Molecular models

 

 

 

Instructions:
(1) (1) THREE OPTIONS:
[i] [preferred] Print the exam, and do it in the normal way;
[ii] Use an iPad;
[iii] If you don’t have a printer or iPad, write out the answers on paper, carefully indicating
which answer goes with which problem.
(2) Sign the Honor Statement in the space below it.
(3) Show your work, and place your name on each page.
(4) The 50-minute limit is working time: start your clock after downloading, printing, etc.
(5) Use of molecular models is encouraged; otherwise this exam is closed-book.
(6) There are four problems.
(7) Exam 2 is an “assignment” on CANVAS; when finished, scan or photograph your completed
exam, and upload it there.
Scoring
Problem Possible Earned
1. 25
2. 30
3. 25
4. 20
Total 100
Honor Statement: I have neither given nor received unauthorized help on this exam.
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(1) (a) Propose a structural reason why 2 is more stable than 1, 3, or 4.
(b) All compounds shown above have the formula C11H14. Use your answer to (a) to
suggest why 2 must be more stable than any other single-bonded compound with this
formula. Show that your argument is rigorously true.
AlBr3
1 2 (93%) 3 (5%) 4 (2%)
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(2) This question concerns the axial/equatorial preferences of two different substituents on two
different six-membered rings.
(a) For each of the four cases 5-8, should the substituent be more stable in the axial position, or
the equatorial positon? Concisely, why?
(b) Reaction of a glycosyl fluoride (9) with a phenol (10) in the presence of a Lewis acid gives
predominantly the axial O-glycoside 11. When the temperature is raised, 11 is converted to
the equatorial C-glycoside 12. Concisely explain the axial/equatorial preferences in 11 and
12.
[c] In the Kochetkov amination, a sugar such as 2’-fucosyllactose (13) reacts with NH3 or NH4+
to give an aminoglycoside (14), entirely in the equatorial form, regardless of protonation
state. Propose an explanation for this equatorial preference. (The answer to this question is
not known: your answer will be graded on logical consistency.)
X X
Z
Z
? 5: X = CH2, Z = C6H5
6: X = CH2, Z = OCH3
7: X = O, Z = C6H5
8: X = O, Z = OCH3
X
Z
O
F
(RO)n +
OH
R
9 10
O
O
(RO)n
R 11
O
(RO)n
HO
R
12
O
+
OH OH
OH
RO
HO
13
“NH3” O
OH
OH
RO
HO NH2
14
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This page left blank intentionally: work space for problem 2.
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(3) Reaction of the tetrahydrocinnolines 15 with dimethyl maleate (16) gives the [3 + 2]
cycloadducts 17 and 18. The major product is 17 rather than 18: concisely explain this
preference.
HN
N
R1
R2
+
CO2Me
CO2Me
15 16
HN N
R1
R2
MeO2C
MeO2C
N
R1
R2
MeO2C
MeO2C
H N
R1
R2
MeO2C
MeO2C
H
17 (major) 18 (minor)
+
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This page deliberately left blank: work space for problem 3.
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(4) A plant used in traditional Chinese medicine yielded a tetracyclic enone whose structure
was first assigned as 19. After investigation, the structure was re-assigned as 20. Suggest
a structural reason why structure 20 might be more plausible than 19.
O
HO
H H H
OH
19
HO
H H
OH
O
H
20
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Sample Solution

 

 

 

 

Rundown of “Blossoms for Algernon”

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blossoms for algernon cover”Flowers for Algernon,” written in 1966 by Daniel Keyes, has properly gotten one of the most notable dream books in world writing. Initially composed as a short story, the tale of Charlie Gordon—the fundamental character of the book—had later been revised as a novel, which helped the writer to completely unveil characters of the primary characters and make the plot total. The epic is written as research center reports, composed by Charlie for his own benefit.

Charlie Gordon is an intellectually incapacitated multi year-old cleaner in a pastry shop. His IQ rate is 68, and along these lines, he had a troublesome youth (and as he later understood, as long as he can remember). His mom, who urgently needed him to be as brilliant as ordinary children, normally beat him at whatever point he didn’t live up to her desires, or when he showed any enthusiasm for his more youthful sister. At last, Charlie’s dad, so as to spare him from consistently expanding ambushes, had to remove the kid from home, and left him being taken care of by Mr. Donner—a bread shop proprietor.

Laborers in the pastry kitchen giggle at Charlie and menace him due to his low knowledge, yet he didn’t get it, and felt that they were chuckling at him since they like him. He goes to the Beekman College Center for Retarded Adults—his fantasy is to get more astute, which, in his comprehension, intended to have the option to peruse and compose. When he found the opportunity, in light of his uncommon will to consider, his educator Alice prescribes Charlie to experience a test mind medical procedure led by specialist Strauss and teacher Nemur: two exceptional researchers who created an approach to make individuals more intelligent through medical procedure.

The activity is fruitful, and in spite of the fact that for the principal couple of days Charlie doesn’t see any distinctions, in certainty he gets more brilliant step by step, at extraordinary rates. He consistently takes an interest in research center tests including Algernon—a shrewd mouse who had experienced a similar medical procedure; though before the activity, Charlie was not ready to try and finish it, as the time goes on, he overcomes Algernon, demonstrating bit by bit expanding results.

Charlie’s knowledge continues developing much after it arrived at the degree of a normal person. He recalls a great deal of difficult subtleties from his youth; understands that what he considered an inviting disposition was really tormenting and mortification; finding this, he understands that individuals are not all that shrewd as he accepted they were. Charlie begins to look all starry eyed at Alice, however understands that he can’t be with her. He peruses a great deal, goes to college, and soon discoveres that he is more intelligent than educators, whom he respected and nearly loved.

Simultaneously, he faces the inclination that educator Nemur and specialist Strauss don’t perceive his mankind and independence; Charlie sees that they treat him as their creation, declining to concede that the past, intellectually impeded Charlie Gordon was additionally a human person. Nemur and Strauss take Charlie to New York to a meeting for which they intend to present him and Algernon as verification

 

s of their logical hypothesis. Charlie, nonetheless, escapes from the gathering, taking Algernon with him, and covers up in a leased loft. There he meets a young lady, Fay; after a few dates, they engage in sexual relations, and start a relationship. Simultaneously, Charlie proceeds with his examinations, and continues recollecting diverse ghastly occasions from quite a while ago. In any case, at last, he understands that Fay is intruding on him from his exploration, so he chooses to come back to the lab.

There he discovers that the aftereffects of the cerebrum medical procedure he had experienced are reversible; besides, the patients debase at awful rates, and end up in a state of mind much more terrible than before the activity. Dreading the relapse, Charlie, be that as it may, acknowledges these realities, and points all his scholarly force (at this point, he is without a doubt the most insightful individual on Earth, with the IQ pace of 185) at examining this impact, which he has called “the impact of Gordon-Algernon,” on the grounds that Algernon has completely endured this impact and kicked the bucket. Charlie covered him close to the lab.

Bit by bit the negative changes become increasingly self-evident. Charlie overlooks names and occasions, and understanding the importance of books he delighted in perusing so as of late has now gotten unthinkable for him. Urgent, he begins a relationship with Alice, yet not for long—the corruption of his character makes living with him convoluted, and despite the fact that for quite a while, he stays at the scholarly degree of a normal individual, Alice is at last driven out.

Charlie winds up as a totally debased individual. From the start, he comes back to Donner’s bread shop, and afterward chooses to go to a psychological refuge. In his last report, in a P.S. he asked the individuals who were going to peruse it to put blossoms on Algernon’s

 

 

 

 

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