READING TEST

65 MINUTES, 52 QUESTIONS

Questions 1–10 are based on the following passage.

The following is an excerpt from the novel The Jungle by Upton Sinclair, written in 1906.

     During the early part of the winter, the family had had money enough to live and a little over to pay their debts with; but when the earnings of Jurgis fell from nine or ten dollars a week (5) to five or six, there was no longer anything to spare. The winter went, and the spring came, and found them still living thus from hand to mouth, hanging on day by day, with literally not a month’s wages between them and starvation. (10) Marija was in despair, for there was still no word about the reopening of the canning factory, and her savings were almost entirely gone. She had had to give up all idea of marrying then; the family could not get along without her—though (15) for that matter she was likely soon to become a burden even upon them, for when her money was all gone, they would have to pay back what they owed her in board. So Jurgis and Ona and Teta Elzbieta would hold anxious conferences (20) until late at night, trying to figure how they could manage this too without starving. 

    Such were the cruel terms upon which their life was possible, that they might never have nor expect a single instant’s respite from worry, (25) a single instant in which they were not haunted by the thought of money. They would no sooner escape, as by a miracle, from one difficulty, than a new one would come into view. In addition to all their physical hardships, there was thus (30) a constant strain upon their minds; they were harried all day and nearly all night by worry and fear. This was in truth not living; it was scarcely even existing, and they felt that it was too little for the price they paid. They were willing to (35) work all the time; and when people did their best, ought they not to be able to keep alive? 

     There seemed never to be an end to the things they had to buy and to the unforeseen contingencies. Once their water pipes froze (40) and burst; and when, in their ignorance, they thawed them out, they had a terrifying flood in their house. It happened while the men were away, and poor Elzbieta rushed out into the street screaming for help, for she did not even (45) know whether the flood could be stopped, or whether they were ruined for life. It was nearly as bad as the latter, they found in the end, for the plumber charged them seventy-five cents an hour, and seventy-five cents for another man (50) who had stood and watched him, and included all the time the two had been going and coming, and also a charge for all sorts of material and extras. And then again, when they went to pay their January’s installment on the house, the (55) agent terrified them by asking them if they had had the insurance attended to yet. In answer to their inquiry he showed them a clause in the deed which provided that they were to keep the house insured for one thousand dollars, (60) as soon as the present policy ran out, which would happen in a few days. Poor Elzbieta, upon whom again fell the blow, demanded how much it would cost them. Seven dollars, the man said; and that night came Jurgis, grim and (65) determined, requesting that the agent would be good enough to inform him, once for all, as to all the expenses they were liable for. The deed was signed now, he said, with sarcasm proper to the new way of life he had learned—the deed (70) was signed, and so the agent had no longer anything to gain by keeping quiet. And Jurgis looked the fellow squarely in the eye, and so the fellow wasted no time in conventional protests, but read him the deed. They would have (75) to renew the insurance every year; they would have to pay the taxes, about ten dollars a year; they would have to pay the water tax, about six dollars a year— (Jurgis silently resolved to shut off the hydrant). This, besides the interest and (80) the monthly installments, would be all—unless by chance the city should happen to decide to put in a sewer or to lay a sidewalk. Yes, said the agent, they would have to have these, whether they wanted them or not, if the city said so.

1. The overall feeling felt by the primary characters throughout the passage can best be summarized as

(A) unbridled optimism.

(B) stoic acceptance.

(C) vengeful rage.

(D) melancholy hopelessness.

2. Marija’s attitude toward her family members is one of

(A) increasing resentment.

(B) mild disapproval.

(C) dutiful obligation.

(D) outright hostility.

3. As used in line 30, “strain” most closely means

(A) sifting.

(B) variety.

(C) burden.

(D) filtration.

4. It can be reasonably inferred that a large obstacle to budgetary planning by Jurgis, Ona, and Teta is

(A) the high likelihood of unforeseen expenses.

(B) their lack of financial discipline.

