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1 NAME (Print): SIGNATURE: Chemistry 310N Dr. Brent Iverson 2nd Midterm March 27, 2008 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but there is a reason. I would like to give you a lot of little questions, so you can find ones you can answer and show me what you know, rather than just a few questions that may be testing the one thing you forgot. I recommend you look the exam over and answer the questions you are sure of first, then go back and try to figure out the rest. Also make sure to look at the point totals on the questions as a guide to help budget your time. For synthesis problems G FR PARTIAL CREDIT EVEN IF YU D NT KNW TE ENTIRE ANSWER!!!WRITE DWN WAT YU D KNW IS IN TE REACTIN SEQUENCE SMEWERE. YU WILL GET PARTIAL CREDIT IF IT IS CRRECT Note: You must have your answers written in pen if you want a regrade!!!!
2 Page Points Total (26) (29) (24) (12) (16) (35) (18) (22) (22) (26) (14) (7) (19) (13) (17) (300) % T Score W (W score + Exam Grade) Total Grade
3 onor Code The core values of the University of Texas at Austin are learning, discovery, freedom, leadership, individual opportunity, and responsibility. Each member of the University is expected to uphold these values through integrity, honesty, trust, fairness, and respect toward peers and community. (Your signature)
4 Compound pk a ydrochloric acid -Cl -7 Protonated alcohol RC ydronium ion Carboxylic acids Ammonium ion!-dicarbonyls!-ketoesters!-diesters Water Alcohols Acid chlorides Aldehydes Ketones Esters R RC RC RC 3 RC 2 RC 2 RC 2 C 2 CR' RC 2 C- 3 NR C 2 CR' C 2 CR' CCl C RC 2 CR' CR' Terminal alkynes RC C 25 LDA -N(i-C 3 7 ) 2 40 Terminal alkenes R 2 C C 44 Alkanes C 3 C 2-51
5 Pg 1 (26) 1. (14 points) Suppose a relative of yours is having an MRI. In no more than four sentences, explain to them what is happening when they have the MRI scan. We wil be looking for a minumum of 7 key points here. 2. (4 pts each) In the space provided, write the IUPAC name (including stereochemistry where appropriate) for the following two molecules: 3 C C 3 3 C N C 3 C 3 3. (4 pts) In the space provided, draw the following molecule: (R)-4-Bromo-6-oxoheptanoic acid
6 Pg 2 (29) 4 A). (4 points) In the space provided, write the IUPAC name (including stereochemistry where appropriate) of the following molecule. Cl B) (5 points) Although the molecule above can be drawn and named, it actually could never be prepared and placed in a flask. In no more than two sentences, explain why the molecule shown above could never be isolated. 5. (8 points) Draw the two most important resonance contributing structures of the amide shown below. Be sure to show all lone pairs and formal charges. You do not have to draw arrows on this one. C C N 5. (12 points) n the lines, indicate the hybridization state of each atom indicated by the arrows. N 3 3 N N N C 3 N 2
7 Pg 3 (24) 6. n the lines, write either "YES" or "N" to indicate whether the bonds indicated by the arrows can rotate freely or not. A) (16 pts) N 3 3 N N N C 3 N 2 B) (2 pts) Is the above structure in the protonation state that would exist at p 2.0, 7.0, or 11.0? NTICE TIS 7. (6 pts) List two attributes of amide bonds that lead to stabilization of the folded structures of proteins. Polycyclic Crocodile
8 9. (12 points) For each of the following molecules, draw the indicated number of MST important resonance contributing structures. Be sure to show all lone pairs and formal charges. You do not have to draw any arrows for this question. C C C C C N C C Pg 4 (12)
9 Pg 5 (16) 10. (4 pts) Rank all of the following with respect to relative acidity. The acidic atom in question is indicated in bold and with an underline for each molecule. Place a 1 under the most acidic molecule, and a 4 under the least acidic molecule. F F F 11. (4 pts.) Rank the following in terms of anion stability, with a 1 under the anion that is the most stable and a 4 under the anion that is least stable. F F F 12. (4 pts.) Rank the following in terms of reaction with a strong nucleophile such as -, with a 1 under the molecule that is most reactive, and a 4 under the molecule that is least reactive. Cl N (4 pts.) Rank the following in terms of anion stability, with a 1 under the anion that is the most stable and a 4 under the anion that is least stable. Cl N Please reread the directions to make sure you did not rank backwards!
