Xavier University of Louisiana: XULA Digital Commons

Anderson, Jordan

Masthead Logo Pathways
Volume 2015
Issue 1 2014-2015 Article 2
2019
Perseverance
Jordan Anderson
Xavier University of Louisiana, pathways@xula.edu
Follow this and additional works at: https://digitalcommons.xula.edu/pathways_journal
This Essay is brought to you for free and open access by XULA Digital Commons. It has been accepted for inclusion in Pathways by an authorized
editor of XULA Digital Commons. For more information, please contact ksiddell@xula.edu.
Recommended Citation
Anderson, Jordan (2019) "Perseverance," Pathways: Vol. 2015 : Iss. 1 , Article 2.
Available at: https://digitalcommons.xula.edu/pathways_journal/vol2015/iss1/2
 
 
Jordan Anderson  
Perseverance 
I realize that growing up I lived a really easy life. My parents were both successful and 
always provided for me. We never struggled financially, and people credited me solely on the 
success of my parents. I never had to work hard in anything besides homework, and as a result I 
became lazy, nonchalant, and carefree. High school was a wakeup call. Although I could get 
away with being lazy my first few years, by junior and senior year, playing that card no longer 
worked. I began missing opportunities and not being allowed to take part in certain exclusive 
school and extracurricular events. The beginning of senior year was truly a wakeup call, and 
being placed as a regular band member, rather than an officer like every other senior in the band 
ignited a desire within me that still burns today to show that I am ambitious and just as capable 
as anyone else.  
As I turned the brass knob of the backyard door and stepped onto the red carpet of the 
main room of the house, I reached into my blue shorts pocket, checking my cell phone for text 
messages. I dropped the phone onto the cold, wooden floor in shock at the message. I sprinted 
upstairs to my dresser. Yanking open the drawers, I slipped on a blue Nike shirt, tan cargo shorts, 
and blue Adidas tennis shoes, picked up the phone off the floor, and charged out of the house. I 
jogged the five blocks from home to school and thought of what the message had said: “Jordan, 
hurry up and get to school before you miss your audition. You’re next.” I received that message 
at 9:15 in the morning; the time was now 12:01 and there was a second message. It read, “Don’t 
bother coming. Auditions are over.”  
I ran, my arms pumping, and I appreciated that I lived close enough to school that I 
would not have to involve my parents in this mess. I swung around the corner and passed the 
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Anderson: Perseverance
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school’s snowball stand. I prayed for at least one person to still be on campus. Then I noticed one 
of the younger kids in my section. A tenor drummer named Read.  
“Read! Are you finished with your auditions?” I shouted, gasping for breath. 
“I finished them a while ago. Now I’m just waiting for my parents to come pick me up.” 
“Is anyone still upstairs?”    
“Mr. Cee and Mr. Bashel should still be up there.” 
“Oh, good. Well, I’ll check and try to explain why I was late.”  
“Auditions are already over, so I don’t know what good that will do you.”  
“I know, but I should still try something.” 
I walked across the empty parking lot and pushed the bar-handle door open and forced 
myself into the stairwell. My heart slammed to the ground and bounced back up again each step I 
took. As I turned the knob to the band-room door, a flash revealed the presence of my peers, and 
I relaxed. The band’s officers and section leaders, elected the year before, were there and had 
authority over all non-officers. Section leaders only had authority over their sections, chosen by 
Mr. Cee, the band director. Mr. Cee had not mentioned my name in the selection of officers, but 
he also had not chosen a percussion tenor section captain yet. I choked during my previous 
audition, a practice audition before the start of summer to see how much work I needed before 
the actual auditions. Mr. Bashel had lowered his head and said he knew I could do better. This 
time around, if I was not too late, I would do better. 
“I’m sorry, Jordan, but the auditions are over,” Mr. Bashel said. 
Although I had already predicted what he would say, a shock filled my entire body. I had 
written on my calendar and circled the date of the auditions. Twice. I copied the time straight 
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Pathways, Vol. 2015 [2019], Iss. 1, Art. 2
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from the school website. So I refused to leave Mr. Bashel’s presence with those words he left me 
with.  
“Mr. Bashel, were auditions really today? The date on Schoology.com said that they were 
tomorrow.” 
“Oh, well, we had changed the date at the last summer practice. The one that you had 
missed.” Mr. Bashel turned to the officers.  
“Why didn’t anyone tell Jordan about the new audition date?” The officers all looked at 
each other, until one spoke up.   
“I figured Jordan already knew. We should have told him sooner. I tried texting and 
calling him today, but he didn’t answer.”  
Then all eyes went back on me. Mr. Bashel continued.  
“I’m sorry Jordan. We should have contacted you sooner. Don’t worry about the 
auditions. You don’t need to take them.” 
I should have felt relieved, but instead I felt I hadn’t proven my confidence, or that I’d 
improved. For that reason, on the first day of band camp, as Mr. Cee announced the new section 