(C) an unwillingness to openly discuss monetary matters.

(D) the impossibility of finding a place to live.

5. Which option gives the best evidence for the answer to the previous question?

(A) Lines 12–16 (“She had ... upon them”)

(B) Lines 18–21 (“So Jurgis ... starving”)

(C) Lines 32–34 (“This was ... paid”)

(D) Lines 37–39 (“There seemed ... contingencies”)

6. The passage suggests that the family’s overall work ethic is

(A) rather weak.

(B) very strong.

(C) fairly moderate.

(D) easily satisfactory.

7. The feeling that Jurgis has toward authorities in his community is best described as one of

(A) humility.

(B) skepticism.

(C) appreciation.

(D) commitment.

8. Which option gives the best evidence for the answer to the previous question?

(A) Lines 39–42 (“Once ... house”)

(B) Lines 56–61 (“In answer ... few days”)

(C) Lines 67–71 (“The deed ... quiet”)

(D) Lines 82–84 (“Yes ... said so”)

9. As used in line 72 “squarely” most closely means

(A) traditionally.

(B) directly.

(C) corruptly.

(D) humbly.

10. The narrative in lines 61–84 (“Poor Elzbieta ... said so”) primarily serves to illustrate how

(A) much of a challenge Elzbieta and Jurgis had in securing physically safe employment.

(B) easy it was for Elzbieta and Jurgis to verify the terms of their housing contracts.

(C) difficult it was for Elzbieta and Jurgis to determine their precise financial obligations.

(D) likely it was that Elzbieta and Jurgis would resort to violent confrontation to achieve their goals.

Questions 11–21 are based on the following passage and supplementary material.

The following is an article about bedbugs, authored in 2020.

       Many parents, as they lovingly tuck their children into bed, repeat a short rhyme that has been around for centuries: night-night, sleep tight, don’t let the bedbugs bite! This phrase (5) refers to a time when even the wealthy had to deal with the constant scourge of bedbugs and other pests that preyed on sleeping humans. With the advent of modern pesticides, bedbugs were, for a time, largely an issue of the past. (10) However, in the past few years they have come back with a vengeance, once again plaguing people rich and poor and proving very difficult to eradicate.

       One key reason C. lecturlarius (bedbugs) (15) can be so difficult to remove is their physical properties. They are tiny brown bugs that live solely on the blood of other animals, so edible poison traps won’t work the way they do for ants. In addition, they can live months (20) without food which makes starving them out nearly impossible, and they lay eggs which are impervious to regular pest control methods and stick in unreachable nooks and crannies. Most methods that work on adults do not work (25) on eggs and vice versa. To add to the difficulty, the microscopic size of the eggs makes early stage infestations nearly impossible to detect. In the 1950s, however, with the development of dichloro-diphenyl- trichloroethane (DDT), (30) bedbugs met their match. This chemical, when sprayed on a bed, allowed for up to a year of protection from bedbugs. Humanity lived for roughly 40 years without a major infestation. In fact, scientists had a tough time finding live (35) specimens to study. 

       Then, in 1990s, amidst concern for its effect on wildlife, DDT was largely banned; bedbugs slowly began their comeback. By 2010 their numbers were spiking. Because of a huge (40) increase in personal travel since the last time the bugs were an issue, they spread faster than ever. Laundromats, hotels, and libraries became vectors for transmission. Bug eggs can get tucked into suitcases when traveling, or into books that (45) you check out from the library. In communal living areas (like apartment buildings) they can crawl from one apartment to another as they look for human hosts on which to feed. Their bites, inflicted on victims as they sleep, are (50) painful and itchy and continue to appear if the infestation goes unchecked.

