Organic Chemistry I. Summer Final Exam

Transcription

1 Print Name: rganic hemistry Summer 2014 Final Exam SPEAL NSTRUTNS: Please make sure to read each questions VERY carefully!! Some questions will look similar to questions on previous tests, but contain slight alterations that could completely change the question!!! onor ode: Students must abide by the Tennessee Wesleyan onor System. You have pledged, on your honor, to conduct yourself with the foremost level of academic integrity. As such, you must sign the certification below: exam. hereby certify that have neither given nor received unauthorized aid on this Student Signature

2 Multiple hoice (2 points each) 1) What is the major product for the following reaction? A) B) ) ) E) 2) redit for the first synthesis of an organic compound from an inorganic precursor is usually given to. a) Berzelius b) Arrhenius c) Kekule d) Wohler e) Lewis 3) The UPA name for is: a) 6-Ethyl-3,4-dimethylheptane b) 2-Ethyl-4,5-dimethylheptane c) 3,4,6-Trimethyloctane d) 3,5,6-Trimethyloctane e) 2-(1-Methylpropyl)-4-methylhexane 4)What is the major product for the following reaction? A) B) ) ) E) More than one of these choices.

3 5) Which of the following compounds (-V) represent enantiomers? V A) and B) and ) and V ) and V E) and 6) Select the most electronegative element from the list below. a) b) c) N d) B e) 7) What is the major product of the following reaction sequence? 1. t-buk, t-bu 2. A) B) ) ) E) None of these choices. 8) Rank the following hydrogen atoms from highest to lowest in acidity in the structure shown below. a) a>b>c>d b) a>c>d>b c) c>d>a>b d) d>a>c>b e) c>a>d>b 9) Name the following compound: 3 A) (cis)-3-methoxyhex-3-ene B) (Z)-4-methoxyhex-4-ene ) (Z)-3-methoxyhex-3-ene ) (E)-3-methoxyhex-3-ene E) 3-methoxyhex-3-ene

4 10) What is the major product for the following reaction? a. g(ac) 2, 2 b. NaB 4, Na A) B) ) ) E) More than one of these choices. 11) What functional group is present in the following compound? A) 1 o alkyl halide B) 2 o alcohol ) 2 o alkyl halide ) 1 o amine E) 3 o alkyl halide 12) The correct UPA name for the following compound is: a) 1-methyl-2-ethyl-3-cyclopropanol b) 2-methyl-3-ethyl-1-cyclopropanol c) 2-ethyl-3-methyl-1-cyclopropanol d) 1-ethyl-2-methyl-3-cyclopropanol e) none of these choices 13) What is the major product of the following reaction sequence? 1. Et, EtNa, heat 2a. B 3 :TF 2b. 2 2, Na A) B) ) ) E) An equal mixture of two of these choices. 14) The hybridization state of the charged carbon in a carbocation is. A) sp 4 B) sp 3 ) sp 2 ) sp E) s

5 15) Which compound(s) contain(s) tertiary carbon atom(s)? F V V A),, B) ), ), V E) V 16) What would be the major product of the following reaction? 2, 4? V A) Equal amounts of and. B) Equal amounts of and. ) Equal amounts of and V. ) and as major products, and V as minor products. E) All of these choices in equal amounts. 17) Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic. 3 N 3 V V a) > > > V > V b) V > V > > > c) V > > V > > d) > V > V > > e) V > V > > > 18) Which is a meso compound? A) (2R,3R) -2,3-ibromobutane B) (2R,3S) -2,3-ibromopentane ) (2R,4R) -2,4-ibromopentane ) (2R,4S) -2,4-ibromopentane E) (2R,4S) -2,4-ibromohexane Ph

6 19) What is the major product of the following reaction sequence? 1. 2, 4 2a. NaN 2 (excess), N 3 2b. 3 + A) B) ) ) E) More than one of these choices. 20) According to the Lewis definition, a base is a(n). a) proton donor b) electron pair donor c) hydroxide ion donor d) hydrogen ion donor e) electron pair acceptor 21) The most stable conformation of 3-bromo-2-methylpentane, viewed through the -3-4 bond (i.e., -3 in the front, -4 in the back): 3 ( 3 ) 2 ( 3 ) 2 3 ( 3 ) ( 3 ) 2 V V a) b) c) d) V e) V 22) What are the major product(s) formed by treating 1,2-dimethyl-1-cyclopentene with 2? A), B), ) V, V ), E) None of these choices.

