Chapter 18 lectures as pdf
... This chapter • Less basic sources of nucleophilic carbon • Formation of C-C bonds but some chance of reversibility • Strategies for control of reversibility • Use in synthesis • Related reactions ...
... This chapter • Less basic sources of nucleophilic carbon • Formation of C-C bonds but some chance of reversibility • Strategies for control of reversibility • Use in synthesis • Related reactions ...
Document
... 4) Cool the reaction mixture to room temperature. Transfer the mixture into a 125 mL separatory funnel and add cold water (25 mL). Extract and separate the aqueous layer. 5) Wash the organic layer twice with 5% NaHCO3 (25 mL each time). 6) Wash the organic layer with saturated NaCl solution (25 mL). ...
... 4) Cool the reaction mixture to room temperature. Transfer the mixture into a 125 mL separatory funnel and add cold water (25 mL). Extract and separate the aqueous layer. 5) Wash the organic layer twice with 5% NaHCO3 (25 mL each time). 6) Wash the organic layer with saturated NaCl solution (25 mL). ...
Carbonyl The carbonyl function, C=O, exists in a number of organic
... Reactions of RXC=O groups; Acid, ester, acid halide, anhydride, amide The characteristic reaction of this class of carbonyl compounds is the first step of addition of the nucleophile followed by elimination of the X function to give the final product. In acid catalysis the carbonyl is first protonat ...
... Reactions of RXC=O groups; Acid, ester, acid halide, anhydride, amide The characteristic reaction of this class of carbonyl compounds is the first step of addition of the nucleophile followed by elimination of the X function to give the final product. In acid catalysis the carbonyl is first protonat ...
Chapter 17: Aldehydes and Ketones: Nucleophilic Addition to the
... The Wittig reaction is highly selective for ketones and aldehydes; esters, lactones, nitriles and amides will not react but are tolerated in the substrate. Acidic groups (alcohols, amine and carboxylic acids) are not tolerated. O O ...
... The Wittig reaction is highly selective for ketones and aldehydes; esters, lactones, nitriles and amides will not react but are tolerated in the substrate. Acidic groups (alcohols, amine and carboxylic acids) are not tolerated. O O ...
Lecture 11a
... • Other considerations • Despite the addition of the catalyst, the rate of the reaction is still very low at room temperature • Reflux the mixture to increase the rate of the reaction ...
... • Other considerations • Despite the addition of the catalyst, the rate of the reaction is still very low at room temperature • Reflux the mixture to increase the rate of the reaction ...
H1- Functional Groups Theory Sheet Alcohol An alcohol group
... The previous examples are all aliphatic (or alkyl), meaning that they are not attached to a benzene or arene/aryl ring. If these functional groups are attached to a benzene/arene ring they are known as aromatic. In the green box below, there are examples of specific aromatic functional groups. ...
... The previous examples are all aliphatic (or alkyl), meaning that they are not attached to a benzene or arene/aryl ring. If these functional groups are attached to a benzene/arene ring they are known as aromatic. In the green box below, there are examples of specific aromatic functional groups. ...
The carbonyl group
... nitrogen containing compounds through nucleophilic addition and subsequent loss of water to give products that have a carbon nitrogen double bond. These reactions are useful in distinguishing an aldehyde or ketone from other functional groups. (General test) ...
... nitrogen containing compounds through nucleophilic addition and subsequent loss of water to give products that have a carbon nitrogen double bond. These reactions are useful in distinguishing an aldehyde or ketone from other functional groups. (General test) ...
Reactions to know from Chapters 17, 18, 19
... Starting with either an aldehyde or a ketone, you can see that the hemiacetals formed are characterized by having a carbon bonded to an OH- group and an OR- group. Here, the oxygen of the alcohol attacks and bonds with the carbonyl carbon of the aldehyde or ketone If the alcohol group and the ...
... Starting with either an aldehyde or a ketone, you can see that the hemiacetals formed are characterized by having a carbon bonded to an OH- group and an OR- group. Here, the oxygen of the alcohol attacks and bonds with the carbonyl carbon of the aldehyde or ketone If the alcohol group and the ...
Summary of Reactions Which Will Appear on Exams
... 42. REACTIONS OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS WITH ESTERS TO FORM TERTIARY ALCOHOLS ...
... 42. REACTIONS OF GRIGNARD REAGENTS AND ORGANOLITHIUM COMPOUNDS WITH ESTERS TO FORM TERTIARY ALCOHOLS ...
06_reactions
... aldehyde + Tollens’ reagent → carboxylate anion + silver metal + ammonia (there will be more reactants or products depending on half-reactions) Example: methanal + Tollens’ reagent → methanoic acid + silver + ammonia CH2O + Ag(NH3)2+ + H2O → CHOOH + Ag + 2NH3 + 2H+ Since an obvious silver ‘mirror’ f ...
... aldehyde + Tollens’ reagent → carboxylate anion + silver metal + ammonia (there will be more reactants or products depending on half-reactions) Example: methanal + Tollens’ reagent → methanoic acid + silver + ammonia CH2O + Ag(NH3)2+ + H2O → CHOOH + Ag + 2NH3 + 2H+ Since an obvious silver ‘mirror’ f ...
today`s PowerPoint
... • You can use 2,4 – dinitrophenylhydrazine or 2,4-DNP to test for the carbonyl group. • A solution of 2,4-DNP, methanol and H2SO4 is known as Brady’s reagent. • A positive test will give an orange/yellow precipitate. • Both aldehydes and ketones will test positively. No other compounds (e.g. Carboxy ...