       Because DDT is no longer used, the solution to these pests must be multifaceted. Most poisons and bug bombs will not work as the (55) bugs don’t need to eat and the eggs won’t be affected by sprays. The first step in the process is to reduce clutter in the home. These bugs like to live in small nooks and crannies: reducing clutter reduces their living space. Then, vacuum (60) as many porous surfaces as possible to remove any active bugs. This won’t be hugely helpful since regular vacuum cleaners can’t fit into the small spaces where bedbugs choose to reside, but it is a good preliminary step. Finally, the (65) best option for killing both adults and eggs is heat treatment—this needs to be completed by a professional. Eradication specialists will bring portable heaters and temperature sensors into the space to raise the temperature to a level (70) where the bugs can’t survive. The temperature must be maintained for several hours. This treatment, combined with less effective pesticides, can lead to a full eradication.

        Full eradication is quite expensive, however, (75) and due to the recent resurgence of bedbugs as a problem, many people are unaware of the issue until the infestation in their home reaches incredibly high levels. Education seems to be the best way to help people avoid bed bug infes (80) tation as well as its associated costs and stigmas. People should educate themselves as to the best practices to avoid infestations as they travel and bring goods into their homes. Upon suspicion of infection, experts should be called promptly (85) to eradicate the population before it gets out of control and becomes very expensive and time consuming to do so. Only through these methods can individuals have peace of mind that as they sleep that the bedbugs will not bite.

Figure 1

 

11. Based on the passage as a whole, bedbug infestations over the past century can best be described as

(A) consistently eradicated with only a recent uptick in prevalence.

(B) first a major problem, then generally eradicated, and then gradually resurgent.

(C) steadily declining over time, leading to a widespread eradication today.

(D) initially a mild concern, then a significant issue, and yet again a mild concern today.

12. The main function of lines 1–4 (“Many ... bite!”) is to

(A) engage the reader in the passage’s topic by referring to likely common knowledge.

(B) demonstrate the ever-present danger of a household pest.

(C) show how drawing upon childhood memories can lead to scientific discoveries.

(D) explain why bedbugs have drawn more investigative interest than other insects.

13. The primary purpose of lines 14–27 (“One key ... detect”) is to

(A) explain the exterminating techniques most popular among cleaners today.

(B) illustrate the unique challenges in attempting to exterminate bedbugs.

(C) showcase the evolutionary advantages that bedbugs have over other animals.

(D) demonstrate the health dangers that bedbugs pose to humans.

14. It can be reasonably inferred from the passage that DDT is no longer used today because of

(A) excessive costs.

(B) more effective replacement technology.

(C) environmental concerns.

(D) no need for its application.

15. Which option gives the best evidence for the answer to the previous question?

(A) Lines 24–25 (“Most ... versa”)

(B) Lines 36–37 (“Then ... banned”)

(C) Lines 52–53 (“Because ... multifaceted”)

(D) Lines 74–78 (“Full ... levels”)

16. As used in line 51, “unchecked” most closely means

(A) unexamined.

(B) unknown.

(C) uncontrolled.

(D) disappointing.

17. The passage suggests that eradication of bed bugs using heat and moderately effective pesticides is

(A) the only way to effectively control bedbugs.

(B) less expensive than DDT pesticide treatments.

(C) most useful when bedbugs are beginning to emerge in a home.

(D) less preferable to preventative measures.

18. As used in line 82, “practices” most closely means

(A) methods.

(B) performances.

(C) eliminations.

(D) observations.

19. According to Figure 1, the relationship between bedbug complaints and bedbug violations can best be described as

(A) inversely related.

(B) generally proportional.

(C) somewhat equivalent.

(D) mostly not correlated.

20. Based on Figure 1, if the number of bedbug violations continued to increase at the same rate, what would be the most reasonable estimation for the approximate number of bedbug violations in New York City in the year 2012?

(A) 6,500

(B) 9,000

(C) 12,500

(D) 14,000

21. The data from Figure 1 best provide evidence to support which of the following claims from the passage?

(A) Lines 10–13 (“However ... eradicate”)

(B) Lines 32–35 (“Humanity ... study”)

(C) Lines 48–51 (“Their bites ... unchecked”)

(D) Lines 78–80 (“Education ... stigmas”)

Questions 22–31 are based on the following passage.