10 Pg 6 (35) 14. (35 pts.) Complete the mechanism for the following acid catalyzed amide hydrolysis reaction. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I said all the products for each step. IF A NEW CIRAL CENTER IS CREATED IN AN INTERMEDIATE R TE PRDUCTS, MARK IT WIT AN ASTERISK AND LABEL AS "RACEMIC" IF RELEVANT. IN TE BX BY EAC SET F ARRWS, WRITE WIC F TE 4 MECANISTIC ELEMENTS IS INDICATED IN EAC STEP F YUR MECANISM (For example, "Add a proton"). N N Products
11 Pg 7 (18) 14. (cont.) (18 pts.) Complete the mechanism for the following base promoted ester hydrolysis reaction. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I said all the products for each step. IF A NEW CIRAL CENTER IS CREATED IN AN INTERMEDIATE R PRDUCT, MARK IT WIT AN ASTERISKAND LABEL AS "RACEMIC" IF RELEVANT. IN TE BX BY EAC SET F ARRWS, WRITE WIC F TE 4 MECANISTIC ELEMENTS IS INDICATED IN EAC STEP F YUR MECANISM (For example, "Add a proton"). acid-base reaction Chemist opens flask 2) Cl
12 Pg 8 (22) 14. (cont.) (22 pts.) Complete the mechanism for the following reaction involving a Grignard reagent. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I said all the products for each step. IF A NEW CIRAL CENTER IS CREATED IN AN INTERMEDIATE R PRDUCT, MARK IT WIT AN ASTERISKAND LABEL AS "RACEMIC" IF RELEVANT. IN TE BX BY EAC SET F ARRWS, WRITE WIC F TE 4 MECANISTIC ELEMENTS IS INDICATED IN EAC STEP F YUR MECANISM (For example, "Add a proton"). MgBr MgBr Chemist pens Flask 2) Products
13 Pg 9 (22) 16. (22 pts) In the spaces provided, draw all products containing C atoms from the starting material. When in doubt, draw them! When a new chiral center is created put an asterisk next to the chiral ocenter and write "racemic" when racemic mixtures are formed. Also, for aldol reactions D NT DEYDRATE, but draw the intitial product formed. Cl MgCl 1. LiAl SCl 2 3 heat 2 N 2 CuLi 2
14 Pg 10 (26) 16. (24 pts) In the spaces provided, draw all products containing C atoms from the starting material. When in doubt, draw them! When a new chiral center is created put an asterisk next to the chiral center and write "racemic" when racemic mixtures are formed. Also, for aldol reactions D NT DEYDRATE, but draw the intitial product formed. catalytic eat 1. Excess LiAl equivalent Na 2 N heat 1. DIBAL catalytic 2 S 4
15 Pg 11 (14) 17. (14 points) For the following sequences of reactions, draw the predominant organic product or products after ALL the steps. You do not need to draw the intermediates formed along the way. If a new chiral center is created in the reaction that produces a racemic mixture, label the chiral center with an asterisk (*) and write "racemic" underneath. You do not have to draw all of the enantiomers. 1) SCl 2 (6 pts) 2) 2 CuLi 3) 2 4) LiAl 4 5) 2 (8 pts) 1) PBr 3 2) Mg /ether 3) C 2 4) Cl, 2 (Mild acid) 5) SCl 2 6) 2 N 2
16 Pg 12 (7) 17. (7 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! int: this should look familiar as a homework problem. All of the carbons of the product must come from the given starting material.?
17 Pg 13 (19) 17. (cont.) (19 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! All of the carbons of the product must come from the given starting materials.?
