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This document is a practice exam for an organic chemistry course. It contains multiple choice and open response questions testing concepts related to organic nomenclature, reactions, spectroscopy, and mechanisms. The exam covers topics such as functional group interconversions, addition and elimination reactions, stereochemistry, polymerization, and resonance structures. It provides NMR spectra, IR spectra, and reaction schemes for students to analyze and answer questions about identifying compounds and predicting reaction outcomes.
This document is a practice exam for an organic chemistry course. It contains multiple choice and open response questions testing concepts related to organic nomenclature, reactions, spectroscopy, and mechanisms. The exam covers topics such as functional group interconversions, addition and elimination reactions, stereochemistry, polymerization, and resonance structures. It provides NMR spectra, IR spectra, and reaction schemes for students to analyze and answer questions about identifying compounds and predicting reaction outcomes.
This document is a practice exam for an organic chemistry course. It contains multiple choice and open response questions testing concepts related to organic nomenclature, reactions, spectroscopy, and mechanisms. The exam covers topics such as functional group interconversions, addition and elimination reactions, stereochemistry, polymerization, and resonance structures. It provides NMR spectra, IR spectra, and reaction schemes for students to analyze and answer questions about identifying compounds and predicting reaction outcomes.
I. Multiple Choice I (13 questions, 2 pts each, 26 pts overall)
1. The IUPAC name for diisobutylacetylene is A) 2,7-Dimethyl-4-octene B) 2,7-Dimethyl-4-octyne C) 3,6-Dimethyl-4-octyne D) 2,5-Diethyl-3-hexyne E) 2,2,5,5-Tetramethyl-3-hexyne
2. Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is incorrect to state that: A) it favors E2 reactions over competing S N 2 reactions. B) it will form, predominantly, the more stable alkene. C) it tends to give the anti-Zaitsev, i.e., Hofmann, product. D) it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol. E) this base is more effective than ethoxide ion, because it (KO-t-Bu) is the more basic of the two.
3. What is the major product of the reaction:
A) I B) II C) III D) IV E) Both III and IV
i) BH 3 , THF ii) H 2 O 2 ,NaOH CH 3 CH 3 OH OH CH 3 I II III IV CH 3 OH ? + enantiomer + enantiomer
Page 2 4. Which reaction sequence would convert cis-2-butene to trans-2-butene? A) Br 2 /CCl 4 ; then 2 NaNH 2 ; then H 2 /Ni 2 B(P-2) B) Br 2 /CCl 4 ; then 2 NaNH 2 ; then Li/liq. NH 3
C) H 3 O + , heat; then cold dilute KMnO 4
D) HBr; then NaNH 2 ; then H 2 , Pt E) None of these
5. Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would: A) be a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial. B) be a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial. C) be a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial. D) be a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. E) be a pair of diastereomers and, in their most stable conformation, one would have the bromines equatorial and axial, and the other would have the bromines equatorial and equatorial.
6. Compound X has the molecular formula C 6 H 10 . X decolorizes bromine in carbon tetrachloride. X also shows IR absorption at about 3300 cm -1 . When treated with excess hydrogen and a nickel catalyst, X yields 2-methylpentane. The most likely structure for X is: A)
B)
C)
D)
E)
Page 3 7. Which of the following species is not a resonance form of the following species?
A)
B)
C)
D)
E)
8. Which statement is/are true about alkynide anions? A) They are weak bases and weak nucleophiles. B) The carbon atom that bears a negative charge is sp 3 hybridized. C) With a tertiary alkyl halide, an alkynide anion will act as a nucleophile to produce high yield of an alkylation product. D) All of the statements are true. E) None of the above is true.
9. Which of these dienes can undergo the Diels-Alder reaction? A)
B)
C)
D)
E) All of the above can undergo the Diels-Alder reaction.
O O O O O O
Page 4 10. Free radicals can be produced by: A) use of high temperatures. B) irradiation with light. C) reaction of a molecule with another free radical. D) both A) and B). E) all of A), B) and C).
11. Which of the reactions listed below would be exothermic? A) CH 3 CH 3 2CH 3
B) CH 3 + CH 4 CH 4 + CH 3
C) 2(CH 3 ) 2 CH (CH 3 ) 2 CHCH(CH 3 ) 2
D) H + (CH 3 ) 3 CH (CH 3 ) 3 CH + H E) None of the above
12. Which would be the best synthesis?
A)
B)
C)
D)
E)
13. The reaction of 1-butene with HBr in the presence of peroxides yields 1-bromobutane. The mechanism for the reaction involves: A) attack on the alkene by a Br + ion. B) attack on the alkene by a H + ion. C) attack on the alkene by a bromine atom, Br. D) attack on the alkene by a hydrogen atom, H. E) isomerization of the 2-bromobutane produced initially.
What is the structure of the compound in the following 1 H-NMR spectrum with the molecular formula C 6 H 12 ? Relative integration is shown.
A)
B)
C)
D)
E)
0 1 2 3 4 5 6 7 8 PPM 2 1 3 6
Page 6 III. Spectroscopy (8 pts) An unknown compound, Y, has the formula C 6 H 4 Cl 2 O. Elucidate the structure of Y by scrutinizing its IR, 1 H NMR and 13 C NMR spectra, shown below.
Note: the triplet in the 13 C NMR spectrum at 82 ppm is due to the solvent, CDCl 3
Page 7 IV. Reactions (14 pts)
A. (10 pts) Draw the major product(s) after each arrow in the following reactions. Clearly depict stereochemistry where appropriate.
B. (4 pts) Provide reagents for the following transformations.
Br CH 3 O + CO 2
Page 8 V. Mechanisms (14 pts) Provide a detailed mechanism (with electron flow arrows) for the following reactions. Clearly show the final product formed. (If you cannot predict the mechanism, there will be partial credit for showing correct products). If several products may form, only show the major one.
a) (6 pts) H 2 C=C(CH 3 ) 2 + HF
b) (8 pts) Radical polymerization of CH 3 CH=CH 2 initiated by peroxide H 2 O 2
Page 9 VI. Radical Reactions (10 pts)
Using bond dissociation energies, calculate the heats of the two possible reactions of the isopropyl radical, (CH 3 ) 2 CH with HBr leading to the abstraction of either H or Br atom. Draw the energy diagram for these two reactions. Which of them is more likely to occur?
Page 10 VII. Synthesis and Nomenclature (12 pts)
a) (6 pts) Propose a method for the stereoselective synthesis of the following molecule. from HO OH (racemic) and Cl CO 3 H and any inorganic reagents
a) (3 pts) Propose a one-step method for the stereoselective synthesis of the following molecule.
F F starting from molecules with four carbon atoms or less
b) (3 pts) Name this molecule using the R,S system and IUPAC nomenclature.
F F
Page 11 VIII. Open Response (12 pts)
1. (2 pts) Draw the structure of (Z)-1-bromo-2-chloropropene
2. (2 pts) What monomer should be used to prepare -(CH 2 -CH=CH-CH 2 ) n -?
3. (2 pts) Give one example of a catalyst that can be used for the hydrogenation of alkynes to alkanes.
4. (2 pts) How will the reaction products of the addition of HCl to propene differ in the absence and presence of peroxides?
5. (2 pts) What simple text can be done to distinguish between 1,3-pentadiene and 1,4-pentadiene, other than running a proton NMR spectrum?
6. (2 pts) Draw two resonance structures for the allyl cation. Show all carbon and hydrogen atoms.