Module 7 Problem Set_ Principles of Organic Chemistry with Lab-2021-Gallaher

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12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 1/9 Module 7 Problem Set Due No due date Points 10 Questions 16 Time Limit None Attempt History Attempt Time Score LATEST Attempt 1 26 minutes 10 out of 10 Score for this quiz: 10 out of 10 Submitted Dec 3 at 3:23am This attempt took 26 minutes. 0 / 0 pts Question 1 Your Answer: Define the term heterocycle as it applies to organic molecules. Heterocycles (heterocyclic compounds) are cyclic organic molecules in which one or more carbon atoms are replaced by heteroatoms – elements other than carbon or hydrogen. Answer: Heterocycles (heterocyclic compounds) are cyclic organic molecules in which one or more carbon atoms are replaced by heteroatoms – elements other than carbon or hydrogen. 0 / 0 pts Question 2
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 2/9 Your Answer: What are the two main sub-groups of heterocyclic compounds? aromatic and non-aromatic Answer: Aliphatic and Aromatic 0 / 0 pts Question 3 Your Answer: Explain why pyridine is soluble in water. Pyridine can accept hydrogen bonding interactions due to the lone pair of electrons in nitrogen. And the electronegative N creates a relatively strong dipole moment, making it a polar compound. Answer: There are several factors that explain the ability of pyridine to dissolve in water. First is the ability of pyridine to accept hydrogen bonding interactions from water molecules due to the lone pair of electrons on the nitrogen atom. In addition, the electronegative nitrogen creates a relatively strong dipole moment in the pyridine molecule, thus making pyridine a polar compound overall.
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 3/9 0 / 0 pts Question 4 Your Answer: Is pyridine more likely to act as an acid or a base? Briefly explain . Weak base Answer: Pyridine, like all amines, is a weak base. Amines use the lone pair on the nitrogen atom to accept protons and thus, act as bases. 0 / 0 pts Question 5 Your Answer: Name the two main classes of reactions that the pyridine molecule will undergo. Nucleophilic Aromatic Substitution, electrophilic aromatic substitution Answer: EAS – electrophilic aromatic substitution And NAS – nucleophilic aromatic substitution
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12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 4/9 0 / 0 pts Question 6 Your Answer: Heterocyclic six-membered rings with two or more nitrogen atoms present as part of the ring system are known as what type of heterocycles? Azines Answer: Azines 0 / 0 pts Question 7 Your Answer: Why are the pyrimidines the most biologically important members of the diazine family of molecules? Derivatives of pyrimidines are important bases in the nucleic acids DNA and RNA, namely, cytosine, thymine, and uracil. Answer: Derivatives of pyrimidines are important bases in the nucleic acids DNA and RNA, namely, cytosine, thymine, and uracil. 0 / 0 pts Question 8
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 5/9 Your Answer: Name the most important five-membered heterocyclic compounds containing a single heteroatom substitution and state which element is the heteroatom in each. furan, pyrrole, and thiophene Answer: The most important heterocyclic molecules with five-membered rings are furan (oxygen-based), pyrrole (nitrogen-based), and thiophene (sulfur-based). 0 / 0 pts Question 9 Your Answer: What is the most important difference between five and six-membered heterocycles in terms of the bonding at the heteroatom? the heteroatom of a five-membered ring contributes two electrons (one lone pair) to the aromatic system of the ring to make the molecule aromatic. This is in sharp contrast to six-membered heterocycles where the heteroatom only contributes one electron to the aromatic system.
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 6/9 Answer: The heteroatom of a five-membered ring contributes two electrons (one lone pair) to the aromatic system of the ring to make the molecule aromatic. This is in sharp contrast to six-membered heterocycles where the heteroatom only contributes one electron to the aromatic system. 0 / 0 pts Question 10 Your Answer: Explain why pyrrole is a weaker base than pyridine, even though both are aromatic, heterocyclic amines. the availability of the lone pair. In pyridine, the lone pair is available (not part of the aromatic system) to accept an acidic proton. In pyrrole, this is not the case . Answer: This is due to the availability of the lone pair. In pyridine, the lone pair is available (not part of the aromatic system) to accept an acidic proton. In pyrrole, this is not the case . Protonation of the lone pair of pyrrole destroys the aromatic system and the special stability of aromaticity; thus, pyrrole is much less likely to accept an acidic proton on its nitrogen atom. 0 / 0 pts Question 11
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12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 7/9 Your Answer: Introduction of a nitrogen to the ring of furan, pyrrole, or thiophene creates a family of heterocyclic compounds known as what? azoles . Answer: Azoles 0 / 0 pts Question 12 Your Answer: What is the definition of a fused ring system ? Two (or more) rings are fused together to form a larger molecule. Answer: In a fused-ring system, two (or more) rings are fused together to form a larger molecule. To be fused means that each ring shares two (or more) common atoms as a part of the structure of each ring. 0 / 0 pts Question 13 The molecule indole has what ring fused to the C2-C3 bond of a pyrrole ring?
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 8/9 Your Answer: Fusing a benzene ring to the C2-C3 bond of pyrrole results in a bicyclic, fused-ring compound known as indole Answer: Benzene 0 / 0 pts Question 14 Your Answer: Adenine and guanine, two of the nitrogenous bases present in RNA and DNA, contain what fused ring heterocycle? Purines contain a pyrimidine ring fused to an imidazole ring Answer: Purine 0 / 0 pts Question 15 Identify each of the following heterocycles by name:
12/14/23, 8:43 PM Module 7 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35812?module_item_id=151533 9/9 Your Answer: A. indole B. imidazole C. pyrrole D. pyridine Answer: a. Indole b. Imidazole c. Pyrrole d. Pyridine 10 / 10 pts Question 16 Your Answer: As a reminder, the questions in this review quiz are a requirement of the course and the best way to prepare for the module exam. Did you complete all questions in their entirety? Yes Quiz Score: 10 out of 10
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