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Carboxylic Acid Derivatives
Carboxylic Acid Derivatives

... Relative to substitution at an sp3 hybridized carbon, the two-step additionelimination scheme of the carboxylic acid derivatives is more facile…. i.e. it has a lower energy barrier, due to the placement of the negative charge in the intermediate on an atom of higher electronegativity (oxygen). ...
120 Chapter 24: Phenols. Alcohols contain an OH group bonded to
120 Chapter 24: Phenols. Alcohols contain an OH group bonded to

... 24.2: Structure and Bonding (please read) 24.3: Physical Properties (please read). Like other alcohols the OH group of phenols cab participate in hydrogen bonding with other phenol molecules and to water. 24.4: Acidity of Phenols. Phenols are more acidic than aliphatic alcohols pKa ~ 16 H3CH2C O H ...
ppt
ppt

... 24.2: Structure and Bonding (please read) 24.3: Physical Properties (please read). Like other alcohols the OH group of phenols cab participate in hydrogen bonding with other phenol molecules and to water. 24.4: Acidity of Phenols. Phenols are more acidic than aliphatic alcohols pKa ~ 16 H3CH2C O H ...
4.9 Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
4.9 Preparation of Alkyl Halides from Alcohols and Hydrogen Halides

... Figure 4.9 Stabilization of carbocations via the inductive effect ...
Chem 350 Jasperse Ch. 6 Summary of Reaction Types, Ch. 4
Chem 350 Jasperse Ch. 6 Summary of Reaction Types, Ch. 4

... Stability/Reactivity/Selectivity Principles 1. Reactant Stability/Reactivity: The more stable the reactant, the less reactive it will be. In terms of rates, this means that the more stable the reactant, the slower it will react. (The concept here is that the more stable the reactant, the more conten ...
Terrahedron Letters. Vo1.32, No.43, pi 6089
Terrahedron Letters. Vo1.32, No.43, pi 6089

... group over freshly prepared palladium oxide produced the 3-tosyl mannose-4,6-acetonide Several attempts (e.g., bromine in water, etc.) to oxidize 9 to give the corresponding ...
Haloalkanes and Haloarenes
Haloalkanes and Haloarenes

... leading to isocyanides. Similarly nitrite ion also represents an ambident nucleophile with two different points of linkage [–O— N =O]. The linkage through oxygen results in alkyl nitrites while through nitrogen atom, it leads to nitroalkanes. Chemistry 292 ...
THIOALCOHOLS AND DISULFIDES:
THIOALCOHOLS AND DISULFIDES:

... All simple sugars are either polyhydroxy aldehyde or polyhydroxy ketones. Both aldeyde and ketone contain the carbonyl group (C=O). The carbon in C=O must bond to at least one H in an aldehyde. The other single bond must be to carbon or another H but not to O, N,or S. Thus all aldehyde have CH=O gro ...
Alkanes - MsReenChemistry
Alkanes - MsReenChemistry

... Task: Think back to your knowledge of molecular structure, and look at the tables of bond enthalpies in the data booklet to see if you can work out why. ...
Ethers and Epoxides
Ethers and Epoxides

... – Derived by listing the two alkyl groups in the general structure of ROR’ in alphabetical order as separate words and adding the word ether • When both alkyl groups are the same, the prefix diprecedes the name of the alkyl group • (Ethers can be described as symmetrical or unsymmetrical) ...
NUCLEOPHILIC SUBSTITUTION & ELIMINATION ON Csp 3
NUCLEOPHILIC SUBSTITUTION & ELIMINATION ON Csp 3

... Other types of elimination reactions: E2 When a nucleophile Nu: replaces the leaving group on Csp3 in a concerted (smooth, continuous) way this is an SN2 reaction. When the same nucleophile is a strong Broensted base, it can lead to a concerted elimination, or the so-called E2 reaction: ...
Exam 1 Review Sheet Chapter 15 Chemistry 110b
Exam 1 Review Sheet Chapter 15 Chemistry 110b

... mechanisms of acyl vs. alkyl attack, be aware of an example where alkyl attack is favored and why. Lactones-- know the relevant nomenclature, properties, and reactions. [10e, 797-804; 11e, 789-795] ...
Chemistry 262 Quiz 2 Winter 2017 The following
Chemistry 262 Quiz 2 Winter 2017 The following

... a. an SN1-type reaction involving the protonated alcohol as the substrate b. an SN2-type reaction involving the protonated alcohol as the substrate c. an E1-type reaction involving the protonated alcohol as the substrate d. an E2-type reaction involving the protonated alcohol as the substrate e. an ...
4888 Journal of the American Chemical Society 1OO:lS 1 July 19
4888 Journal of the American Chemical Society 1OO:lS 1 July 19