leaders, based on leadership and audition scores, he did not utter my name. As he pronounced the 
last name, I lowered my eyebrows and glared in resentment. Then Mr. Cee began his speech. It 
was difficult to focus. I sulked. I felt a spark of hope as I caught his last words: “Anyone, officer 
or section leader can be promoted or demoted at any given time.” 
Although I went home with a crushed spirit, I would not let that failure get to me. As I 
stared at new music from the first day of band camp, a fire lit within my spirit. I would show 
them why I should be a section leader. 
3
Anderson: Perseverance
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The sun beat down on band camp for all seven days, each filled with the same routine, 
and band camp seemed more like a military boot camp. Mornings were for conditioning: running 
laps, stretching, and strengthening our muscles with pushups. Some of the younger kids threw up 
and passed out under the the sun, fluids drained from their bodies. Even one of the new section 
leaders tossed his half-digested breakfast onto the baking concrete. Fortunately, I was one of the 
few already conditioned. Then the officers took charge, leading us in marching procedures, and 
practicing basic movements. As the officers led, I wondered if they, once my friends, were now 
arrogant dictators, or if my jealousy gave me that illusion. We went back inside for a water break 
and returned to the brutal conditions for section practice. 
Officer Hammad managed the tenors, and gave Tren, one of the younger students, the 
authority of counting off, and deciding what we play during warm-ups. At this, my blood boiled 
with jealousy.  
“Why would you have Tren lead us instead of me? I’ve been in the section the longest!” 
“Well, Tren got the highest score in auditions, and seems capable.”  
“That’s not fair! You and I both know I couldn't even go to auditions!”  
With that, everyone shouted, “We know.”  
Then officer Hammad continued. “You did audition before the summer, but you didn’t do 
too well.”  
I quit arguing and blew off my steam with a joke. 
Each night as I walked home, I practiced the new material. Each morning, I saw Hammad 
in the band room, earlier than the others, practicing the same material, sometimes playing the 
songs better than I. My goal was to surpass Hammad to become section leader. The tenors were 
4
Pathways, Vol. 2015 [2019], Iss. 1, Art. 2
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one of the few sections in which everyone was equal, rather than having guys who didn't care, or 
practice, or were at a much lower or higher level. We all wanted to contribute to the band. 
As the week went by, the tenors became a strong unit. Mr. Bashel told Mr. Cee how well 
the tenors were doing, and Mr. Cee acknowledged us with a smirk. I stayed at school after camp 
hours to practice in the band room. Hammad noticed my practicing and asked if he could join 
and the tenors hold a private sectional. I agreed and asked Mr. Bashel. 
“Can the tenors have a private sectional?” His face lit up with a pleased expression. 
“Sure.” 
On the last day of camp, I overheard a conversation between Mr. Bashel and Mr. Cee.  
“What do you think of Jordan? I mean, I’ve seen him coming in everyday and he’s really 
been practicing.” 
“Well, Mr. Bashel, I needed to know if I could trust Jordan first. He was supposed to be 
the tenor section leader, but I didn’t know if he would be worthy with an audition like the one he 
had. I didn’t know if he could handle a section if he couldn’t even handle himself. He never used 
to take band seriously.”  
“I know. But he’s a good musician and he has really improved since then. He practices 
more now and seems to really want to be section leader.”  
“You’re right about those things, Mr. Bashel. I think it is time we promote Jordan to 
section leader to see what he is capable of. We don’t want to do to him what we did to Michael 
last year.” 
Mr. Cee walked towards me.  
5
Anderson: Perseverance
Published by XULA Digital Commons, 2019
 
 
“Jordan, I see that you have really stepped up in the past few weeks. I’ve been 
considering promoting you to section leader. I know that you can handle it, and want to continue 
to see you improve. I will announce it to the band sometime next week.  
With the start of school came the announcement. All eyes turned on me as Mr. Cee 
spoke. I gave smirk and looked around at everyone, not saying anything. It was done. I may not 
have been an officer, but section leader was the next best thing.  
The weeks that followed slowed down. I did not practice as aggressively, but I still did 
more than I had before. Mr. Cee decided to try something new with the drum section: placements 
within the section. Auditions determined the placement of each person. I tensed up in the 
audition and got third, with Hammad on top and Dan in second. Out of four tenors, I placed 
third. Mr. Bashel came and explained that the seats weren’t permanent. That if anyone showed 
why they should be in a higher placement, they can be moved. I headed toward the door after a 
long day. The fire was lit again. I would prove that I was not third place material, but first. 
6
Pathways, Vol. 2015 [2019], Iss. 1, Art. 2
https://digitalcommons.xula.edu/pathways_journal/vol2015/iss1/2


English

Perseverance

This module teaches the student to draw Lewis structures, identify bond types present in molecules from IR spectroscopic data and predict features of IR spectrum of molecule

Lawrence, Candace M.

Xavier University of Louisiana
XULA Digital Commons
Course Modules Department of Chemistry
5-31-2019
Organic Chemistry I Drill (CHEM2210D) -
Module 2 - Functional Groups and Infrared
Spectroscopy
Candace M. Lawrence
Xavier University of Louisiana, clawren2@xula.edu
Follow this and additional works at: https://digitalcommons.xula.edu/doc_cm
Part of the Organic Chemistry Commons
This Organic Chemistry I is brought to you for free and open access by the Department of Chemistry at XULA Digital Commons. It has been accepted
for inclusion in Course Modules by an authorized administrator of XULA Digital Commons. For more information, please contact ksiddell@xula.edu.
Recommended Citation
Lawrence, Candace M., "Organic Chemistry I Drill (CHEM2210D) - Module 2 - Functional Groups and Infrared Spectroscopy"
(2019). Course Modules. 8.
https://digitalcommons.xula.edu/doc_cm/8
11 
 
MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY 
 
A STUDENT SHOULD BE ABLE TO: 
 
1. Given a Lewis (dash or dot), condensed, bond-line, or wedge formula of a compound, 
 draw the other representations. 
 
2. Give examples of, and recognize when given the structure, representatives of the 
 following classes of compounds. Also, draw isomers of given compounds. 
 
  Hydrocarbons (compounds containing C and H only) 
   Saturated - alkanes (1°, 2°, 3° H and 1°, 2°, 3°, and 4° C) 
   Unsaturated - alkenes (olefins), alkynes, aromatics 
  Organic compounds containing halogens  
   Alkyl halides = haloalkanes (1°, 2°, 3°) 
  Compounds containing oxygen: 
   C‒O single bonds only: alcohols (1°, 2°, 3°), ethers, phenols 
   C=O compounds: aldehydes, ketones, carboxylic acids, esters, acyl  
    halides, anhydrides 
  Compounds containing nitrogen: amines (1°, 2°, 3°), amides, nitriles, nitros 
  Compounds containing sulfur: thiols, sulfides 
 
3. Identify bond types present in molecules from infrared (IR) spectroscopy data, and 
 predict features of the IR spectrum of molecules from their structures. Important IR 
 absorption frequencies to know include: 
  O‒H (alcohols, hydrogen bonded): 3200-3600 cm-1, strong and broad 
  N‒H: 3200-3600 cm-1, medium intensity 
  O‒H (carboxylic acids): 2500-3500 cm-1, broad peaks of variable intensity 
  C=O: 1650-1800 cm
-1
, strong absorption 
  
 If you need to use other frequencies to identify other functional groups (and sometimes 
you will), a table of IR frequencies will be provided. 
 
4. Know basic IR theory (Hooke’s Law), especially the relationship between energy, 
wavenumbers, and wavelength.  
 
5. Apply concepts learned in Module 1. 
12 
 
 Simplified Table of Main IR Frequencies 
 
Wavenumber, cm
-1
       Bond Peak Description 
 
3200 – 3600 O-H (alcohol) Strong and broad 
 
2500 – 3500 O-H (carboxylic acid) Very broad (over ~ 500 cm-1); often 
  looks like distorted baseline; can  
  obscure C-H bands. 
 
3200 – 3600 N-H (amine, amide) Doublet in case of NH2 group in 
  a primary amine or amide 
 
3300 ≡C-H Usually sharp and strong 
 terminal alkyne  
 
3000 – 3100 =C-H Often weak; shoulder peak adjacent  
 alkene or aromatic to sp
3
 C-H 
   
 
2800 – 3000 C-H (sp3 carbon - hydrogen)  Strong, broad and multi-banded 
 
2100 – 2300 C≡N Medium intensity 
 nitrile 
 
2100 – -2300 C≡C(H) Medium intensity for terminal 
 alkyne alkynes, very weak for internal 
 
1650 – 1800 C=O Very strong; 
                                       (amides, ketones, aldehydes lower frequency for amides and 
                                       carboxylic acids, esters, etc.) when C=O is conjugated 
 
1600 – 1680 C=C Check to see if you have sp2 C-H 
 alkene, aromatic >3000 cm
-1 (if not, it’s completely 
  substituted) 
 
1000-1300 C-O 
 
 
 
13 
 
To best prepare for this module, please work appropriate Skill Builder problems in the textbook. 
Also, all students should attend the IR lab (Organic I lab) to work problems. 
 
