Chapter 10 The Chemistry of Alcohols and Thiols
... balanced half-reaction.) The iodine can be assigned an oxidation number of +7 in periodate and +5 in iodate. How do we know this? Assign +2 to every oxygen because oxygen is divalent and presumably has two bonds to the iodine. (See the top of text p. 456 for a similar case.) Assign a –1 for every ne ...
... balanced half-reaction.) The iodine can be assigned an oxidation number of +7 in periodate and +5 in iodate. How do we know this? Assign +2 to every oxygen because oxygen is divalent and presumably has two bonds to the iodine. (See the top of text p. 456 for a similar case.) Assign a –1 for every ne ...
Heck Reactions
... total synthesis of (-)-triptolide, (-)-triptonide, (+)triptophenolide, and (+)-triptquinonide." J. Org. Chem. 2000, 65, 2208-2217. An application of Crisp’s method for the synthesis of γ-lactones from β-keto esters. ...
... total synthesis of (-)-triptolide, (-)-triptonide, (+)triptophenolide, and (+)-triptquinonide." J. Org. Chem. 2000, 65, 2208-2217. An application of Crisp’s method for the synthesis of γ-lactones from β-keto esters. ...
Methodology for the olefination of aldehydes and ketones via the Meyer-Schuster reaction
... Figure 1. Aldol reaction The homologation of aldehydes and ketones to α,β-unsaturated esters (Fig. 1), an indispensable tool for generating carbon–carbon bonds, is typically achieved using aldol condensation1, Wittig, Horner–Wadsworth–Emmons (HWE), or other olefination methods2,3. Of these, the aldo ...
... Figure 1. Aldol reaction The homologation of aldehydes and ketones to α,β-unsaturated esters (Fig. 1), an indispensable tool for generating carbon–carbon bonds, is typically achieved using aldol condensation1, Wittig, Horner–Wadsworth–Emmons (HWE), or other olefination methods2,3. Of these, the aldo ...
Study guide/lecture topics
... Other nucleophiles for conjugate additions: organocuprates, thiols Conjugate additions of enolates: Michael reaction and Robinson annulation (again) Mechanism clinic: acetylcholinesterase ...
... Other nucleophiles for conjugate additions: organocuprates, thiols Conjugate additions of enolates: Michael reaction and Robinson annulation (again) Mechanism clinic: acetylcholinesterase ...
Lecture 13a - UCLA Chemistry and Biochemistry
... • Why do we not carried out all reactions this way? • Some reactions are just too slow under the conditions (i.e., mortar and pestle does not provide enough heat to overcome the activation energy resulting in a very slow reaction • Some reaction require the strict exclusion of water which is difficu ...
... • Why do we not carried out all reactions this way? • Some reactions are just too slow under the conditions (i.e., mortar and pestle does not provide enough heat to overcome the activation energy resulting in a very slow reaction • Some reaction require the strict exclusion of water which is difficu ...
Exp`t 73
... Dehydration of 2-methylcyclohexanol, 1 (B.P. = 163-166°C) with 85% phosphoric acid yields a mixture of three products: the main product overall (75-80%) is 1-methyl-1-cyclohexene, 2 (B.P. = 110-111 °C); also present are 3-methyl-1-cyclohexene, 3 (B.P.=104 °C) and methylenecyclohexane, 4. The relativ ...
... Dehydration of 2-methylcyclohexanol, 1 (B.P. = 163-166°C) with 85% phosphoric acid yields a mixture of three products: the main product overall (75-80%) is 1-methyl-1-cyclohexene, 2 (B.P. = 110-111 °C); also present are 3-methyl-1-cyclohexene, 3 (B.P.=104 °C) and methylenecyclohexane, 4. The relativ ...
- KCN K+ R KOH + H2O
... (hemiaminal) followed by E1 elimination of H2O. Note that this reaction requires the presence of at least two hydrogens in the starting amine (H+ comes from N; O is protonated before it leaves) ii) Equilibrium favors imine formation when R” = hydroxy, alkoxy, or amino groups; the products called oxi ...
... (hemiaminal) followed by E1 elimination of H2O. Note that this reaction requires the presence of at least two hydrogens in the starting amine (H+ comes from N; O is protonated before it leaves) ii) Equilibrium favors imine formation when R” = hydroxy, alkoxy, or amino groups; the products called oxi ...
MS PowerPoint - Catalysis Eprints database
... Conventional synthesis of MOM-Cl involves HCHO, HCl and CH3OH Produces the by-product bis[chloromethyl]ether (BCME) BCME is a powerful carcinogen and its use is seriously limited Requires considerable tedious handling during isolation H. Kotsuki, Y. Ushio, N. Yoshimura and M. Ochi, J. Org. C ...
