Question 1Methylphenidate (trade name Ritalin) has long been used for the treatment of ADHD,particularly in children where amphetamines (trade name: Adderall/Vyvanse) are notrecommended. Further studies showed that one of the four diastereomers of methylphenidatewas responsible for the activity. That diastereomer (compound 3 below, trade name Focalin) isshown below. A key step in the synthesis is the introduction of the alcohol group in 2 from thealkene in 1.BINBOC1. BH, THF2. H₂O₂/HO-BOC2NOH2multiple stepsHIZOCH 3Focalin (dexmethylphenidate)A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blockingB. Along with introducing the alcohol, this reaction also sets the stereochemistry at the centralgroup to keep the nitrogen from interfering in other reactions. It plays no chemical role here.carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOCgroup does have a physical role here in that it is very large.3

Methylphenidate is substituted with BOC group. It prevents substituted nitrogen to reacted with…

2 3 A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blocking group to keep the nitrogen from interfering in other reactions. It plays no chemical role here. B. Along with introducing the alcohol, this reaction also sets the stereochemistry at the central carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOC group does have a physical role here in that it is very large.

2 3 A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blocking group to keep the nitrogen from interfering in other reactions. It plays no chemical role here. B. Along with introducing the alcohol, this reaction also sets the stereochemistry at the central carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOC group does have a physical role here in that it is very large.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

1. Pick One: Draw one of the two mechanisms shown below. You may draw both for practice. Give the complete, detailed mechanism for the following reaction. Be sure to include an explanation of the region chemistry and stereochemistry. What type of reaction is this? What is the stereochemistry of the product? CH H. H,0 CI
Kinetic control At low temperatures, molecules have low amounts of kinetic energy and therefore predominantly react through the pathway that has the lowest energy of activation and therefore proceeds at a faster rate. The product obtained through this pathway is referred to as the kinetic product. ▼ Part B Give the structure of compound A, the major product when the reaction is conducted at low temperatures. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. ► View Available Hint(s) Love + H-Br -55 °C A NN [1] A ⒸH: 120 EXP. CONT Marvin JS by ChemAxon SOZ O IL H N CI Br 1 P F
Draw the structure(s) of the major organic product(s) of the following reaction after aqueous workup. CH3 CH3 • You do not have to consider stereochemistry. • Include counter-ions, e.g., Na", I, in your submission, but draw them in their own separate sketcher. • If no reaction occurs, draw the organic starting material. Draw one structure per sketcher. Add additional sketchers using the drop- down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu.
Draw the structure(s) of the major organic product(s), including counterions, of the following reaction. HBr H₂O You do not have to consider stereochemistry. • Include counter-ions, e.g., Na*, I, in your submission, but draw them in their own separate sketcher. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. ⚫ Separate multiple products using the + sign from the drop-down menu. n [F F
Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI + H₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. OH • Do not include counter-ions, e.g., Na+, I¯, in your answer. • In cases where there is more than one answer, just draw one.
Draw a structural formula for the more stable carbocation intermediate formed in the reaction shown. CH3CH2 CH₂CH₂CH3 H H + HI • You do not have to consider stereochemistry. • Do not include anionic counter-ions, e.g., I, in your answer. • For cases in which carbocations of the same or similar stability are expected, draw all of the structures. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down me menu. ChemDoodleⓇ [ ] در > Previous Ne:
Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. CH3 I CH₂-O-CHCH3 • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. 85 ▾ ChemDoodle 4 ۴ ] کر
Show how you might synthesize this compound from an alkyl bromide and a nucleophile in an S№2 reaction. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Only draw the reactants. Separate multiple reactants using the + sign from the drop-down menu. • If there is more than one possible combination of alkyl bromide and nucleophile, draw only one combination. • Do not include counter-ions, e.g., Na+, I, in your answer. / CN Submit Answer TAYY ? ChemDoodle Ⓡ Retry Entire Group • #[ ] در 7 more group attempts remaining
In parts 1 and 2 draw the two organic products of this reaction, showing any nonzero formal charges. Then, in part 3 answer the question regarding purification of the reaction mixture. 1. Draw the product with the higher molecular weight here: 2. Draw the product with the lower molecular weight here: