Aldehydes and Ketones
... When a nucleophile attacks an aldehyde or ketone carbon, there is no leaving group. The incoming nucleophile simply “pushes” the electrons in the pi bond up to the oxygen. (eg: ) Alternatively, if start with the minor resonance contributor: attack by a nucleophile on a carbocation. (eg: ) Afte ...
... When a nucleophile attacks an aldehyde or ketone carbon, there is no leaving group. The incoming nucleophile simply “pushes” the electrons in the pi bond up to the oxygen. (eg: ) Alternatively, if start with the minor resonance contributor: attack by a nucleophile on a carbocation. (eg: ) Afte ...
Chapter 18 – Carbonyl Compounds II (Last Chapter we mostly talk
... to protect a functional group from reacting is quite common in organic chemistry.) (Because they protect functional groups from reacting the groups that are added are called protecting groups. So in the case above, the ketal would be ...
... to protect a functional group from reacting is quite common in organic chemistry.) (Because they protect functional groups from reacting the groups that are added are called protecting groups. So in the case above, the ketal would be ...
Carboxylic Acid Derivatives 1. Background and Properties
... on the alkyl chain relative to the carboxyl carbonyl group. • Nitriles: Simple acyclic nitriles are named by adding nitrile as a suffix to the name of the corresponding alkane (same number of carbon atoms). Chain numbering begins with the nitrile carbon . Commonly, the oic acid or ic acid ending of ...
... on the alkyl chain relative to the carboxyl carbonyl group. • Nitriles: Simple acyclic nitriles are named by adding nitrile as a suffix to the name of the corresponding alkane (same number of carbon atoms). Chain numbering begins with the nitrile carbon . Commonly, the oic acid or ic acid ending of ...
AlCl3 heat HCl
... 24. (6 points) Which alkyl halide in each pair would you expect to be more reactive in an SN2 reaction with a given nucleophile? Explain. ...
... 24. (6 points) Which alkyl halide in each pair would you expect to be more reactive in an SN2 reaction with a given nucleophile? Explain. ...
Preparation of Aldehydes and Ketones
... Water hydrates the carbonyl group. The addition of water to an aldehyde or ketone is catalyzed by either acid or base. The equilibrium reaction forms geminal diols, also called carbonyl hydrates: ...
... Water hydrates the carbonyl group. The addition of water to an aldehyde or ketone is catalyzed by either acid or base. The equilibrium reaction forms geminal diols, also called carbonyl hydrates: ...
Exam 2
... Oxidation states: Be familiar with the various oxidation states of Carbon. Which states are high potential energy (fuels) and which are low potential Energy. Know if a certain reaction is an oxidation or a reduction of the organic compound (e.g a ketone being converted to an alcohol is a reduction) ...
... Oxidation states: Be familiar with the various oxidation states of Carbon. Which states are high potential energy (fuels) and which are low potential Energy. Know if a certain reaction is an oxidation or a reduction of the organic compound (e.g a ketone being converted to an alcohol is a reduction) ...
Problem Set Chapter 13 Solutions February 28, 2013 13.27 Draw
... Now you just have to figure out what the R group is. In order to have the appropriate molecular formula, it has to include 3 carbons and 5 hydrogens. The doublet in the 1H NMR at 6.36 ppm is likely from an alkene (one proton) and the multiplet at 6.09 ppm is likely from the other side of the alkene. ...
... Now you just have to figure out what the R group is. In order to have the appropriate molecular formula, it has to include 3 carbons and 5 hydrogens. The doublet in the 1H NMR at 6.36 ppm is likely from an alkene (one proton) and the multiplet at 6.09 ppm is likely from the other side of the alkene. ...
Organometallic Chemistry
... Reaction of Organoborons Carbonylation Synthesis of Aldehydes and Primary Alcohols • To maximize utilization of valuable alkyl groups, alkenes used for the transfer reaction are hydroborated with 9-BBN. The resultant alkyl-9-BBN derivatives undergo selective migration of the alkyl group when trea ...
... Reaction of Organoborons Carbonylation Synthesis of Aldehydes and Primary Alcohols • To maximize utilization of valuable alkyl groups, alkenes used for the transfer reaction are hydroborated with 9-BBN. The resultant alkyl-9-BBN derivatives undergo selective migration of the alkyl group when trea ...
Synthesis of Benzyl Acetate from Acetic Anhydride
... we can, by Le Chatelier's principle, increase the concentration of either the alcohol or acid, as noted above. If either one is doubled, the theoretical yield increases to 85%. When one is tripled, it goes to 90%. But note that in the example cited the boiling point of the relatively nonpolar ester ...
... we can, by Le Chatelier's principle, increase the concentration of either the alcohol or acid, as noted above. If either one is doubled, the theoretical yield increases to 85%. When one is tripled, it goes to 90%. But note that in the example cited the boiling point of the relatively nonpolar ester ...
Week 11 Problem Set (Solutions)
... (without stereochem) to help you visualize which isomer(s) would be appropriate for specific boxes. Looking at the top section, let’s start by filling in with what we know. Only two structures are provided – the rest of the information is given with reagents. This tests out ability to work backwards ...
... (without stereochem) to help you visualize which isomer(s) would be appropriate for specific boxes. Looking at the top section, let’s start by filling in with what we know. Only two structures are provided – the rest of the information is given with reagents. This tests out ability to work backwards ...
Alcohols - City University of New York
... 1. Nucleophilic substitution on tertiary halides invokes the carbocation but nucleophilic substitution on primary RX avoids the carbocation by requiring the nucleophile to become involved immediately. 2. The E2 reaction requires the strong base to become involved immediately. ...
