FREE Trial

When the (R, R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide,

Question:

When the (R, R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofmann product.
(a) Draw the structure of the major (Hofmann) product.
(b) Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with MCPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.
When the (R, R) isomer of the amine shown is
Transcribed Image Text:

(1) excess CHI (2) Ag2O, hea CHCH31 ) CH CH major CHCH MCPBA major

This problem has been solved!


Do you need an answer to a question different from the above? Ask your question!

Step by Step Answer:

Answer rating: 75% (12 reviews)

The key to this problem is to understand that Hofmann elimination oc…View the full answer


answer-question
Answered By
tutor-profile-image
Parvesh Kumar
I am an experienced Mathematics and Statistics tutor with 10 years of experience teaching students and working professionals. I love teaching students who are passionate to learn subjects or wants to understand any mathematics and statistics concept at graduation or master’s level. I have worked with thousands of students in my teaching career. I have helped students deal with difficult topics and subjects like Calculus, Algebra, Discrete Mathematics, Complex analysis, Graph theory, Hypothesis testing, Probability, Statistical Inference and more. After learning from me, students have found Mathematics and Statistics not dull but a fun subject. I can handle almost all curriculum of mathematics. I did B.Sc (mathematics), M.Sc (mathematics), M.Tech (IT) and am also Gate (CS) qualified. I have worked in various college and school and also provided online tutoring to American and Canadian students. I look forward to discussing with you and make learning a meaningful and purposeful
5.00+ 4+ Reviews 10+ Question Solved
Related Book For  answer-question
Organic Chemistry

Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

See More Books
Question Details
Chapter # 19- Amines
Section: Problems
Problem: 22
View Solution
Create a free account to access the answer
Cannot find your solution?
Post a FREE question now and get an answer within minutes. * Average response time.
Question Posted: April 29, 2016 13:19:16
See More Questions

Students also viewed these Organic Chemistry questions

Q:
An unknown X shows a broad absorption band in the infrared at 3200-3550 cm-1 but none in the 1620-1780 cm-1 region. It contains only C, H, and O. A 116-mg sample was treated with an excess of...
A:
The IR indicates the presence of OH and absence of C C......
Q:
An impure sample of zinc (Zn) is treated with an excess of sulfuric acid (H2SO4) to form zinc sulfate (ZnSO4) and molecular hydrogen (H2). (a) Write a balanced equation for the reaction. (b) If...
A:
a Zn s H 2 SO 4 aq ZnSO 4 aq H 2 g b We assume that a pure sample would produce the th......
Q:
(a) When propanol containing deuterium (D, or 2H; rather than hydrogen at the oxyger, CH3CH2CH2OD, is treated with an excess of H2O containing a catalytic amount of NaOH, 1-propanol is formed...
A:
a This exchange occurs essentially through a series of Brnst......
Q:
In evaluating employee performance and determining salary raises, a company uses a large number of subjective and objective criteria gathered from numerous evaluators that are then combined together...
A:
Look at the scatterplot If you do not include last two points with ext......
Q:
On January 1, 2011, the Brunswick Hat Company adopted the dollar-value LIFO retail method. The following data are available for 2011: Required: Calculate the estimated ending inventory and cost of...
A:
Beginning inventory Plus Net purchases Net markups Less Net markdowns Goods available for......
Q:
A 65-kg boy weighs himself by standing on a scale mounted on a skate- board that is rolling down an incline, as shown in Figure. Assume there is no friction so that the force exerted by the incline...
A:
The scale reading the boys apparent weight is the force the scale exerts on the boy Draw......
Q:
Your company does only projects. If the projects performed by your company are for customers external to your company and a profit criterion exists on the project, then your organization is most...
A:
A P......
Q:
Determining Financial Statement Effects of Various Transactions and Identifying Cash Flow Effects According to its annual report, Wendys International serves the best hamburgers in the business and...
A:
Req 1 Req 2 Balance Sheet Income Statement Stmt of Ca......
Q:
A small business in Tokyo, Japan, is experiencing a slump in sales and decided to engage in a sales promotion tactic. Customers who use the store credit card and spend at least 25,000 per invoice are...
A:
Explanation i The process begins with the user entering the sales price ii The user is then prompted......
Q:
Given the following data, calculate a level production plan, quarterly ending inventory, and average quarterly inventory. If inventory carrying costs are $6 per unit per quarter, what is the annual...
A:
Annual cost of carrying safety stock 6 4 100 2 400 Foreca......
Q:
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated. (a) N, N-dimethylhexan-2-amine (b) N, N-diethylhexan-2-amine (c) Cyclohexyldimethylamine (d)...
A:
Orientation of the Cope el......
Q:
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl. (a) Cyclohexanamine (b) N-ethylhexan-2-amine (c) Piperidine (d) Aniline
A:
a Aliphatic diazonium ions ar......
Q:
Ordinary tap water tastes different after it has been boiled. Can you think of the reason why?
A:
The solubility of gases in water decreases......
Q:
What are Bayesian networks? What is special about them?
A:
Bayesian networks also known as belief networks or Bayes nets are a type of probabilistic graphical model used for representing and reasoning about uncertainty and probabilistic relationships among va......
Q:
What type of data can be used in Nave Bayes algorithm? What type of predictions can be obtained from it?
A:
The Nave Bayes algorithm is a probabilistic machine learning algorithm used for classification and probabilistic modeling tasks It is particularly wel......
Q:
What are the commonalities and differences between biological and artificial neural networks?
A:
Biological neural networks such as the human brain and artificial neural networks used in machine learning and artificial intelligence share some commonalities but also have significant differences He......
Q:
What are the advantages and disadvantages of Nave Bayes compared to other machine-learning methods?
A:
Nave Bayes is a simple yet effective machine learning algorithm that is particularly well suited for certain types of classification tasks However like all machine learning methods it has its own set......
Q:
Founded in Melbourne, Australia, in 2009, Flink Labs is an enterprise that develops business solutions by creatively using AI, machine learning, predictive analytics, and design to produce...
A:
Dashboard applications developed by Flink Labs are created for various purposes primarily to provide business solutions These applications utilize AI......
Q:
Briefly describe the differences among transaction processing systems, management information systems, and enterprise resource planning systems.
A:
A transaction processing system is an organized collect......
Q:
On April 29, 2015, Auk Corporation acquires 100% of the outstanding stock of Amazon Corporation (E & P of $750,000) for $1.2 million. Amazon has assets with a fair market value of $1.4 million (basis...
A:
a Amazon Corporation subsidiary is deemed to have sold its assets on April 29 2015 qualified stock p......
Q:
(a) Devise retrosynthetic schemes for all conceivable alkynide anion alkylation syntheses insect pheromones undecane and 2-methylheptadecane. (b) Write reactions for two feasible syntheses of each...
A:
P b Undecane HC C X CH 8CH3 CHC C X CH 7CH3 2 Methylheptadecane after hydrogenat......
Q:
Each of the following names is incorrect. Give the correct name and explain your reasoning. (a) trans-3-Pentene (b) 1, 1-Dimethylethene (c) 2-Methylcyclohexene (d) 4-Methylcyclobutene (e)...
A:
a We designate the position of the double bond by using the lower number of the two numbers......
Q:
Write a structural formula for each of the following: (a) 3-Methylcyclobutene (b) 1-Methylcyclopentene (c) 2, 3-Dimethyl-2-pentene (d) (Z)-3-Hexene (e) (E)-2-Pentene (f) 3, 3, 3-Tribromopropene (g)...
A:
a b......
Becoming - ISBN: 1524763144 - Free Book