... iodoso compound) which can lead to olefins by a syn elimination process. It is known that amine oxides,2 sulfoxide^,^ and selenoxides4 undergo thermal pericyclic eliminations of hydroxylamine, sulfenic acid (RSOH), and selenenic acid (RSeOH), respectively, to form olefins. Alkyl iodide oxides (iodos ...
Formose reaction controlled by boronic acid - Beilstein
Formose reaction controlled by boronic acid - Beilstein

... contains a number of signals in a wide range of elution time, indicative for the formation of a complicated mixture. On the other hand, the HPLC chart for SPB indicates a broad signal in the region of smaller carbon numbers (Figure 2c), and the chart for pVPB/NaSS exhibits signals in the region of l ...
Carbonyl Condensation Reactions
Carbonyl Condensation Reactions

... conjugated enone as it is formed, especially if reaction conditions are pushed, eg high temperature. Mixed or "crossed" Aldol Reactions — If two different carbonyl compounds are allowed to react in an aldol reaction four products usually result; each carbonyl compound forms an enolate and each enola ...
Functional Groups
Functional Groups

... O-H is a hydroxyl group ...
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... calculations have provided a better understanding of the reaction pathways in some catalytic systems.17 Some catalysts have shown very high reactivities.10a, 12b, 18 However, this reaction typically requires high temperature (>100 oC) and there are only a few reported examples of the reaction at low ...
Bronsted acidic ionic liquid as an efficient and reusable catalyst for
Bronsted acidic ionic liquid as an efficient and reusable catalyst for

... Various reaction parameters such as reaction time, temperature and IL concentration were studied using Bronsted acidic IL [NMP]+HSO4 as an optimized catalyst (Table 2). The results for the transesterification of MAA with 1-butanol demonstrate that chemical equilibrium is reached within 3 h at 80 °C ...
ether - HCC Southeast Commons
ether - HCC Southeast Commons

... are prepared by the sulfuric acid-catalyzed dehydration procedure? What product(s) would you expect if ethanol and 1-propanol were allowed to react together? In what ratio would the products be formed if the two alcohols were of equal reactivity? ...
Arginine- or Lysine-catalyzed Michael Addition of Nitromethane to α
Arginine- or Lysine-catalyzed Michael Addition of Nitromethane to α

... conversion for 24 h. More polar solvents probably maintain near the pKa of a compound and thus nitromethane is more easily deprotonated to be an activated form in alcohols. Although, the conversions are similar in both reactions in ethanol and 2-propanol, ethanol was chosen as a co-solvent for furth ...
Honors Chemistry Name Julien Period _____ Date Chapter 17
Honors Chemistry Name Julien Period _____ Date Chapter 17

... 4. In an aldehyde, the carbon of the carbonyl group is bonded to at least one hydrogen atom. 5. That carbon may also be bonded to another hydrogen, and alkyl group, or an aromatic ring. 6. In a ketone, the carbon of the carbonyl group is bonded to two alkyl groups or aromatic rings. B. Naming aldehy ...
OxorheniumCatalyzed Deoxydehydration of Sugars and Sugar
OxorheniumCatalyzed Deoxydehydration of Sugars and Sugar

... small alcohols ( 3 carbon atoms), such as ethanol, were ineffective (entry 9). For larger ( 5 carbon atoms) alcohols, various alcohols could be used including amyl alcohols, which can be produced by fermentation,[16] but secondary alcohols were found to be generally more favorable than primary alc ...
Methodology for the olefination of aldehydes and ketones via the Meyer-Schuster reaction
Methodology for the olefination of aldehydes and ketones via the Meyer-Schuster reaction

... Alkyne addition to carbonyl groups is relatively insensitive to sterics, whereas the resulting congested tertiary ethoxyalkynyl carbinols are sterically and electronically primed for rearrangement. Having identified this important two-stage synthetic application, we focused our attention on step two ...
4.8 Preparation of Alkyl Halides from Alcohols and Hydrogen
4.8 Preparation of Alkyl Halides from Alcohols and Hydrogen

... electrons in this σ bond can be shared by positively charged carbon because the s orbital can overlap with the empty 2p orbital of positively charged carbon ...
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Tiffeneau–Demjanov rearrangement



The Tiffeneau–Demjanov rearrangement (TDR) is the chemical reaction of a 1-aminomethyl-cycloalkanol with nitrous acid to form an enlarged cycloketone.The Tiffeneau–Demjanov ring expansion, Tiffeneau–Demjanov rearrangement, or TDR, provides an easy way to increase amino-substituted cycloalkanes and cycloalkanols in size by one carbon. Ring sizes from cyclopropane through cyclooctane are able to undergo Tiffeneau–Demjanov ring expansion with some degree of success. Yields decrease as initial ring size increases, and the ideal use of TDR is for synthesis of five, six, and seven membered rings. A principal synthetic application of Tiffeneau–Demjanov ring expansion is to bicyclic or polycyclic systems. Several reviews on this reaction have been published.
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