/N 3 C. 3 +, heat; then cold dilute KMn 4, - D. Br; than NaN 2; then 2 /Pt
13 42. What is the major product? 1) g(ac) 2, TF, 2 2) NaB 4, - A B C D 43. The free radical chlorination of 2,2-dimethylbutane produces this number of monochlorinated products, including stereoisomers A. 2 B. 3 C. 4 D Which of the following is a propagation step in the chlorination of methane? A. Cl-Cl 2 Cl B. Cl + C 4 C 3 + Cl C. C CCl C 4 + C 2 Cl D. C 3 + C 3 C 3 C Determine formal charges of boron and oxygen in the following structure. Lone pairs are not shown, so use the octet rule to determine where they are: F C F B F C A. B = +1; = + 1 B. B = -1; = - 1 C. B = +1; = - 1 D. B = -1; = + 1
14 46. What is wrong with the mechanistic arrow shown here? A. It should start on the alkyne carbon. B. It should start on a hydrogen attached to the nitrogen. C. It should start on an unshared pair on nitrogen, end at the on the alkyne, and a second arrow should start at the bond between the C and on the alkyne and end on the terminal carbon of the alkyne. D. There should be two arrows-one from nitrogen and from the alkyne carbon. 47. What is the IUPAC name for the following compound? C 3 Cl A. (R)-6-chloroheptane B. (S)-3-chloroheptane C. (R)-1-chloro-2-methylhexane D. (S)-6-chloro-5-methylhexane 48. Pure (S)-bromobutane has a specific rotation of o. If you have a mixture of R and S enantiomers and this mixture rotates light by -6.0, then what is the composition of your mixture. (What is the percent of R and what is the percent of S in the mixture?) A. 60% R and 40% S B. 40% R and 60% S C. 47% S and 53% R D. 47%R and 53% S
15 49. Which of the following compounds is the same as compound I? I II III IV A. II B. III C. IV D. III and IV 50. Rank the following substrates from most to least reactive in an S N 2 reaction. I. II. III. IV. A. I>II>III>IV B. IV>I>II>III C. II>III>I>IV D. III>II>I>IV
Final Examination, Organic Chemistry 1 (CHEM 2210) December 2000 Version *A* A. B. C. D.
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