Post on 11-May-2018
Pag 1
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
Final Exam – CHM1321-B
Date:___July 4th___________ Length:__3 hrs_____ Last Name: _______________________ Professor ___Sandro Gambarotta_________________________ First Name:________________________ Student #_______________ Seat #
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Pag 2
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
1. A correct IUPAC name for the following compound is:
OH Cl A) 4-propyl-5-chloro-3-heptanol B) 4-propyl-3-chloro-5-heptanol C) 4-(1-chloropropyl)-3-heptanol D) 5-chloro-4-propyl-3-heptanol E) 3-hydroxy-4-propyl-5-chloroheptane Ans: D
2. Which cycloalkane would you expect to have the smallest heat of combustion? Briefly and schematically explain your reasoning. Ans: cyclohexane
Pag 3
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
3. Draw and name all the constitutional isomers for the formula C5H12
Answ:
4. Which of the following molecules is achiral?
CC CH3C
H
H
CH3
Br
FClH
CO2H
OH
OHH
HHO2C
CO2H
CO2H
OHH
HHOBr
CH2CH3
CH3
HO
I II III
IV V Ans: II
n-pentane
isopentane neopentane
Pag 4
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
5. Can you identify any enantiomeric pair in the list below?:
CH2CH2CH3
H3C Cl
CH3
CH2CH2CH3
Cl CH3
CH3
I II
H
H3C Cl
CH2CH2CH3
CH2CH2CH3
H H
CH2Cl
IV V
CH2CH2CH3
H3C Cl
H
III
Ans: III, IV
6. The structures
CH3
H CH3H
CH3
H CH3
H
represent: A) a single compound. B) enantiomers. C) meso forms. D) diastereomers. E) conformational isomers. Ans: A
Pag 5
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
7. Which structure(s) represent(s) diastereomer(s) of I?
CH3OHHHHO
HO HCH3
I II
CH3OHHHHO
H OHCH3
CH3OHHOHH
H OHCH3
III IV
CH3HHOHHO
H OHCH3
V
CH3OHHOHH
HO HCH3
Ans: II and III
8. Give the proper name to the molecule below (including R,S labels if applicable)
CH2CH3ClH
CH3HCl H
CH3 : Ans: (2S,3R,4S)-2,4-Dichloro-3-methylhexane
Pag 6
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
9. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. Give the structure of the alkene :
Answ:
CH3CH2C=CCH3
CH3
CH2CH3
(cis or trans)
10. Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between pure 1-pentene and pure pentane?
A) Bromine in carbon tetrachloride B) Dilute aqueous potassium permanganate C) Concentrated sulfuric acid D) All of the above E) Answers A) and B) only
Ans: D
Pag 7
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
11. What would be the major product of the following reaction?
HCl
IV
I
Cl
Cl
II
Cl
V
Cl
III
ClCl
Ans: II
12. Which compound(s) will be formed by the reaction of Br2/CCl4 with cyclohexene ?
I II III
H
Br
HBr
H
H
BrBr
H
H
BrBr
Ans:
II and III
Pag 8
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
13. What would be the major product of the following reaction? Br2, CCl4
I
CH3BrBr
C3H7
HH
CH3BrBr
C3H7
HH
II
CH3BrH
C3H7
HBr
III
C3H7
BrH
CH3
HBr
IV
?
A) Equal amounts of I and II B) Equal amounts of II and III C) Equal amounts of III and IV D) I and II as major products, III and IV as minor products E) All of the above in equal amounts
Ans: A
14. Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?
A)
B)
C)
D)
E)
Ans: C
Pag 9
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
15. Select the structure of the major product formed from the following reaction.
Ans: IV
16. The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives, by using BD3 instead of BH3. What product would you expect from the following reaction?
Ans:
I
CH3
CH3OH
CH3
OH
CH2OH HO CH3 CH3
OH
I II III IV V
1. Hg(OOCCH3)2 THF, H2O
2. NaBH4, NaOH?
CH3
CH3DHO
H CH3DH
H CH3DBD2
H CH3OHD
H CH3BD2H
D
1. (BD3)2
2. H2O2/NaOH?
+enantiomer
I
+enantiomer
II
+enantiomer
III
+enantiomer
IV
+enantiomer
V
Pag 10
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
17. What would be the final product?
Ans:
18. Which would be the best method for converting 3,3-dimethyl-1-pentene into 3,3-dimethyl-2-pentanol?
A) H3O+, heat B) BH3:THF; then H2O2, OH- C) concd. H2SO4; then H2O, heat D) Hg(OAc)2/THF-H2O; then NaBH4,OH- E) HBr; then NaOH/H2O
Ans: D
H3CC CH2
CH3RCOOH
O
product final productCH3OH, HA
(CH3)2CCH2OH
OCH3
Pag 11
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
19. What is the product, A, that would be obtained from the following reaction sequence?
A) I B) II C) III D) IV E) V
Ans: C
CH2
O
CH2
CH3CH2MgBr H3O+C CH A
C CCH2CH3 C CCH2CH2OCH2CH3 C CCH2CH2OHCH3CH2
C CCH2CH2OCH3 C COCHCH2CH3
I II III
IV V
CH3
Pag 12
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
20. Which of the following structures would be aromatic?
A) I B) II C) III D) IV E) V
Ans: B
IVI II III V
-2
2K
KK Br Br
Pag 13
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
21. What would be the major product(s) of the following reaction?
NO2
O
I II III
NO2SO3H
O
NO2
SO3HO
NO2HO3S
OHO3S
NO2
O
IV
?H2SO4
A) I B) II C) III D) Equal amounts of IV E) Equal amounts of II and IV Ans: C
22. Which compound is an acetal?
I
O OH
III
O
O
IV
O OH
II
O OCH3
Ans: II
23. Draw the structure of the compound formed when HCl is added to a solution of pentanal in methanol? Ans: O
O
Pag 14
Faculté des sciences | Faculty of Science Département de chimie et science biomoléculaire | Department of Chemistry and Biomolecular Sciences Pavillon d’Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uOttawa.ca
24. Draw the mechanism of 1-hexene bromination. See slide show