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OH LDA - в THF, -78 °C (a) There are four possible sites of deprotonation on...
H CH3 1. LDA 2. CHal НН H3C CN H3C CN Monocarbonyl compounds can be alkylated...
H CH3 1. LDA 2. CHal НН H3C CN H3C CN Monocarbonyl compounds can be alkylated at the a position via the use of lithium disopropylamide, a strong, sterically hindered base Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of P-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a pola aprotic solvent such...
1) Draw the major product of the following intramolecular reaction. 2) Draw the major product of...
1) Draw the major product of the following intramolecular
reaction.
2) Draw the major product of the following reaction that begins
with a retro-aldol, followed by an intramolecular aldol
condensation.
3) Determine and draw the structures of compounds
A and B only. Do not draw the
structure of compound X. Place each structure
above its letter. HINT: Both A and
B are esters.
4) Draw a curved arrow mechanism for the following
acid-catalyzed isomerization reaction. You must show all
intermediates....
Give the major organic product of each reaction. 8. a. LDA н b. H c. mild...
Give the major organic product of each reaction. 8. a. LDA н b. H c. mild H NaOH, H,O н a, LDA b. f. н NaOH, H,O, heat c. mild H NaOH, H,O O NaOH, H,O H CYD a. LDA b. d. h. NaOH, H,O, heat c. mild H*, heat 9. Give the major organic product of each intramolecular Aldol reaction. NaOH, H,O a. heat H NaOH, H2O b. heat NaOH, H,O NaOH, H20 d. heat 10. Propose starting materials...
For the following sequence of reactions: 1. LDA (1.2 eq. -78 C) Final Major Organic Product?...
For the following sequence of reactions: 1. LDA (1.2 eq. -78 C) Final Major Organic Product? H 3. HO 4. heat a. Draw the final product (5 points) b. Draw a detailed, arrow pushing mechanism, for all the steps (for full credit, do not skip any steps). (9 pts)
(c) Give the structure of 3, a mechanism for its formation, and an explanation of the...
(c) Give the structure of 3, a mechanism for its formation, and an explanation of the stereochemical outcome of the reaction. You must also state how many peaks you would expect in the 'H NMR spectrum of 3. You do not need to give the multiplicity of the peaks CH2Cl2 [4 MARKS] (d) Draw out a general reaction scheme that presents the different types of evidence that can be gathered to support the occurrence of neighbouring group participation. Critically evaluate...
2 problems REVIEW Topics [References) CH HC OCH Br2 CH3 B H3C CH,OH H₂C CH₂ Electrophilic...
2 problems
REVIEW Topics [References) CH HC OCH Br2 CH3 B H3C CH,OH H₂C CH₂ Electrophilic addition of hypohalous acids to alkenes yields a 1,2-haloalcohol called a halohydrin. Halohydrin formation, however, does not result from the addition of HOBr, for example. Instead the addition is done indirectly by reaction of the alkene with Br, in the presence of water. The reaction also works with Cl2 to give chlorohydrins instead of bromohydrins. The reaction proceeds through a cyclic intermediate known as...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
H CH3 1. LDA 2. CHal НН H3C CN H3C CN Monocarbonyl compounds can be alkylated at the a position via the use of lithium disopropylamide, a strong, sterically hindered base Because only one carbonyl group is available to participate in resonance stabilization of the enolate, the a-hydrogens are less acidic than those of P-dicarbonyl compounds and so a stronger base is necessary to completely convert the compound to the enolate. The reaction occurs in a pola aprotic solvent such...
1) Draw the major product of the following intramolecular
reaction.
2) Draw the major product of the following reaction that begins
with a retro-aldol, followed by an intramolecular aldol
condensation.
3) Determine and draw the structures of compounds
A and B only. Do not draw the
structure of compound X. Place each structure
above its letter. HINT: Both A and
B are esters.
4) Draw a curved arrow mechanism for the following
acid-catalyzed isomerization reaction. You must show all
intermediates....
Give the major organic product of each reaction. 8. a. LDA н b. H c. mild H NaOH, H,O н a, LDA b. f. н NaOH, H,O, heat c. mild H NaOH, H,O O NaOH, H,O H CYD a. LDA b. d. h. NaOH, H,O, heat c. mild H*, heat 9. Give the major organic product of each intramolecular Aldol reaction. NaOH, H,O a. heat H NaOH, H2O b. heat NaOH, H,O NaOH, H20 d. heat 10. Propose starting materials...
For the following sequence of reactions: 1. LDA (1.2 eq. -78 C) Final Major Organic Product? H 3. HO 4. heat a. Draw the final product (5 points) b. Draw a detailed, arrow pushing mechanism, for all the steps (for full credit, do not skip any steps). (9 pts)
(c) Give the structure of 3, a mechanism for its formation, and an explanation of the stereochemical outcome of the reaction. You must also state how many peaks you would expect in the 'H NMR spectrum of 3. You do not need to give the multiplicity of the peaks CH2Cl2 [4 MARKS] (d) Draw out a general reaction scheme that presents the different types of evidence that can be gathered to support the occurrence of neighbouring group participation. Critically evaluate...
2 problems
REVIEW Topics [References) CH HC OCH Br2 CH3 B H3C CH,OH H₂C CH₂ Electrophilic addition of hypohalous acids to alkenes yields a 1,2-haloalcohol called a halohydrin. Halohydrin formation, however, does not result from the addition of HOBr, for example. Instead the addition is done indirectly by reaction of the alkene with Br, in the presence of water. The reaction also works with Cl2 to give chlorohydrins instead of bromohydrins. The reaction proceeds through a cyclic intermediate known as...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
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