18 Pg 14 (13) 17. (cont.) (13 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! All of the carbons of the product must come from the given starting material.? N
19 Pg 15 (17) 18. (9 points) Below are written individual steps of different reaction mechanisms we have learned. Each of these involve a nucleophile reacting with an electrophile. For each step, DRAW A CIRCLE ARUND the nucleophile. No tricks, this is simply here to make sure you can identify nucleophiles versus electrophiles. You do not have to draw any arrows or even draw the products of these steps. + Al Li Cl + 2 N 19. (8 pts) Definitely save this until the end. Acid anhydrides are often used in place of acid chlorides because a less acidic carboxylic acid, not the much stronger acid Cl, is the byproduct of the reaction. In the following reaction of a carbohydrate derivative, acetic anhydride is used to obtain the product in 99% yield as a single stereoisomer. Note that the stereochemistry of the starting cyclic hemiacetal carbon is not indicated. Draw the product of the following transformation in a CAIR FRM and show the single stereoisomer product of this transformation AS A CAIR, which is also the most stable possible CAIR species. 3 C C 3 3 C C 3 Si
Note: You must have your answers written in pen if you want a regrade!!!!
NAME (Print): SIGNATURE: hemistry 310N Dr. Brent Iverson 2nd Midterm March 29, 2007 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
Note: You must have your answers written in pen if you want a regrade!!!!
AME (Print): SIGATURE: hemistry 30 Dr. Brent Iverson nd Midterm March 7, 008 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: hemistry 310N Dr. Brent Iverson 2nd Midterm March 25, 2010 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
Note: You must have your answers written in pen if you want a regrade!!!!
NAME (Print): SIGNATURE: Chemistry 310N Dr. Brent Iverson 1st Midterm Feb. 21, 2008 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
Note: You must have your answers written in pen if you want a regrade!!!!
AME (Print): SIGATURE: hemistry 310 Dr. Brent Iverson 2nd Midterm March 29, 2007 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: Chemistry 310M/318M Dr. ent Iverson 3rd Midterm November 18, 2010 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: Chemistry 320 Dr. Brent Iverson 3rd Midterm April 18, 2013 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: Chemistry 320N Dr. Brent Iverson 1st Midterm Feb. 13, 2014 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: Chemistry 320 Dr. Brent Iverson 2nd Midterm March 23, 2017 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but
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NAME (Print): SIGNATURE: hemistry 310M/318M Dr. Brent Iverson 2nd Midterm November 1, 2007 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit
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NAME (Print): SIGNATURE: hemistry 310M/318M Dr. ent Iverson 2nd Midterm ctober 29, 2009 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
Note: You must have your answers written in pen if you want a regrade!!!!
NAME (Print): SIGNATURE: hemistry 310M/318M Dr. ent Iverson 2nd Midterm November 1, 2007 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
Note: You must have your answers written in pen if you want a regrade!!!!
AME (Print): SIGATURE: Chemistry 310 Dr. Brent Iverson 1st Midterm Feb. 22, 2007 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: Chemistry 320N Dr. Brent Iverson 1st Midterm Feb. 18, 2016 Please print the first three letters of your LAST name in the three boxes Please Note: This test may be a bit long, but
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AME (Print): SIGATURE: Chemistry 310 Dr. Brent Iverson Final May 11, 2006 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there is
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: hemistry 320M/328M Dr. ent Iverson 3rd Midterm November 15, 2012 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
Note: You must have your answers written in pen if you want a regrade!!!!
NAME (Print): SIGNATURE: Chemistry 310N Dr. Brent Iverson 1st Midterm Feb. 23, 2006 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 1st Midterm Feb. 14, 2013 (Sorry about the Valentine's day exam!) Please print the first three letters of your last name in the three boxes Please
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 2nd Midterm March 26, 2015 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 310 Dr. Brent Iverson 2nd Midterm March 22, 2012 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
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AME (Print): SIGATURE: Chemistry 310 Dr. Brent Iverson Final May 18, 2009 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there is
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AME (Print): SIGATURE: hemistry 310 Dr. ent Iverson 3rd Midterm April 26, 2007 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 3rd Midterm April 23, 2015 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 310M/318M Dr. ent Iverson Final exam December 8, 2010 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long,
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): IGATURE: hemistry 320M/328M Dr. Brent Iverson 2nd Midterm ctober 25, 2012 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long,
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: Chemistry 320M/328M Dr. ent Iverson Final December 13, 2018 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
Score: Homework Problem Set 6 Iverson CH320N Due Friday, March 10. NAME (Print): Chemistry 320N Dr. Brent Iverson 6th Homework March 3, 2017
omework Problem Set 6 Iverson 320 Due Friday, March 10 AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 6th omework March 3, 2017 Please print the first three letters of your last name in the three
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: Chemistry 320N Dr. ent Iverson 1st Midterm Feb. 18, 2016 Please print the first three letters of your LAST name in the three boxes Please Note: This test may be a bit long, but
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: Chemistry 320 Dr. Brent Iverson Final May 7, 2014 Please print the first three letters of your last name in the three boxes Please ote: You will do your best if you are relaxed.