Peace, Patriotism, and Fireworks, authored in 2020

     The night sky erupted with great displays of sound and light. Every couple of minutes, from dusk till late, the loud, explosive sounds would shake the sky and some unsuspecting and (5) innocent below. It is not lightning or anything nefarious; rather, it is meant to be a symbol of patriotism. It was a week before the Fourth of July, a day meant to celebrate the United States and those who defend it, and the fireworks had (10) already begun. As red, white, and blue colors streaked across the sky, some reveled with pride for their nation, others waited for the explosive reminders of trauma to end, and I sat with my dog as he shivered in fright. (15) Setting off fireworks in celebration of the independence of the United States is considered a tradition today. This tradition started in Boston during the second celebration of the Fourth of July; these displays continued (20) each year thereafter in more cities across the United States. By the mid-nineteenth century, fireworks had become widely available, making it customary for citizens to blast their own into the night sky. While firework displays were (25) historically limited to one night a year, they now go on for days, even weeks, spouting patriotism and enjoyment as their motivation. Beside these seemingly positive motivations, it can be easy to ignore the consequences. (30)

       One consequence is that fireworks may act as a trigger, reminding veterans who suffer from post-traumatic stress disorder (PTSD) of traumatic events from their service. While many veterans are prepared for the explosion-like (35) sounds, firework displays beginning a full week before and continuing a full week after the Fourth of July can be draining. A whopping twenty percent of veterans are thought to suffer from PTSD, and if even a small fraction (40) of them are triggered by fireworks it begs the question: are the joys of fireworks worth the consequences?

      Our nation’s heroes are not the only ones who may experience the detrimental effects (45) of fireworks. Furry companions also can be frightened by the loud blasts above for nights on end. Veterinary practices, animal shelters, andmother animal organizations frequently send out reminders in the weeks leading up to the (50) Fourth of July to protect our pets from running away out of fright. These may include reminders to microchip our pets, keep pets indoors, and take pets on walks early in the day in case they are too afraid to relieve themselves during the (55) fireworks. Their efforts are not without reason. In fact, more pets run away on the night of the Fourth of July than any other night of the year. Add the consecutive days and weeks of firework displays surrounding the Fourth of July, and it is (60) no wonder that animal organizations go to great lengths to keep pet owners informed.

     While the light and sound pollution may trigger veterans and frighten pets, the environmental pollution caused by fireworks can harm (65) us all. Those who set off fireworks are at most risk for experiencing the negative respiratory effects, but add up all the firework displays in the weeks surrounding the Fourth of July, and the consequences for air quality are profound. (70) Many fireworks are also set off above bodies of water. Runoff of pollutants from firework displays into lakes and streams can harm the waterways, affecting wildlife and water quality. 

         The weeks-long displays of fireworks are not (75) sustainable for veterans, pets, or the environment. To truly allow those affected by fireworks peace, it may seem like a harmless option to get rid of fireworks, but this too would have its own consequences. Those who cherish this (80) practice would feel an attack on their patriotic rights, others would be saddened about the end of a tradition, and the remaining would simply continue lighting fireworks. The answer does not seem to be to eradicate fireworks—they do (85) not need to disappear from the night sky—but perhaps their colors, sounds, magic, and consequences could be limited to just that one night in early July.

22. The primary aim of this passage is to

(A) advocate increased respect for patriotic institutions.

(B) convince readers of the merits of a particular viewpoint.

(C) highlight the historical basis for a national holiday.

(D) encourage widespread civil disobedience to combat an injustice.

23. The main function of the letters in parentheses in line 32, “(PTSD),” is to

(A) introduce an abbreviation for a key term that will be used throughout the passage.

(B) remind readers of a definition that had been previously used in the passage.

(C) highlight the initials of an important contributor to sociological research.

(D) use a term with which readers will more likely be familiar to identify an artistic concept.

24. As used in line 37, “draining” most closely means

(A) drying.