... 1. Nucleophilic substitution on tertiary halides invokes the carbocation but nucleophilic substitution on primary RX avoids the carbocation by requiring the nucleophile to become involved immediately. 2. The E2 reaction requires the strong base to become involved immediately. ...
Chapter 3. The Concept of Protecting Functional Groups
... molecular Sieves, c) Transacetalization ...
... molecular Sieves, c) Transacetalization ...
AlCl3 in modern chemistry of polyfluoroarenes
... AlCl3 application in the chemistry of polyfluoroarenes beginning since 1995y. As substrates or reagents there are given fluorinated compounds containing two and more fluorine atoms in one aromatic ring and the transformations are systematized according to the type of the reactions taking place. 1. F ...
... AlCl3 application in the chemistry of polyfluoroarenes beginning since 1995y. As substrates or reagents there are given fluorinated compounds containing two and more fluorine atoms in one aromatic ring and the transformations are systematized according to the type of the reactions taking place. 1. F ...
Organic Chemistry I
... 33% p character and are at a lower energy level than the electron pair in the o bond. 33% p character and are at a higher energy level than the electron pair in the o bond. 100% p character and are at a lower energy level than the electron pair in the o bond. 100% p character and are at a higher ene ...
... 33% p character and are at a lower energy level than the electron pair in the o bond. 33% p character and are at a higher energy level than the electron pair in the o bond. 100% p character and are at a lower energy level than the electron pair in the o bond. 100% p character and are at a higher ene ...
Carbenes and Nitrenes: Structure, generaNon and reacNvity
... Then, N-‐heterocyclic carbenes (NHCs) already seen. The first applica4ons of thiazolydenes in umpolung organocatalysis were reported as early as 1943 (J. Pharm. Soc. Jpn. 1943, 63, 296) and metal complexes of NHC ...
... Then, N-‐heterocyclic carbenes (NHCs) already seen. The first applica4ons of thiazolydenes in umpolung organocatalysis were reported as early as 1943 (J. Pharm. Soc. Jpn. 1943, 63, 296) and metal complexes of NHC ...
Arenes HW
... the mass of phenol that is needed to produce the annual UK output of 3500 tonnes of salicylic acid. Mr of phenol = 94.0; 1 tonne = 106 g ...
... the mass of phenol that is needed to produce the annual UK output of 3500 tonnes of salicylic acid. Mr of phenol = 94.0; 1 tonne = 106 g ...
Chromatography Spectroscopy HW
... the mass of phenol that is needed to produce the annual UK output of 3500 tonnes of salicylic acid. Mr of phenol = 94.0; 1 tonne = 106 g ...
... the mass of phenol that is needed to produce the annual UK output of 3500 tonnes of salicylic acid. Mr of phenol = 94.0; 1 tonne = 106 g ...
Exam 3 - Chemistry
... states for the rate limiting step and any reactive intermediates; identify the rate limiting step. O ...
... states for the rate limiting step and any reactive intermediates; identify the rate limiting step. O ...
16.7 Addition of Alcohols: Hemiacetals and Acetals
... • A major exception occurs when the C=O and -OH functional groups that react are part of the same molecule. The resulting cyclic hemiacetal is more stable than a noncyclic hemiacetal. • Most simple sugars exist mainly in the cyclic hemiacetal form, as shown below for glucose, rather than in the ope ...
... • A major exception occurs when the C=O and -OH functional groups that react are part of the same molecule. The resulting cyclic hemiacetal is more stable than a noncyclic hemiacetal. • Most simple sugars exist mainly in the cyclic hemiacetal form, as shown below for glucose, rather than in the ope ...
EXPERIMENT 5: Oxidation of Alcohols: Solid
... Na2Cr2O7) to an aqueous acidic solution. The reactions in both methods are called chromate or chromic acid oxidation. H 2O ...
... Na2Cr2O7) to an aqueous acidic solution. The reactions in both methods are called chromate or chromic acid oxidation. H 2O ...
Wolff rearrangement
The Wolff rearrangement is a reaction in organic chemistry in which an α-diazocarbonyl compound is converted into a ketene by loss of dinitrogen with accompanying 1,2-rearrangement. The Wolff rearrangement yields a ketene as an intermediate product, which can undergo nucleophilic attack with weakly acidic nucleophiles such as water, alcohols, and amines, to generate carboxylic acid derivatives or undergo [2+2] cycloaddition reactions to form four-membered rings. The mechanism of the Wolff rearrangement has been the subject of debate since its first use. No single mechanism sufficiently describes the reaction, and there are often competing concerted and carbene-mediated pathways; for simplicity, only the textbook, concerted mechanism is shown below. The reaction was discovered by Ludwig Wolff in 1902. The Wolff rearrangement has great synthetic utility due to the accessibility of α-diazocarbonyl compounds, variety of reactions from the ketene intermediate, and stereochemical retention of the migrating group. However, the Wolff rearrangement has limitations due to the highly reactive nature of α-diazocarbonyl compounds, which can undergo a variety of competing reactions.The Wolff rearrangement can be induced via thermolysis, photolysis, or transition metal catalysis. In this last case, the reaction is sensitive to the transition metal; silver (I) oxide or other Ag(I) catalysts work well and are generally used. The Wolff rearrangement has been used in many total syntheses; the most common use is trapping the ketene intermediate with nucleophiles to form carboxylic acid derivatives. The Arndt-Eistert homologation is a specific example of this use, wherein a carboxylic acid may be elongated by a methylene unit. Another common use is in ring-contraction methods; if the α-diazo ketone is cyclic, the Wolff rearrangement results in a ring-contracted product. The Wolff rearrangement works well in generating ring-strained systems, where other reactions may fail.