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: hemistry 320M/328M Dr. ent Iverson 2nd Midterm ctober 25, 2018 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 3rd Midterm April 17, 2014 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: hemistry 30N Dr. Brent Iverson st Midterm Feb. 9, 05 Please print the first three letters of your LAST name in the three boxes Please Note: This test may be a bit long, but there
Homework Problem Set 11 Iverson CH320N Due Friday, May 5
omework Problem Set 11 Iverson 320 Due Friday, May 5 AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson Problem Set 11 April 28, 2017 Please print the first three letters of your last name in the three
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: hemistry 320N Dr. Brent Iverson 3rd Midterm April 20, 2017 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
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NAME (Print): SIGNATURE: hemistry 310M/318M Dr. Brent Iverson 1st Midterm ctober 4, 2007 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
NAME (Print): Chemistry 610A/618A Dr. Brent Iverson 2nd Exam Oct. 29, 2003 SIGNATURE:
NAME (Print): SIGNATURE: hemistry 610A/618A Dr. ent Iverson 2nd Exam ct. 29, 2003 Please Note: This test may be a bit long, but there is a reason. I would like to give you a lot of little questions, so
Score: Homework Problem Set 9 Iverson CH320N Due Monday, April 17. NAME (Print): Chemistry 320N Dr. Brent Iverson 9th Homework April 10, 2017
omework Problem Set 9 Iverson C0N Due Monday, April 7 NAME (Print): SIGNATURE: Chemistry 0N Dr. ent Iverson 9th omework April 0, 07 Please print the first three letters of your last name in the three boxes
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NAME (Print): SIGNATURE: hemistry 310M/318M Dr. Brent Iverson 1st Midterm ctober 1, 2009 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
Score: NAME (Print): Chemistry 320N Dr. Brent Iverson 3rd Homework February 3, 2017 SIGNATURE:
omework Problem Set 3 Iverson 30N Due Friday February 10 NAME (Print): SIGNATURE: hemistry 30N Dr. ent Iverson 3rd omework February 3, 017 Please print the first three letters of your last name in the
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
AME (Print): SIGATURE: hemistry 310M/318M Dr. Brent Iverson 1st Midterm September 29, 2011 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long,
You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
ME (Print): SIGTURE: hemistry 320 Dr. rent Iverson 2nd Midterm March 26, 2015 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
Homework Problem Set 7 Iverson CH320M/328M Due Friday, Nov. 2
NAME (Print): SIGNATURE: hemistry 320M/328M Dr. Brent Iverson 7th omework October 29, 2018 Please print the first three letters of your last name in the three boxes 1 Score: 2 1. For the following reactions,
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
NAME (Print): SIGNATURE: hemistry 320M/328M Dr. ent Iverson Final December 16, 2017 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
Please note: We routinely xerox a number of exams following initial grading to guard against receiving altered answers during the regrading process.
AME (Print): SIGATURE: hemistry 320M/328M Dr. ent Iverson Final December 13, 2018 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but
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You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.
NAME (Print): SIGNATURE: hemistry 310M/318M Dr. ent Iverson Final December 15, 2009 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but
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AME (Print): SIGATURE: hemistry 310 Dr. ent Iverson Final Exam May 14, 2010 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but there
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NAME (Print): SIGNATURE: hemistry 320M/328M Dr. ent Iverson Final exam December 15, 2012 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,
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AM (Print): SIGATUR: hemistry 320 Dr. ent Iverson Final May 7, 2014 Please print the first three letters of your last name in the three boxes Please ote: You will do your best if you are relaxed. Take
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AME (Print): SIGATURE: hemistry 30M/38M Dr. Brent Iverson st Midterm Sept. 8, 005 Please print the first three letters of your last name in the three boxes Please ote: This test may be a bit long, but
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