(B) escaping.

(C) exhausting.

(D) unloading.

25. The passage suggests that the number of days of summer firework celebrations in the United States has

(A) steadily decreased over time.

(B) remained constant since the first Fourth of July.

(C) greatly increased over the years.

(D) approached zero due to concerns over negative health consequences.

26. Which option gives the best evidence for the answer to the previous question?

(A) Lines 15–19 (“Setting ... July”)

(B) Lines 24–27 (“While firework ... motivation”)

(C) Lines 33–37 (“While many ... draining”)

(D) Lines 58–61 (“Add the ... informed”)

27. It can be reasonably inferred from the passage that the narrator can most personally relate to those who are

(A) pet owners.

(B) military veterans.

(C) patriotic advocates.

(D) those sensitive to airborne pollutants.

28. Which option gives the best evidence for the answer to the previous question?

(A) Lines 12–14 (“others ... fright”)

(B) Lines 30–33 (“One consequence ... service”)

(C) Lines 71–73 (“Runoff ... quality”)

(D) Lines 79–83 (“Those who ... fireworks”)

29. What argumentative techniques does the author utilize in the third paragraph (lines 30–42, “One consequence ...consequences”)?

(A) Historical analogies and appeals to authority

(B) A personal anecdote and political persuasion

(C) Metaphorical language and a humorous aside

(D) Statistical evidence and a rhetorical question

30. As used in line 55, “reason” most closely means

(A) belief.

(B) justification.

(C) mindfulness.

(D) ambition.

31. The author of the passage would most likely find which of the following to be an optimal solution to the problems that she raises?

(A) An increase in historical education programs in schools that teach students about the importance of American independence

(B) Newer fireworks that are able to explode somewhat higher in the air, providing illumination over a wider area

(C) The replacement of fireworks with a laser light show that does not make noise or create smoke

(D) Noise-cancelling headphones for people bothered by large and sudden noises to use during summer evenings

Questions 32–42 are based on the following passages.

Passage 1 is an adaptation of a letter from Daisy Bates, the president of the Arkansas State Conference of the NAACP, to the NAACP executive secretary Roy Wilkins on December 17, 1957. In it she discusses the situation in the Little Rock schools, which had recently been forced by the federal government to integrate.
Passage 2 is an adaptation of the decision in the Supreme Court case Brown v.Board of Education (1954), in which American schools were legally desegregated.

Passage 1

         Conditions are yet pretty rough in the school for the children. Last week, Minnie Jean’s mother ... asked me to gom over to the school with her for a conference with the (5) principal ... Subject of the conference: “Firmer disciplinary measures, and the withdrawal of Minnie Jean from the glee club’s Christmas program.” The principal had informed Minnie Jean in withdrawing her from the program that (10) “When it is definitely decided that [this school will be integrated] and the troops removed, then you will be able to participate in all activities.” We strongly challenged this statement, which he denied making in that fashion. (15) 

         We also pointed out that the treatment of the children had been getting steadily worse for the last two weeks in the form of kicking, spitting, and general abuse. As a result of our visit, stronger measures are being taken against the white (20) students who are guilty of committing these offenses. For instance, a boy who had been suspended for two weeks,... on his return to school, the first day he knocked Gloria Rey into her locker. As a result of our visit, he was given (25) an indefinite suspension.

         The superintendent of schools also requested a conference the same afternoon ... Here, again we pointed out that a three-day suspension given Hugh Williams for a sneak attack perpetrated (30) on one of the ... boys which knocked him out, and required a doctor’s attention, was not sufficient punishment. We also informed him that our investigation revealed that there were many pupils willing to help if given the opportunity, (35) and that President Eisenhower was very much concerned about the Little Rock crisis. He has stated his willingness to come down and address the student body if invited by student leaders of the school. This information was (40) passed on to the principal of the school, but we have not been assured that leadership would be given to children in the school who are willing to organize for law and order. However, we have not abandoned the idea. Last Friday ... I was (45) asked to call Washington and see if we could get FBI men placed in the school ...