... Conventional synthesis of MOM-Cl involves HCHO, HCl and CH3OH Produces the by-product bis[chloromethyl]ether (BCME) BCME is a powerful carcinogen and its use is seriously limited Requires considerable tedious handling during isolation H. Kotsuki, Y. Ushio, N. Yoshimura and M. Ochi, J. Org. C ...
Mechanism of Aldol Condensation
... condensation; the Wieland-Miescher ketone product is an important starting material for many organic syntheses. Aldol condensations are also commonly discussed in university level organic chemistry classes as a good bond-forming reaction that demonstrates important reaction mechanisms.[In its usual ...
... condensation; the Wieland-Miescher ketone product is an important starting material for many organic syntheses. Aldol condensations are also commonly discussed in university level organic chemistry classes as a good bond-forming reaction that demonstrates important reaction mechanisms.[In its usual ...
Organic Reactions Worksheet
... iv) Write the balanced equation for each oxidizing reaction, use [O] convention c. Using any secondary alcohol: i) Give the displayed (structural formula) which it could be oxidized to ii) State which homologous series the products are part of iii) Write the balanced equation for each oxidizing reac ...
... iv) Write the balanced equation for each oxidizing reaction, use [O] convention c. Using any secondary alcohol: i) Give the displayed (structural formula) which it could be oxidized to ii) State which homologous series the products are part of iii) Write the balanced equation for each oxidizing reac ...
Samantha Landolfa Amy Ryan Section 10 Experiment 9 – Alkenes
... catalyst and a dehydrating agent. When the water is eliminated, a carbocation forms, from which a proton is easily abstracted by a weak base such as water or HSO4-. This is the slow, rate-determining step. A double bond forms when the proton on an adjacent carbon is abstracted. The formation of 2met ...
... catalyst and a dehydrating agent. When the water is eliminated, a carbocation forms, from which a proton is easily abstracted by a weak base such as water or HSO4-. This is the slow, rate-determining step. A double bond forms when the proton on an adjacent carbon is abstracted. The formation of 2met ...
Whitten, Davis, and Peck, General Chemistry, 6th Edition
... Recommended CER Experiments to accompany Hornback’s Organic Chemistry, Second Edition The table below matches sections from the book with recommended CER labs. Click on the experiment title to view a PDF of each lab. Go to www.CERLabs.com to search the complete CER database and to learn more about c ...
... Recommended CER Experiments to accompany Hornback’s Organic Chemistry, Second Edition The table below matches sections from the book with recommended CER labs. Click on the experiment title to view a PDF of each lab. Go to www.CERLabs.com to search the complete CER database and to learn more about c ...
... were higher with electron-rich arenes (R1 = Me, OMe) compared to electron-poor ones (R1 = Hal, CF3). The EWG on the alkene is required since only the uncyclized olefins 4 were isolated with electron-neutral alkenes (R4 = alkyl, aryl). The methodology was extended to secondary and primary alcohols (5 ...
Organometallic Chemistry
... • The use of enantiopure allylic boranes in reactions with achiral aldehydes results not only in high diastereoselection, but also in high enantioselection. • Pure (Z)- and (E)- crotyldiisopino campheylboranes can be prepared at low temperature from (Z)- or (E)- crotylpotassium and B-methoxydiisopin ...
... • The use of enantiopure allylic boranes in reactions with achiral aldehydes results not only in high diastereoselection, but also in high enantioselection. • Pure (Z)- and (E)- crotyldiisopino campheylboranes can be prepared at low temperature from (Z)- or (E)- crotylpotassium and B-methoxydiisopin ...
Excercises 6-10
... phenyl-‐1-‐propene! Explain the Markovnikov rule for the regioselectivity of this reaction, using the energy profile of the two possible reaction pathways! Reading Suggestions: Clayden, Greeves, Warren, ...
... phenyl-‐1-‐propene! Explain the Markovnikov rule for the regioselectivity of this reaction, using the energy profile of the two possible reaction pathways! Reading Suggestions: Clayden, Greeves, Warren, ...
Octenes from E1 versus E2 Eliminations
... Add triethylene glycol to a volume level of 1.5 mL in the reaction tube. Add about 0.3 mL of 1bromooctane using your 1-mL pipet with the 2.5-mL plastic syringe and syringe-pipet connector (Common Shelf). Add a 1/2" stir bar and heat the mixture while stirring gently until a small amount of clear liq ...