A STUDENT WHO HAS MASTERED THE OBJECTIVES FOR THIS UNIT SHOULD BE 
ABLE TO SOLVE THE FOLLOWING PROBLEMS AND RELATED ONES: 
 
1.1 Draw complete Lewis structures (showing all atoms, bonds as lines, and non-bonding 
valence electrons as dots) for the following compounds. Also, name the functional 
groups.  
 
 a) (CH3)2CHCH2CH3   b) CH3(CH2)3CHOHCH3 
 
 
 
 
 
  
 
 
 
 
 e)    f)  (CH3CH2)3CCH2CHO 
 
 
 
 
 
 
 
1.2 Draw a bond-line structure for each of the following compounds. Use dashes and wedges 
to indicate three-dimensional geometry where appropriate. 
 
14 
 
1.2 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
1.3 Draw both condensed and bond-line structures for (a), (b); draw a bond-line formula for 
(c); and name the functional groups present. 
 
             
 
 
 
 
 
 
 
 
1.4 Write condensed formulas for each of the following and name each functional group. 
 
 
 
 
15 
 
1.4  
 
 
 
 
 
 
 
 
 
 
 
2.1 Draw the structure of an example of each of the following classes of compounds. Do not 
 use the symbol “R.” 
 
 a) alkane  b) ether  c) 1° amine  
 
 
 
  
 d) 3° alcohol e) aldehyde  f) 1° alkyl halide 
 
 
 
  
 g) thiol h) alkyne   i) acyl chloride 
 
 
 
 
 
2.2 Name the functional group or groups in each of the following molecules. Indicate 1°, 2°,   
 or 3° where appropriate. 
 
 
16 
 
2.2  
 
 
 
 
 
 
 
 
 
 
2.3  Draw all carbon and hydrogen atoms for each. Indicate the substitution level (1°, 2°, 3°, 
4°) of each carbon and (1°, 2°, 3°) each hydrogen. 
 
   
 
 
 
 
 
 
3.1 Based on the IR data given, what functional group(s) can be present in these compounds? 
 
a) A strong absorption at 1710 cm-1, no N in the molecular formula, no strong 
absorption 3200-3600 cm
-1
 
 
b) A strong absorption at 1720 cm-1 and a broad absorption between  
 2500-3500 cm
-1
. 
 
c) An oxygen-containing compound with a strong absorption at 3350cm-1, no N in 
the molecular formula, no band at 1650-1800cm
-1
. 
 
 
 
3.2 An oxygen-containing compound does not have IR signals in either the 3200-3600 cm
-1
 
region or the 1650-1800 cm
-1
 region. Which of the following functional groups fits this 
IR spectrum? 
 
  a) ROH b) RCOOH c) RCOR d) ROR 
 
 
17 
 
3.3 For each of the following compounds, determine whether or not you would expect the IR 
spectrum to exhibit a signal to the left of 3000 cm
-1
. 
  
  
 
 
3.4 What IR frequencies would enable a chemist to distinguish between these molecules? 
 
 a) CH3CH2OH and CH3CH2OCH2CH3 
 
 b)  
 
 c)  
 
 
3.5 An unknown compound having the formula C6H13N had one peak in its IR spectrum at 
3350cm
-1
 and peaks around 2900 cm
-1
. Which of the following compounds is consistent 
with this? 
  
  
18 
 
3.6 For each of the following IR spectra, identify whether it is consistent with the structure of 
an alkane, an alkene, an alkyne, a ketone, an alcohol, a carboxylic acid, a primary amine, 
a secondary amine, amide, or ester. Explain. 
 
a) 
  
 
 
b) 
  
 
 
c)   
  
 
 
4.1  Explain what wavenumbers are. How does reciprocal centimeters relate to wavelength? 
 
 
 
 
 
19 
 
4.2 Is the absorption for a sp C-H or a sp
3
 C-H higher in energy. Explain.  
 
 
 
 
 
5.1 a) Draw all constitutional isomers of C3H9N and identify the functional group present in   
                each one. Indicate 1°, 2°, or 3°
 
if appropriate. 
 
