Module 6 Problem Set_ Principles of Organic Chemistry with Lab-2021-Gallaher

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12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 1/10 Module 6 Problem Set Due No due date Points 10 Questions 14 Time Limit None Attempt History Attempt Time Score LATEST Attempt 1 2,172 minutes 10 out of 10 Score for this quiz: 10 out of 10 Submitted Nov 29 at 8:28pm This attempt took 2,172 minutes. 0 / 0 pts Question 1 Name the following amines using IUPAC systematic nomenclature methodology: a. 2-aminopentane Correct! Correct! b. N-ethyl-N-methylpropy ou Answered ou Answered N- methylpropylamine Correct Answer Correct Answer
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 2/10 c. N-methylcyclohexylam Correct! Correct! d. N-methylpropylamine ou Answered ou Answered N-ethyl-N- methylpropylamine Correct Answer Correct Answer 0 / 0 pts Question 2 Your Answer: Classify each of the following amines as primary, secondary, or tertiary: A. secondary B. secondary C. primary D. tertiary Answer: a. Primary b. Secondary c. Secondary d. Tertiary
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 3/10 0 / 0 pts Question 3 Your Answer: Assuming no significant difference in molecular weight, arrange the following in order of increasing boiling point (lowest BP to highest BP), and provide a brief explanation for your ranking. Amine Alcohol Alkane Alkane > Amine > Alcohol Answer: Alkane < Amine < Alcohol The alkane has no H-bonding attractions. While both the amine and alcohol are capable of forming H-bonds, the O-H is more polar than the N-H, and as a result, the hydrogen bonding in alcohols is stronger than that of amines. 0 / 0 pts Question 4
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12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 4/10 Your Answer: Name the three major synthetic routes to the synthesis of amines as presented in the module. alkylation, reduction or nitrogen compounds, reductive amination Answer: 1. Alkylation of ammonia and other amines (reaction with alkyl halides) 2. Reduction of nitrogen compounds (aromatic nitro, amides, nitriles) 3. Reductive amination 0 / 0 pts Question 5 Your Answer: Briefly explain why amines are stronger bases than amides. The chemistry of all amines is dominated by the lone pair of electrons on the nitrogen atom. The lone pair makes amines both basic and nucleophilic. Answer: Amines and amides can both act as bases by using the lone pair on the nitrogen atom to accept a proton. The lone pair of an amide is less available to accept a proton because it is tied up in resonance with the adjacent carbonyl. Since no resonance is available in amines, the lone pair is more available and hence more basic.
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 5/10 0 / 0 pts Question 6 Your Answer: Provide the IUPAC name and subclassification (1°,2°,3°) for each of the following amides: a) n-mthyl-n-cyclo-pentide, 3° b) n-methylpropamide, 2° c) pentanamide, 1° Answer: a) N,N-diethylcyclohexanecarboxamide; Tertiary b) N-methylpropanamide; Secondary c) Pentanamide; Primary 0 / 0 pts Question 7 Arrange the following list of carboxylic acid derivatives according to their reactivity, from least reactive to most reactive: Acid Anhydride
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 6/10 Your Answer: Ester Acid Halide Amide amide > ester > acid anhydride > acid halide Answer: Amide < Ester < Acid Anhydride < Acid Halide (Least Reactive) --------------------> (Most Reactive) 0 / 0 pts Question 8 What subclassification of amine product would form in each of the following alkylation reactions? You do not have to generate the IUPAC name of any product, just state the degree of structural substitution as 1°, 2°,3°, or quaternary.
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12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 7/10 Your Answer: A. 3° B. 2° C. quaternary D. 1° Answer: a. Tertiary b. Secondary c. Quaternary d. Primary 0 / 0 pts Question 9 Your Answer: Explain why most amides have a planar geometry around the nitrogen atom.
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 8/10 The rotation around the bond is greatly restricted due to the resonance contribution. Answer: Even though the C-N bond is usually represented in structures as a single covalent bond, rotation around this bond is greatly restricted due to the resonance contribution of the lone pair of electrons from the nitrogen to the carbonyl carbon. The resonance hybrid has sufficient C=N character such that it behaves as if it was a true double bond. The geometric consequences of this resonance in amides are that the carbonyl carbon and the nitrogen, as well as the two atoms or groups attached to them, are lying in the same plane (trigonal planar) molecular geometry. 0 / 0 pts Question 10 Your Answer: Explain why the diazonium group is such a good leaving group when it is replaced by a nucleophile in a synthetic reaction. When the diazonium group leaves, it leaves very quickly as a gas and is replaced quickly. Answer: Upon substitution by a nucleophile, the diazonium group leaves as nitrogen gas , which bubbles from the reaction mixture in a very fast and efficient reaction.
12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 9/10 0 / 0 pts Question 11 Your Answer: What does it mean to say that the nitrogen of an amine is in “a reduced state”? meaning all bonds to the nitrogen are to either carbon or hydrogen Answer: This means that all bonds to the nitrogen are either to carbon or hydrogen atoms. 0 / 0 pts Question 12 Your Answer: Explain why reductive amination is the preferred method for the synthesis of amines, as compared to direct alkylation. Reductive amination avoids the potential for polyalkylation and production of mixed products. Answer: In laboratory practice, reductive amination is the preferred method for the synthesis of amines (as compared to direct alkylation), as it avoids the potential for polyalkylation and the production of a mixture of products.
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12/14/23, 8:43 PM Module 6 Problem Set: Principles of Organic Chemistry with Lab-2021-Gallaher https://portagelearning.instructure.com/courses/1430/quizzes/35848?module_item_id=151528 10/10 0 / 0 pts Question 13 Your Answer: Name the following nitriles using IUPAC systematic methodology. pentanenitrile Answer: a. pentanenitrile b. 3-methylbutanenitrile c. cyclopentanecarbonitrile 10 / 10 pts Question 14 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