... Add triethylene glycol to a volume level of 1.5 mL in the reaction tube. Add about 0.3 mL of 1bromooctane using your 1-mL pipet with the 2.5-mL plastic syringe and syringe-pipet connector (Common Shelf). Add a 1/2" stir bar and heat the mixture while stirring gently until a small amount of clear liq ...
NCEA Level 2 Chemistry (91165) 2012
... correct. • In (a) reagent 4 (H2) is correct. • In (a) reagent 3 (PCl3 / PCl5 / SOCl2) is correct. ...
... correct. • In (a) reagent 4 (H2) is correct. • In (a) reagent 3 (PCl3 / PCl5 / SOCl2) is correct. ...
NCEA Level 2 Chemistry (91165) 2012 Assessment Schedule
... correct. • In (a) reagent 4 (H2) is correct. • In (a) reagent 3 (PCl3 / PCl5 / SOCl2) is correct. ...
... correct. • In (a) reagent 4 (H2) is correct. • In (a) reagent 3 (PCl3 / PCl5 / SOCl2) is correct. ...
name Page 1 of 6 Multiple Choice. Choose the best answer for the
... with Pd/C, it reacts with 2 mol equivalents of H2. Hydrogenation with Lindlar's catalysts gives no reaction. Which of the following structures is constant with this information? (a) ...
... with Pd/C, it reacts with 2 mol equivalents of H2. Hydrogenation with Lindlar's catalysts gives no reaction. Which of the following structures is constant with this information? (a) ...
Microwave-Assisted Sulfamide Synthesis
... selective [1,5]. A novel transition-metal-catalyzed process for making unsymmetric sulfamides that was recently reported has several limitations, especially with ortho-isomers [1]. Even though other available methods report high yields, they either require reagents that are not readily accessible or ...
... selective [1,5]. A novel transition-metal-catalyzed process for making unsymmetric sulfamides that was recently reported has several limitations, especially with ortho-isomers [1]. Even though other available methods report high yields, they either require reagents that are not readily accessible or ...
• Pergamon
... MetaHoporphyrins have been used extensively as models for studying cytochrome P-450 monooxygenase activity.! Although these catalysts are known to carry out many useful reactions such as alkene epoxidation and hydrocarbon oxidation, their utility in organic synthesis has been limited. Recently we re ...
... MetaHoporphyrins have been used extensively as models for studying cytochrome P-450 monooxygenase activity.! Although these catalysts are known to carry out many useful reactions such as alkene epoxidation and hydrocarbon oxidation, their utility in organic synthesis has been limited. Recently we re ...
Chapter 1--Title
... The initial keto intermediate undergoes tautomerization to the phenol product Kolbe reaction of sodium phenoxide results in salicyclic acid, a synthetic precursor to acetylsalicylic acid (aspirin) ...
... The initial keto intermediate undergoes tautomerization to the phenol product Kolbe reaction of sodium phenoxide results in salicyclic acid, a synthetic precursor to acetylsalicylic acid (aspirin) ...
Week 11 Problem Set (Solutions)
... relationship between the substituents? We know that elimination reaction has to occur to convert an alcohol to an alkene, and that the most direct route of eliminating alcohols is through an E1 with H3PO4. If the OH and Me were 1,3 to each other, then the elimination could not be controlled. However ...
... relationship between the substituents? We know that elimination reaction has to occur to convert an alcohol to an alkene, and that the most direct route of eliminating alcohols is through an E1 with H3PO4. If the OH and Me were 1,3 to each other, then the elimination could not be controlled. However ...
Final-01 - Yale Department of Chemistry
... we are not only dealing with two cyclohexenes but also the position of the double bond in the ring. A and D are defined. B and C are formed by bromine radical addition to give a tertiary radical that abstracts a hydrogen atom from HBr. In both B and C the reacting conformation must have bromine axia ...
... we are not only dealing with two cyclohexenes but also the position of the double bond in the ring. A and D are defined. B and C are formed by bromine radical addition to give a tertiary radical that abstracts a hydrogen atom from HBr. In both B and C the reacting conformation must have bromine axia ...
Vinylcyclopropane rearrangement
The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring.Intense experimental as well as computational investigations have revealed that mechanistically, the vinylcyclopropane rearrangement can be thought of as either a diradical-mediated two-step and/or orbital-symmetry-controlled pericyclic process. The amount by which each of the two mechanisms is operative is highly dependent on the substrate.Due to its ability to form cyclopentene rings the vinylcyclopropane rearrangement has served several times as a key reaction in complex natural product synthesis.