 
 
 
 
b) Draw at least four constitutional isomers of C4H6O2 with as many functional groups as  
    possible. Identify each functional group. Some molecules may have more than one. 
 
 
 
 
 
5.2 Which of the following compounds is the most soluble in water? Which is the most 
soluble in hexanes? 
  
 
 
5.3 Which compound has the highest boiling point? Which has the lowest? 
  
  
 
 
5.4 Provide hybridizations and approximate bond angles around the atoms that are in bold. 
You may need to add lone pairs to complete the octet.  
                  
           
20 
 
SOLUTIONS TO SAMPLE PROBLEMS: 
1.1 Functional groups: a) alkane; b) 2º alcohol; c) alkene; d) ether; e) ester d) aldehyde.  
 
  
 
  
  
       
 
1.2 Bond-line structures:  
 
21 
 
1.2 continued 
 
 
 
 
1.3 Functional groups: a) alkene; b) aldehyde, 2° alkyl halide; c) alkene, ketone  
 a) CH3CH2CH(CH3)CH=CH2 b) CHOCHCl(CH2)2CH(CH3)2  
 
  
 
 Note: when the carbon vertex points down, the attached groups point down. 
 
 
1.4 a) alkene, 2° alcohol, carboxylic acid; b) alkyne; c) thiol, alkene; d) sulfide 
 
 a) CH2=C(CH3)CH(OH)(CH2)2C(CH3)2CH2CO2H  b) (C2H5)2CHC≡C(CH2)3CH3 
        or CH3CH2CH(C2H5)C≡C(CH2)3CH3 
 
 c) (CH3)2CHCH(SH)CH=CHC(CH3)3 d) (CH3)2CHCH2S(CH2)2CH(C2H5)C(CH3)3 
 
 
2.1 There are numerous other correct answers. These are just one possible answer. 
  
 a) alkane    b) ether    c) 1° amine  
         
        CH3CH2CH3        CH3OCH2CH3          NH2-CH2-CH2CH3 
 
22 
 
2.1 continued 
 d) 3° alcohol  e) aldehyde  f) 1° alkyl halide 
  
  
  
 g) thiol   h) alkyne   i) acyl chloride 
  
  
 
 
2.2 a) alkene   b) aromatic, carboxylic acid  c) aromatic, ketone 
d) amide   e) 2° alcohol, alkyne   f) ester 
g) aromatic ring, anhydride h) thiol    i) sulfide 
 
2.3 a) 
  
 b) 
  
 
3.1 a) aldehyde, ketone, ester, anhydride  b) carboxylic acid c) alcohol 
 
3.2 d 
23 
 
3.3 a) no b) no c) yes d) no e) yes f) yes g) yes h) no 
 
3.4 a) 3200-3400 cm
-1
 (OH) b) 1620-1680 cm
-1
 (C=C) and 3000-3100 cm
-1
 (=C-H)  
 c) 3000-3100 cm
-1
 (=C-H) 
 
3.5 a 
 
3.6 a) primary amine (NH doublet, ~3350 and 3330, sp
3
 C-H 3000-2800cm
-1
)  
 b) alcohol (broad OH, 3310 cm
-1, 
sp
3
 C-H 3000-2800cm
-1
) 
 c) ketone (C=O, 1720 cm
-1
, sp
3
 C-H 3000-2800cm
-1
 ) 
  
 
4.1  Wavenumbers are the same as reciprocal centimeters. This describes how many waves 
there are in one centimeter. As the wavenumber increases, more waves fit in 1 centimeter 
and the wavelength decreases. As wavelength decreases, energy increases. Hence, the 
smaller the wavenumber, the higher the energy.  
 
4.2 sp C-H absorbs at ~3300 cm
-1
, sp
3
 C-H absorbs between 2800-3000cm
-1
. Since 3300cm
-1
 
is higher than 3000cm
-1
, the sp C-H is higher in energy.   
 
 
5.1 a) 
 
  
 b) There are many other C4H6O2 isomers.  
  