Passage 2

     [These students] seek the aid of the courts in obtaining admission to the public schools of their community on a nonsegregated basis. (50) In each instance, they had been denied admission to schools attended by white children under laws requiring or permitting segregation according to race. This segregation was alleged to deprive the plaintiffs of the equal (55) protection of the laws under the Fourteenth Amendment ... [In prior cases it was held that] equality of treatment is accorded when the races are provided substantially equal facilities even though these facilities be separate ...

        The plaintiffs contend that segregated public schools are not “equal” and cannot be made “equal,” and that hence they are deprived of the equal protection of the laws … 

       We come then to the question presented: (65) Does segregation of children in public schools solely on the basis of race, even though the physical facilities and other “tangible” factors may be equal, deprive the children of the minority group of equal educational opportunities? (70) We believe that it does. 

      Segregation of white and [minority] children in public schools has a detrimental effect upon the [minority] children. The impact is greater when it has the sanction of the law, for the (75) policy of separating the races is usually interpreted as denoting the inferiority of the [minority] group. A sense of inferiority affects the motivation of a child to learn. Segregation with the sanction of law, therefore, has a tendency (80) to [slow] the educational and mental development of [minority] children and to deprive them of some of the benefits they would receive in a racially integrated school system ...

      We conclude that in the field of public education (85) the doctrine of “separate but equal” has no place. Separate educational facilities are inherently unequal. Therefore, we hold that the plaintiffs and others similarly situated for whom the actions have been brought are, by reason (90) of the segregation complained of, deprived of the equal protection of the laws guaranteed by the Fourteenth Amendment. This disposition makes unnecessary any discussion whether such segregation also violates the Due Process (95) Clause of the Fourteenth Amendment.

32. Which selection from Passage 1 best indicates that Daisy Bates succeeding in convincing school officials of her point of view?

(A) Lines 13–14 (“We strongly ... fashion”)

(B) Lines 15–18 (“We also ... abuse”)

(C) Lines 18–25 (“As a ... suspension”)

(D) Lines 37–39 (“He has ... school”)

33. It can be most reasonably inferred that the author of Passage 1 has what attitude toward President Eisenhower?

(A) Appreciation for his willingness to intervene in a situation

(B) Disgust with his implementation of policies encouraging segregation

(C) Indifference toward his lack of concern with racial injustice

(D) Respect for his ability to ignore calls for federal interference

34. As used in line 46, “placed” most closely means

(A) settled.

(B) stationed.

(C) planted.

(D) deposited.

35. The students in the Little Rock Schools as described in Passage 1 are

(A) uniformly skeptical of racial diversity.

(B) generally eager to welcome new students.

(C) a mixture of open-mindedness and hostility.

(D) strongly inclined toward deceitful practices.

36. If someone were to argue to the author of Passage 2 that the plaintiffs should pursue other avenues besides the Supreme Court to achieve their goals, the author of Passage 2 would most likely respond that

(A) such an attempt is worthwhile given the likelihood that the Supreme Court will be unable to settle the issue.

(B) they had already attempted to resolve the matter through other authorities and were denied.

(C) segregation in this case is best adjudicated by action of the United States Congress.

(D) they are as likely to find success in their current argument before the Supreme Court as they were in their previous arguments.

37. The author of Passage 2 most likely places the term “equal” in quotation marks in line 61 in order to

(A) show the consistency of the plaintiffs’ ideas with educational practices.

(B) emphasize the inherent inequality in having segregated schools.

(C) quote the personal accounts of eyewitnesses to injustice.

(D) set aside a largely unfamiliar word for a definition.

38. Passage 2 most strongly suggests that minority students at segregated schools are usually

(A) educationally disadvantaged relative to students at integrated schools.

(B) afforded extracurricular opportunities on par with students at all-white schools.

(C) unaware of the lesser quality of their educational experience.

