Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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QUESTION 1B. Draw the structure using SN1 or SN2. mechanism

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[画像:appropriate Quiz Submission lab in Moodie. LATE Quizzes will NOT be accepted f any reason. 1a. Consider the triol (triple alcohol) drawn below. Directly onto the image below, label each alcohol as 1o, 2o, or 3°. OH OH OH Due to the limitations of the graphics program, the two lone pairs on each O atom are not shown. 1b. The triol is treated with excess HCl. Draw the structures of ALL resulting products (there will obviously be more than one structure). Hint: SN1 or SN2? Your textbook clearly indicates that 1° alcohols react via SN2 and 3° alcohols via SN1. Although not clearly indicted in the textbook, we ASSUME that 2° alcohols use the SN1 mechanism. Use wedge bonds as appropriate for chiral carbons. Note that all three alcohol groups will be chlorinated, not just one or two. That is, there will be three Cl atoms in the same molecule, with no OH groups remaining. 1c. Draw the product that results when the triol is treated with H2CrO4. Note: oxidize all three alcohol groups (or at least try to). 1d. Draw the product that results when the triol is treated with PCC. Note: oxidize all three alcohol groups (or at least try to). Consider the compound below that contains two carboxylic acid and two ketone groups in the same molecule. Due to the limitations of the graphics program, the two lone pairs on each O atom are not shown. HO O O OH 2a. Assume that the compound above can be prepared by the oxidation of a tetra-ol (i.e. four alcohol groups in the same molecule), using H2CrO4 or KMnO4. Draw the structure of this tetra-ol. Use the above structure as a guide so you do not add or remove any carbon atoms from the structure. 2b. Starting the with the tetra-ol from question 2a above, draw the structure of the product that results when the tetra-ol from question 2a (NOT the structure drawn above) is treated with PCC. That is, oxidize all four alcohol groups.]
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Transcribed Image Text:appropriate Quiz Submission lab in Moodie. LATE Quizzes will NOT be accepted f any reason. 1a. Consider the triol (triple alcohol) drawn below. Directly onto the image below, label each alcohol as 1o, 2o, or 3°. OH OH OH Due to the limitations of the graphics program, the two lone pairs on each O atom are not shown. 1b. The triol is treated with excess HCl. Draw the structures of ALL resulting products (there will obviously be more than one structure). Hint: SN1 or SN2? Your textbook clearly indicates that 1° alcohols react via SN2 and 3° alcohols via SN1. Although not clearly indicted in the textbook, we ASSUME that 2° alcohols use the SN1 mechanism. Use wedge bonds as appropriate for chiral carbons. Note that all three alcohol groups will be chlorinated, not just one or two. That is, there will be three Cl atoms in the same molecule, with no OH groups remaining. 1c. Draw the product that results when the triol is treated with H2CrO4. Note: oxidize all three alcohol groups (or at least try to). 1d. Draw the product that results when the triol is treated with PCC. Note: oxidize all three alcohol groups (or at least try to). Consider the compound below that contains two carboxylic acid and two ketone groups in the same molecule. Due to the limitations of the graphics program, the two lone pairs on each O atom are not shown. HO O O OH 2a. Assume that the compound above can be prepared by the oxidation of a tetra-ol (i.e. four alcohol groups in the same molecule), using H2CrO4 or KMnO4. Draw the structure of this tetra-ol. Use the above structure as a guide so you do not add or remove any carbon atoms from the structure. 2b. Starting the with the tetra-ol from question 2a above, draw the structure of the product that results when the tetra-ol from question 2a (NOT the structure drawn above) is treated with PCC. That is, oxidize all four alcohol groups.
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