 
5.2 a) is most soluble in water; c) is most soluble in hexanes 
 
5.3 b) has the highest BP; c) has the lowest BP 
 
5.4  
 
24 
 
Name _____________________________________________ Second Drill Test (Sample A) 
Organic Chemistry 2210D      Answer All Questions 
 
1. Name the functional group in each of the following compounds, indicating 1°, 2°, or 3° if 
appropriate. 
  
 
 
2. Give specific examples (do not use R) for each of the following types of compounds.  
 
 a) 3° alcohol  b) ester  c) aldehyde  d) sulfide 
 
  
3. Which of these compounds has a band in its IR spectrum nearest 3030 cm
-1
? 
 
 
 
4.  Which of the following functional groups does not show any absorption bands in the 
3200-3500 cm
-1
 region of the infrared spectrum? 
 
  a) alcohols b) primary amines c) secondary amines d) tertiary amines 
 
 
5. What IR frequencies would enable a chemist to distinguish between these? 
 
   (CH3CH2)3N        and       (CH3CH2)2NH 
 
 
 
6. Which of the following compounds has the highest boiling point? 
 
 a) CH3CH2CH2CH3 b) CH3OCH2CH3 c) CH3CH2CH=O d) CH3CH2CH2OH 
  
 
7. Which of the following compounds is the most soluble in water? Which is the most 
 soluble in hexanes? 
 
 a) CH3CH2-S-CH2CH3   b) CH3(CH2)5CH3 
 
 c) CH3-O-CH2CH3    d) CH3(CH2)5CH2Br 
 
 
25 
 
Name _____________________________________________ Second Drill Test (Sample B) 
Organic Chemistry 2210D      Answer All Questions 
 
1.  Draw structures as indicated. 
 
a) Lewis structure of     b) an isomer of  
                  
 
 
 
 
c) condensed formula for    d) a bond-line formula for 
           CH3(CH2)3CH(OH)CH=C(CH3)2 
 
 
 
2. Consider the molecule below. Give: 
  
 
3. Draw the structure of an example (do not use R) of each of the following classes of   
  compounds. 
 a) 1° amine       b) acyl chloride        c) ether  d) 2° alkyl bromide 
 
 
 
 
4. Name the functional group or groups present in each of the following molecules.  
 Indicate 1°, 2°, or 3° when appropriate. 
 
 
5.  Draw at least four constitutional isomers of C5H11NO2 with as many functional groups as 
possible. Identify each functional group. Some molecules may have more than one. 
26 
 
Multiple Choice 
 
1. An oxygen-containing compound which shows no IR absorption at 1650-1800 cm
-1
 or 3200-
3400 cm
-1
 is likely to be what type of compound? 
 
 a) an amide  b) an alcohol  c) a ketone  d) an ether   
 
2. Which of these compounds has a band in its IR spectrum at 1650-1800 cm
-1
? 
    
 
 
3. Which of the following compounds has the highest boiling point? 
 
   a) CH3CH2CH2CH3   b) CH3CH2CH2CH2CH2OH 
  
 c) CH3OCH2CH3   d) CH3CH2CH2OH 
 
4. Which of the following compounds is the least soluble in water? 
 
a) CH3CH2CH2Br   b) (CH3)2CHCH2CH2OH 
 
c) CH3CH2CH2OH   d) (CH3)2CHCH2CH2Br 
 
 
5. Indicate which of the four compounds below is responsible for the IR spectrum shown below. 
Explain your answer. 
  
  


Organic Chemistry I Drill (CHEM2210D) - Module 2 - Functional Groups and Infrared Spectroscopy

Xavier University of Louisiana
XULA Digital Commons
Course Modules Department of Chemistry
5-31-2019
Organic Chemistry Drill (CHEM2210D) -
Module 5- Sample B - Answer Key
Candace M. Lawrence
Xavier University of Louisiana, clawren2@xula.edu
Follow this and additional works at: https://digitalcommons.xula.edu/doc_cm
This Organic Chemistry I is brought to you for free and open access by the Department of Chemistry at XULA Digital Commons. It has been accepted
for inclusion in Course Modules by an authorized administrator of XULA Digital Commons. For more information, please contact ksiddell@xula.edu.
Recommended Citation
Lawrence, Candace M., "Organic Chemistry Drill (CHEM2210D) - Module 5- Sample B - Answer Key" (2019). Course Modules. 19.
https://digitalcommons.xula.edu/doc_cm/19



Organic Chemistry Drill (CHEM2210D) - Module 5- Sample B - Answer Key

This module deals with Alkenes, its structure, properties and synthesi

Organic Chemistry I Drill (CHEM2210D) - Module 8 - Alkenes and eliminations

This module teaches how to identify and explain the processes involved in proton ¹H and carbon-13 nuclear magnetic resonance (NMR) spectroscopy, and mass spectroscopy

Organic Chemistry II Drill (CHEM2220D). Module 1. Sample Problems

This module deals with alpha Carbon Chemistry; enols and enolate

Organic Chemistry II Drill (CHEM2220D). Module 8. Enolates

Xavier University of Louisiana
XULA Digital Commons
Course Modules Department of Chemistry
5-31-2019
Organic Chemistry II Drill (CHEM2220D)
Module 8. Sample Problems
Candace M. Lawrence
Xavier University of Louisiana, clawren2@xula.edu
Follow this and additional works at: https://digitalcommons.xula.edu/doc_cm
Part of the Organic Chemistry Commons
This Organic Chemistry II is brought to you for free and open access by the Department of Chemistry at XULA Digital Commons. It has been accepted
for inclusion in Course Modules by an authorized administrator of XULA Digital Commons. For more information, please contact ksiddell@xula.edu.
Recommended Citation
Lawrence, Candace M., "Organic Chemistry II Drill (CHEM2220D) Module 8. Sample Problems" (2019). Course Modules. 71.
https://digitalcommons.xula.edu/doc_cm/71
2220D – Drill test 9 – Sample problems 
 
1. (5 points) Draw in all of the alpha hydrogens and circle them. 
 
           
 
2. (20 points) Predict the product of each reaction.  Indicate chiral centers with an asterisk (*).   You may use as 
many equivalents as you need to complete the reactions.  COUNT YOUR CARBONS. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
3. (8 points) Propose a synthetic scheme for each transformation.  You must show all Reagents needed and 
EACH synthetic intermediate to receive full credit. COUNT CARBONS. 
 
 
 
 
 
 
 
 
 
 
 
 
4. (8 points) Propose a synthetic scheme for each transformation.  You must show all Reagents needed and 
EACH synthetic intermediate to receive full credit. COUNT CARBONS. 
 
 
 
 
 
 
 
 
 
 
 
 
5. (9 points) Propose a mechanism for the intramolecular Claisen condensation.  You must include all arrows 
and intermediates to receive full credit.  COUNT CARBONS. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
6. Circle the molecule(s) that can form an enol. (3 pts) 
 
 
7. List TWO bases that can deprotonate acetone to a synthetically-valuable extent. List ONE base that 
will NOT deprotonate acetone. (3 pts) 
 
Will deprotonate: 1.    2.   Will NOT deprotonate: 
 
8. Complete these reactions. There may be more than one important product, or it is possible that no 
reaction occurs. Stoichiometry is not given. If you need more than 1 you have it (20 pts) 
(a) 
 
(b)  
 
(c) 
 
(d) 
 
3(e) 
 
3(f) 
 
 
 
 
9. Propose a mechanism for each of these reactions. Be sure to show all intermediates and mechanistic 
arrows. (8 pts) 
a)  
 
 
 
 
 
 
b) 
 
 
 
 
 
 
 
10. Propose syntheses of these compounds. (12 pts) 
a) 
 
 
 
 
 
 
b) 
 
 
 
 
 
 
 
 
 
11. Draw a keto-form for the following enol (4 points):     
                                                             
    
                                                  
 
12.  Draw a mechanism for the following reaction, 6 points: 
 
 
 
 
 
 
13.  Draw the addition and condensation products of the following Aldol reaction (8 points): 
 
 
 
 
 
 
 
14.  Draw the starting material that produces the following Claisen condensation product, 4 points. 
 
 
 
 
 
 
 
 
 
 
 
15.  Give the structure of the major organic product or products expected from the following reactions.  
“No reaction” might be an appropriate answer in some cases.  
Show the stereochemistry of the products if applicable. (5 points each) 
                                                                    
 
 
 
 
16.  Propose a mechanism for the following Aldol condensation reaction (8 points): 
 
 
 
    
 
 
 
 
 
 
  
 
 
 
 
 
 
17. Identify and draw the alpha hydrogens   18. Draw an aldehyde that has     
in this structure (3 pts.)     ‘1’ alpha hydrogen (3 pts).   
  
 
 
 
 
 
19. Complete these reactions. Stoichiometry is not given. If you need more than 1 you have it (24 pts) 
(a) 
 
 
 
 
(b) 
 
(c) 
OH PCC H3O
+
Br2CH2Cl2
 
 
(d) 
 
 
(e) 
 
 
 
 
 
(f) 
  
 
 
 
 
 
 
 
 
 
20. Which base can be used to generate the enolate completely from this compound (3 pts): 
 
21. Propose a mechanism for this reaction. Be sure to show all intermediates and mechanistic arrows. (5 
pts) 
 
 
 
 
 
 
 
 
 
 
 
22. Propose syntheses of these compounds from the given starting materials. (6 pts) 
 
 
 
 
 
 
 
 
23. Identify the reagents used or the products formed in the following reaction sequence- (6 pts) 
 
 
 


Organic Chemistry II Drill (CHEM2220D) Module 8. Sample Problems

This module teaches about alcohols and phenols; ethers and epoxides; thiols and sulfides