(D) willing to engage in acts of civil disobedience in order to effect lasting change.

39. Which option gives the best evidence for the answer to the previous question?

(A) Lines 50–53 (“In each ... race”)

(B) Lines 56–59 (“In prior ... separate”)

(C) Lines 78–83 (“Segregation ... system”)

(D) Lines 92–95 (“This disposition ... Amendment”)

40. Which choice best summarizes the differences in the argumentative approach between the two passages?

(A) Passage 1 appeals to historical precedent, while Passage 2 appeals to the emotions of readers.

(B) Passage 1 relies on observational evidence, while Passage 2 relies on philosophical consistency. 

(C) Passage 1 utilizes statistics, while Passage 2 utilizes firsthand accounts.

(D) Passage 1 is sensitive to a lack of equality, while Passage 2 is dismissive of such a concern.

41. Which passage has a wider intended audience and why?

(A) Passage 1 since it is written in a more approachable style than Passage 2.

(B) Passage 1 since it is written as a letter from one official to another.

(C) Passage 2 since it announces and justifies a change to public policy.

(D) Passage 2 since it considers the specific personal hardships of the plaintiffs.

42. The author of Passage 1 would most likely argue that the solution to racial inequality outlined in Passage 2 is

(A) inadequate, because even with shared facilities, unequal treatment can still persist.

(B) sufficient, because with a common school building, racial hostility will inevitably diminish.

(C) disappointing, because separate facilities are inherently unequal.

(D) satisfying, since conflict between students immediately decreased once schools achieved full integration.

Questions 43–52 are based on the following passage and supplementary material.

Friedel-Crafts Reactions, written in 2020

      Benzene is an organic compound originally discovered in the early 1800s. It contains six carbon atoms that connect to form an aromatic ring, with each carbon atom also connected (5) to one hydrogen atom. Naturally, it is a by-product of volcanic eruptions and forest fires. Today, it is also a by-product of car exhaust and tobacco smoke. On its own, it is known as a volatile organic compound (VOC) that is (10) carcinogenic to humans. Despite this, chemists have researched ways to modify benzene since its discovery. Scientists hope that by modifying benzene, they can find more uses for the molecule. (15) One such duo is Charles Friedel and James Crafts who, in the late 1800s, published a technique that they believed added a single alkyl sidechain to the benzene molecule. This modification technique is now known as Friedel-Crafts (20) Alkylation. It was originally thought to be revolutionary, but was soon proven to be ineffective due to one unexpected flaw: the polyalkylation of benzene. Unfortunately, Friedel and Crafts did not realize that by adding a (25) single alkyl sidechain, the benzene ring would become more reactive. This meant that the benzene ring would again react after the first reaction, thus adding another sidechain. This process would repeat until the benzene ring (30) was covered in sidechains. Their technique not only added one sidechain—It added six.

      Though Friedel and Crafts discovered a new chemical reaction, this reaction technique was virtually useless to the scientific community (35) because it lacked selectivity. Selectivity causes a reaction to favor one product over another potential product of the reaction. Without selectivity, it is impossible for chemists to isolate the products of their reaction. Not being able to (40) separate one product from another makes a reaction useless because even a small alteration in a molecule can result in adverse effects.

       A famous example showing the importance of the selectivity is the case of a drug known as (45) thalidomide. This drug was marketed toward pregnant women in the mid-1900s with promises to alleviate morning sickness. What the pharmaceutical company that marketed this drug and consumers did not know is that the (50) reaction behind the making of this drug produced two products with remarkably similar structures. One structure was a sedative while the other was teratogenic, meaning it could disrupt the development of a fetus. The drug (55) was banned from production after this fact was realized, but not before countless children around the world had been born with severe birth defects. The negative  consequences from the use of thalidomide hurt the favorability of (60) Friedel-Crafts reactions for a period of time.

      Fortunately, scientists found a way to avoid the negative impact of chemical selectivity by implementing a more controlled reaction process. Scientists modified the benzene reaction (65) to produce a product similar to their original intent, but one that did not add multiple sidechains to the benzene ring. This modified technique came to be known as Friedel-Crafts Acylation, a now widely used technique in the (70) production of benzene-containing products.

          This technique adds a single acyl sidechain to a benzene ring. The addition of the acyl sidechain makes the benzene ring less reactive, preventing multiple sidechains from being (75) added to the benzene ring. Though the sidechain formed through this technique is not the single alkyl sidechain Friedel and Craft had intended, chemists are easily able to achieve an alkyl sidechain product using an additional (80) reduction reaction.

        Since the transition from alkylation to acylation for benzene reactions, chemists’ abilities to safely modify benzene have expanded exponentially. What seemed revolutionary in the (85) late 1800s is now part of undergraduate organic chemistry experiments in courses throughout universities worldwide. Benzene is no longer solely thought of as a carcinogenic and volatile compound. It now used in a variety of products (90) including plastics, drugs, pesticides, detergents, etc. Its importance to modern chemistry, materials science and pharmaceuticals is unquestioned in the scientific community.

Figure 2

43. Which of the following best explains why the author most likely included the discussion of thalidomide in the passage?

(A) To use a specific example to make a general point

(B) To analyze the success of a scientific technique

(C) To illustrate an argument with a personal anecdote

(D) To consider current objections to a newly developed technology

44. Which choice best supports the idea that a failure to break apart the results of a chemical reaction will make the reaction less useful to scientists?

(A) Lines 5–8 (“Naturally ... smoke”)

(B) Lines 15–18 (“One such ... molecule”)

(C) Lines 28–31 (“This process ... added six)”

(D) Lines 39–42 (“Not being ... effects”)

45. As used in line 11, “modify” most closely means

(A) transform.

(B) persuade.

(C) reform.

(D) pronounce.

46. The author most likely uses the word “virtually” in line 34 to convey the idea that

(A) benzene alkylation reactions were more useful in practice than anticipated.

(B) alkylation probably still had some uses despite its general shortcomings.

(C) selectivity is essential to the possibility of a chemical reaction.

(D) scientists embraced the findings of Friedel and Crafts for many applications.

47. It is reasonable to infer from the passage that the negative side effects of thalidomide were most likely

(A) known, yet concealed.

(B) unintentional.

(C) needlessly emphasized.

(D) surprisingly mild.

48. Which option gives the best evidence for the answer to the previous question?

(A) Lines 43–45 (“A famous ... thalidomide”)

(B) Lines 45–47 (“This drug ... sickness”)

(C) Lines 54–58 (“The drug ... defects”)

(D) Lines 58–60 (“The negative ... time”)

49. It can reasonably be inferred from the fifth paragraph, (lines 61–79), that the primary difference between alkylation and acylation is

(A) acylation allows for chemical selectivity, while alkylation does not.

(B) alkylation has wider applicability in scientific processes than acylation.

(C) acylation has more significantly negative health consequences than does alkylation.

(D) alkylation is more affordable to implement than is acylation.

50. Lines 84–87, (“What seemed ... worldwide”), mainly function to suggest that

(A) the negative consequences of Friedel-Crafts reactions are a major curricular focus today.

(B) benzene is no longer utilized as chemical compound.

(C) chemical safety needs to be an increasingly high priority for students to avoid accidents.

(D) acylation has become a widely accepted practice.

51. The information in Figure 2 is most helpful in better understanding the nature of which of the following terms used in the passage?

(A) “selectivity” (line 35)

(B) “morning sickness” (line 47)

(C) “severe birth defects” (line 57–58)

(D) “Friedel-Crafts reactions” (line 60)

52. Based on Figure 2, in what range of days after conception would it be most dangerous for a pregnant mother to consume thalidomide due to the likelihood of it interfering with multiple developmental processes?

(A) Days 21–23

(B) Days 24–26

(C) Days 27–31

(D) Days 32–35