7 23) Which is the weakest nucleophile in polar aprotic solvents? A) - B) - ) - ) F - E) All of these choices are equally strong nucleophiles, regardless of the type of solvent used. 24) Which functional group is not contained in prostaglandin E 1? A) Ketone B) 2 alcohol ) 3 alcohol ) arboxylic acid E) Alkene 25) What would be the major product of the following reaction? 2, 2? V V A) B) ) ) V E) V 26) An acid, A, has the following thermodynamic values for its dissociation in water at 27º : = -8.0 kj mol -1 ; S = -70 J K -1 mol -1. The G for the process is: a) +29 kj mol -1 b) +13 kj mol -1 c) -6.1 kj mol -1 d) -13 kj mol -1 e) -29 kj mol -1 27) Which product (or products) would be formed in appreciable amount(s) when cis-1- bromo-2-methylcyclohexane undergoes dehydrohalogenation upon treatment with sodium ethoxide in ethanol? V A) B) ) ) V E) More than one of these choices. 28) Which reaction of an alkene proceeds with anti addition? A) ydroboration/oxidation B) omination ) xidation with cold KMn 4 ) ydrogenation E) xymercuration-demercuration

8 29) Which of the following is a set of constitutional isomers? V a) and b) and c),, and d),, and V e),, and V 30) f a solution of a compound (30.0 g/100 ml of solution) has a measured rotation of +15º in a 2.0 dm tube, the specific rotation is: A) +50 B) +25 ) +15 ) +7.5 E) ) What is the major product for the following reaction? a. KMn 4, Na, heat b. 3 + A) B) ) ) E) 32) Which would be the major product of the following reaction? 2, Ni? V V A) B) ) ) V E) V

9 33) What is the percent composition of a mixture of (S) -(+) -2-butanol,[ ] 25 = º, and (R) -(-) -2-butanol,[ ] 25 = º, with a specific rotation [ ] 25 = +6.76º? A) 75%(R) 25%(S) B) 25%(R) 75%(S) ) 50%(R) 50%(S) ) 67%(R) 33%(S) E) 33%(R) 67%(S) 34) What is the major product for the following reaction? a. 3, 2 2, -78 o b. Me 2 S A) B) ) ) E) None of these choices. 35) The molecules below are: 3 F F 3 A) constitutional isomers. B) enantiomers. ) diastereomers. ) identical. E) None of these choices. 36) The structure of the product,, of the following sequence of reactions would be: NaN 2 N 3 (l) A 3 2 B 2 Ni 2 B [P-2] A) B) ) ) E)

10 37) Select the structure of the major product formed in the following reaction. 2? V V A) B) ) ) V E) V 38) raw the resonance structures for S 4-2. nclude the correct formal charge on all atoms. Also provide the true, resonance hybrid structure. (8 pts) 39) Matching: (2 points each) Place the letter of the molecule below that is a representative of the following functional groups: 1 o Alcohol 3 o Alcohol Aldehyde 3 o Amine Ketone 2 o Alkyl halide 3 o Alkyl alide Ether Alkyne Alkene 3 A) B) 3 ) ) E) F) G) ) ) J) K) L) M) N) N N ) 3 3 N

11 40) raw the anticipated R spectrum for the following compound. For full credit, you should label peaks and identify which bond type they correspond to. (10 pts) 41) Nomenclature A. Provide the UPA name for the following compounds. (4 points each) i) ii) iii) iv)

12 B. Provide the structure of the following: (4 points) i) (3S, 4R, 5R)-5-hloro-4-methyl-1-heptyn-3-ol ii)(4r)-4-bromo-1-methyl-1-cyclopentene iii) cis-1,3-dimethylcyclohexane (most stable chair) iv) (3E)-3-bromo-6,6-dimethyl-3-octene 42) Name and explain both ways to separate enantiomers chemically. (10 points)

13 43) Reactions. Provide the products for the following reactions in the corresponding spaces below. (3 points each) N 3 a) b) c) MF Me K Li d) e) f) N 3 Pd 2 1) 3 1) g(ac) 2 / 2 g) h) i) 2) Zn / Ac 2) NaB 4 1) s 4 2) NaS 3 / 2 j) 2 S 4 2 A) B) ) ) E) F) G) ) ) J)

14 44) Mechanisms. Provide the products and the complete mechanisms for the following reactions. (5 points each) A) - B) 1) g(ac) 2, 2 2) NaB 4 ) 2 2 3

15 45) Synthesis. A) Provide a retrosynthetic pathway for the synthesis of 6-methyl-1-heptanol from 1- bromo-4-methylpentane and any compounds of 2 carbon atoms or less. (5 points) B) Provide a retrosynthetic pathway for the synthesis of 1-methyl-1,2-cyclohexandiol from 1-bromo-2-methylcyclohexane. (5 points) ) Provide a retrosynthetic pathway for the synthesis of the compound below from 2,3- dimethyl-1-cyclohexanol. (10 points)