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phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes..... Need to build 2- butanone from two-carbon sources... O OH NH

phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes..... Need to build 2- butanone from two-carbon sources... O OH NH

Chemistry
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...
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Could you show the mechanism for Question 4, parts A-C?

phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes.... Need to build 2- butanone from two-carbon sources... MgBr or H H H PH3P=CHCH3 H H OH e MgBr H OH 1. BH3 2. NaOH, H₂O₂ The alkene is symmetrical. Hydroboration, oxymercuration or acid-catalyzed hydration all work for step two. PCC b. Enamines come from ketones or aldehydes. Need to add two carbons to both sides of the ketone... PCC I or in this version, just use a Wittig reagent... O OH MgBr OH POCI 3 pyridine PCC PCC X c. Need to form 3-pentanone, then add two more carbons and institute the double bond.... In this answer, we will dehydrate a symmetrical alcohol... OH MgBr PCC MgBr OH NH3 H* MgBr NH(CH3)2, H* NH I MgBr MgBr Ph3P=CHCH3 NH3 H* OH PCC OH PCC NH çoğça fo PCC
Transcribed Image Text:phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes.... Need to build 2- butanone from two-carbon sources... MgBr or H H H PH3P=CHCH3 H H OH e MgBr H OH 1. BH3 2. NaOH, H₂O₂ The alkene is symmetrical. Hydroboration, oxymercuration or acid-catalyzed hydration all work for step two. PCC b. Enamines come from ketones or aldehydes. Need to add two carbons to both sides of the ketone... PCC I or in this version, just use a Wittig reagent... O OH MgBr OH POCI 3 pyridine PCC PCC X c. Need to form 3-pentanone, then add two more carbons and institute the double bond.... In this answer, we will dehydrate a symmetrical alcohol... OH MgBr PCC MgBr OH NH3 H* MgBr NH(CH3)2, H* NH I MgBr MgBr Ph3P=CHCH3 NH3 H* OH PCC OH PCC NH çoğça fo PCC
3. Construct the following compounds using only the following carbon sources and whatever other inorganic reagents (oxidants, reducing agents, etc): formaldehyde, acetaldehyde, acetone, 1-butanol. a. 4 Carbons becoming 5 Carbons - Need to add one more carbon (must be using formaldehyde)... Thinking backwards - Alcohols form from Grignards reacting with aldehydes... Need to make a Grignard... PBr3 H&H OH НО. OH Br b. 4 Carbons becoming 6 Carbons - Need to add two more carbons (must be using acetaldehyde). Thinking backwards - Chlorides come from alcohols, alcohols come from Grignards with aldehydes... Need a four carbon Grignard... PBr3 Mg PBr3 Br Mg Br MgBr Mg CI c. 4 Carbons becoming 7 Carbons - Need to add three more carbons (must be using acetone). Thinking backwards - Alkenes come from the dehydration of alcohols, alcohols come from Grignards with ketones... Need a four carbon Grignard... BrMg. MgBr H OH OH OH SOCI₂, pyridine {d} POCI3 pyridine more than 4. For the following compounds, construct them from reagents containing no two carbons (with the exception of any Wittig reagent you would like to use with three
Transcribed Image Text:3. Construct the following compounds using only the following carbon sources and whatever other inorganic reagents (oxidants, reducing agents, etc): formaldehyde, acetaldehyde, acetone, 1-butanol. a. 4 Carbons becoming 5 Carbons - Need to add one more carbon (must be using formaldehyde)... Thinking backwards - Alcohols form from Grignards reacting with aldehydes... Need to make a Grignard... PBr3 H&H OH НО. OH Br b. 4 Carbons becoming 6 Carbons - Need to add two more carbons (must be using acetaldehyde). Thinking backwards - Chlorides come from alcohols, alcohols come from Grignards with aldehydes... Need a four carbon Grignard... PBr3 Mg PBr3 Br Mg Br MgBr Mg CI c. 4 Carbons becoming 7 Carbons - Need to add three more carbons (must be using acetone). Thinking backwards - Alkenes come from the dehydration of alcohols, alcohols come from Grignards with ketones... Need a four carbon Grignard... BrMg. MgBr H OH OH OH SOCI₂, pyridine {d} POCI3 pyridine more than 4. For the following compounds, construct them from reagents containing no two carbons (with the exception of any Wittig reagent you would like to use with three
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