Organic+Chemistry+352+Exam+%231+Spring+2020

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Chemistry

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Feb 20, 2024

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Organic Chemistry 352 Exam #1 Name: ______________________ Section: _____________________ And there shall be men standing in that generation, that shall not pass until they shall see an overflowing scourge; for a desolating sickness shall cover the land.   But my disciples shall stand in holy places, and shall not be moved; but among the wicked, men shall lift up their voices and curse God and die.” ( D&C 45:31-32 ) Multiple Choice/Short Answer. Each problem is worth the specified number of points. (80 points total) 1- (5 pts.) Rank the following molecules in order of strongest to weakest acid: a) II. > III. > IV. > I. b) III. > II. > I. > IV. c) IV. > I. > II. > III. d) I. > IV. > III. > II. e) II. > IV. > III. > I. 2- (5 pts.) Rank the following molecules in order of lowest to highest melting point: a) I. < IV. < III. < II. b) I. < III. < IV. < II. c) IV. < I. < II. < III. d) III. < I. < II. < IV. e) II. < IV. < III. < I.
3- (5 pts.) From the following structure, give the IUPAC name of the molecule: ________________________________________________________________________ 4- (5 pts.) From the following IUPAC name, draw the structure of the molecule: ________________________________________________________________________ 5- (5 pts.) From the following structure, give the IUPAC name of the molecule: ________________________________________________________________________ 6- (5 pts.) Draw the resonance structures for the following molecule. ________________________________________________________________________
7- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________ 8- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________ 9- (5 pts.) Which Newman projection shows the orientation of the quaternary ammonium ion intermediate necessary for the elimination that gives the major product of the following reaction? a) b) c) d) e) 10- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________
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11- (5 pts.) Which reaction sequence(s) will result in the desired final product in high yield? (Circle all that apply.) a) 1- HNO 3 /H 2 SO 4 , heat ; 2- CH 3 CH 2 Cl, AlCl 3 ; 3- 2 eq . Br 2 , hv ; 4- 2 eq . CH 3 ONa, CH 3 OH; 5- Zn (Hg), HCl b) 1- HNO 3 /H 2 SO 4 , heat ; 2- Cl 2 , AlCl 3 ; 3- HC≡CNa, DMSO; 4- Zn(Hg), HCl c) 1- Cl 2 , AlCl 3 ; 2- HC≡CNa, DMSO; 3- HNO 3 /H 2 SO 4 , heat ; 4- Zn(Hg), HCl d) 1- CH 3 CH 2 Cl, AlCl 3 ; 2- 2 eq . Br 2 , hv ; 3- 2 eq . CH 3 ONa, CH 3 OH; 4- HNO 3 /H 2 SO 4 , heat ; 5- Zn(Hg), HCl e) 1- Cl 2 , AlCl 3 ; 2- NaNH 2 , NH 3 ; 3- CH 3 CH 2 Cl, AlCl 3 ; 4- 2 eq . Br 2 , hv ; 5- 2 eq . CH 3 ONa, CH 3 OH 12- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________ 13- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________
14- (5 pts.) Draw out the resonance structures for the ortho carbocation intermediate of the following reaction: ________________________________________________________________________ 15- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________ 16- (5 pts.) Predict the product(s) of the following reaction. If there are major and minor products, label them. ________________________________________________________________________
Challenge Problems: Each problem is worth 10 points. These are required problems. (20 pts.) 1- (10 pts.) Show the mechanism in detail for the following reaction. Draw out all of the relevant resonance structures. Be sure to draw all necessary intermediates, arrows, charges, etc. for full credit.
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2- (10 pts.) Devise the BEST target molecule synthesis of the following amine from the given organic reagents. You may use any other necessary reagents (organic or inorganic).
Name: ____________________________ Sister Sorensen-Stowell Chemistry 352 Section 1 Exam #1 May 15, 2020