Xavier University of Louisiana
XULA Digital Commons
Course Modules Department of Chemistry
5-31-2019
Organic Chemistry II Drill (CHEM2220D).
Module 2. Sample Problems
Candace M. Lawrence
Xavier University of Louisiana, clawren2@xula.edu
Follow this and additional works at: https://digitalcommons.xula.edu/doc_cm
Part of the Organic Chemistry Commons
This Organic Chemistry II is brought to you for free and open access by the Department of Chemistry at XULA Digital Commons. It has been accepted
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Recommended Citation
Lawrence, Candace M., "Organic Chemistry II Drill (CHEM2220D). Module 2. Sample Problems" (2019). Course Modules. 51.
https://digitalcommons.xula.edu/doc_cm/51
2220D – Drill test 2 – Sample Problems 
 
1. (4 points) Provide the IUPAC name for this compound.  Use R and S where appropriate. 
 
 
2.  (4 points) Arrange these compounds by acidic strength, with the most acidic = 1. 
 
 
      __________        __________  __________      __________ 
 
 
3.  (6 points) If the acid/base reaction does not happen, write “No RXN”. If the reaction occurs, draw the 
products of the reaction. 
 
 
 
 
 
4.  Provide the correct reagents and intermediate structure(s) to complete the reaction schemes.  There 
may be more than one correct scheme to complete the synthesis. 
(4 points)      
 
 
 
 
 
 
 
 
 
 
(7 points)   
5. (5 points)  Draw a mechanism for this transformation. Use arrows to show the flow of electrons. 
 
 
 
 
 
6. (20 points) Predict the product(s) of these reactions, including stereochemistry where appropriate.  If 
nothing occurs, write “No RXN”. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
7. What is the IUPAC name of: (4 pts)   
 
 
             
 
8. Which of these bases can deprotonate ethyl alcohol? Circle them. (4 pts) 
 
 
 NaH  NaC≡CCH2CH(CH3)2  CH3CH2NH2  (CH3)2CHCH2SLi 
 
          
9. Propose a mechanism for this transformation. Be sure to include all reactive intermediates and 
mechanistic arrows. (4 pts) 
 
 
 
 
 
 
 
 
 
 
 
10. Complete these reactions. (24 points) 
a.  
 
b.  
 
 
 
c.  
 
d.  
 
e.  
 
f.  
 
 
11. Propose syntheses. (12 points) 
a. 
 
 
 
 
 
 
b. 
 
 
 
 
 
 
12. Draw the structure of a compound having the formula C5H10O that does NOT decolorize (react with) 
Br2/CCl4 and does not produce a blue-green ppt with H2CrO4. The compound also has this 
1
H NMR 
spectrum: 2.2 ppm, m, 1H; 2.1 ppm, s, 3H; 0.9 ppm, d, 6H. (2 pts) 
 
 
 
 
 
 
 
 
 
 
  
13.  Draw the most stable chair conformation of cis-2-isopropoxycyclohexanol (2 points). 
 
 
 
 
14.  Name the following compounds (4 points): 
 
  
                                                  
 
15.  Give the structure of the major organic product or products expected from the following reactions.  
Show the stereochemistry of the products if applicable.  No reaction may be an appropriate answer in 
some cases. (4 points each)  
 
 
 
 
 
 
 
 
 
16.  Propose an efficient synthesis of   each of the following compounds from the given starting material 
and any needed reagents and/or solvents (8 points each): 
 
   
 
 
 
 
 
 
 
 
 
 
 
b)  Tert-butyl methyl ether from tert-butanol and methanol 
                
 
 
 
 
 
 
 
 
17.  Propose a reasonable mechanism for the following reaction (8 points): 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
18. Provide the IUPAC name for this compound. (4 pts) 2. Draw an epoxide. (2 pts) 
 
        
 
 
19. Predict the product(s) of these reactions. (24 points) 
a.   
 
 
 
 
 
b.    
 
 
      
 
 
 
c. 
  
 
 
 
 
d.        
 
 
 
 
 
 
e.  
 
 
 
f. 
  
 
 
20. Provide a synthesis of the desired product using the starting material provided, and any other reagents 
you need. (12 pts) 
a.  
 
 
 
 
 
 
 
 
 
 
 
 
 
b.  
 
 
 
 
 
 
 
 
 
 
 
21. Arrange these compounds by acidity, with most acidic = #1. (4 points) 
   
           
 
22. Propose a mechanism for this transformation. Be sure to include all intermediate structures and 
mechanistic arrows. (4 pts) 
 
 
 
 
 
 
 


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