... • You can use 2,4 – dinitrophenylhydrazine or 2,4-DNP to test for the carbonyl group. • A solution of 2,4-DNP, methanol and H2SO4 is known as Brady’s reagent. • A positive test will give an orange/yellow precipitate. • Both aldehydes and ketones will test positively. No other compounds (e.g. Carboxy ...
Chapter 1 Structure and Bonding
... Nucleophile approaches, causing C to rehybridize p-bond electrons move to Oxygen, producing an alkoxide anion Protonation from solvent yields the product The new Nu—C bond has both electrons from Nu- (like in SN2) An electron pair is the “leaving group” Strongly basic nucleophiles typically follow t ...
... Nucleophile approaches, causing C to rehybridize p-bond electrons move to Oxygen, producing an alkoxide anion Protonation from solvent yields the product The new Nu—C bond has both electrons from Nu- (like in SN2) An electron pair is the “leaving group” Strongly basic nucleophiles typically follow t ...
10.6 Carboxylic Acids Learning Outcomes (a) describe the formation
... The nitrile is heated under reflux with a dilute acid such as dilute hydrochloric acid. A carboxylic acid is formed. For example, starting from ethanenitrile you would get ethanoic acid. The ethanoic acid could be distilled off the mixture. ...
... The nitrile is heated under reflux with a dilute acid such as dilute hydrochloric acid. A carboxylic acid is formed. For example, starting from ethanenitrile you would get ethanoic acid. The ethanoic acid could be distilled off the mixture. ...
C h e m g u id e –... ESTERS: PREPARATION
... d) If you want to prepare some ethyl ethanoate on a larger scale, you would heat the reaction mixture in a flask and distil off and collect the ester as it is formed. Why does this work effectively for the small esters? 2. a) You can also make esters by reacting an acyl chloride with an alcohol. Wri ...
... d) If you want to prepare some ethyl ethanoate on a larger scale, you would heat the reaction mixture in a flask and distil off and collect the ester as it is formed. Why does this work effectively for the small esters? 2. a) You can also make esters by reacting an acyl chloride with an alcohol. Wri ...
Aldehid dan Keton
... • More polar, so higher boiling point than comparable alkane or ether. • Cannot H-bond to each other, so lower boiling point than comparable alcohol. ...
... • More polar, so higher boiling point than comparable alkane or ether. • Cannot H-bond to each other, so lower boiling point than comparable alcohol. ...
Discuss on Reactions of Alcohols
... decrease in acidity is due to two factors: an increase of electron density on the oxygen atom of the more highly‐substituted alcohol, and steric hindrance (because of the alkyl groups, which inhibit solvation of the resulting alkoxide ion). Both of these situations increase the activation energy for ...
... decrease in acidity is due to two factors: an increase of electron density on the oxygen atom of the more highly‐substituted alcohol, and steric hindrance (because of the alkyl groups, which inhibit solvation of the resulting alkoxide ion). Both of these situations increase the activation energy for ...
CHM412 June 2013 paper
... the strong hydrogen bonds), then molecuels with dipoles which have lower bpt’s followed by (non-polar) molecules with LDF’s only. Within the H-bonding species, Carboxylic acids form dimers (as part d) mentions), that is, two sets of Hbonding to one other molecule, so their H-bonds are stronger than ...
... the strong hydrogen bonds), then molecuels with dipoles which have lower bpt’s followed by (non-polar) molecules with LDF’s only. Within the H-bonding species, Carboxylic acids form dimers (as part d) mentions), that is, two sets of Hbonding to one other molecule, so their H-bonds are stronger than ...
Chapter 7
... • The slow step, RDS, is the second step, the formation of the carbocation • This explains the order of reactivity with the tertiary alcohol reacting easiest, due to the tertiary carbocation being the most stable. ...
... • The slow step, RDS, is the second step, the formation of the carbocation • This explains the order of reactivity with the tertiary alcohol reacting easiest, due to the tertiary carbocation being the most stable. ...
Chemdraw B&W - Pennsylvania State University
... • The conjugate base of a ketone or aldehyde is an enolate ion - the negative charge is delocalized onto oxygen ...
... • The conjugate base of a ketone or aldehyde is an enolate ion - the negative charge is delocalized onto oxygen ...
CN>Chapter 22CT>Carbonyl Alpha
... Intramolecular a-alkylation in the Favorskii rearrangement proceeds via enolate anion generated within the molecule. The molecule must contain a leaving group, usually a halide. The purpose of the reaction is two fold: 1. Molecular rearrangements of ketones to carboxylic acids and 2. Ring contractio ...
... Intramolecular a-alkylation in the Favorskii rearrangement proceeds via enolate anion generated within the molecule. The molecule must contain a leaving group, usually a halide. The purpose of the reaction is two fold: 1. Molecular rearrangements of ketones to carboxylic acids and 2. Ring contractio ...
Qualitative Analysis II Notes
... Application and History It is only within the last 50 years that a chemist may take and unknown sample and obtain an IR, 1H NMR, 13C NMR, and within a short amount of time know the class of compound if not the exact chemical structure of the material. Analytical instrumentation is very expensive. Ma ...
... Application and History It is only within the last 50 years that a chemist may take and unknown sample and obtain an IR, 1H NMR, 13C NMR, and within a short amount of time know the class of compound if not the exact chemical structure of the material. Analytical instrumentation is very expensive. Ma ...
organic revision nots
... 22. Carboxylic acids are higher boiling liquids than aldehydes, ketones and even alcohols of comparable molecular masses. 23. Aliphatic carboxylic acids having upto four carbon atoms are miscible in water 24. During the preparation of esters from a carboxylic acid and an alcohol in the presence of a ...
... 22. Carboxylic acids are higher boiling liquids than aldehydes, ketones and even alcohols of comparable molecular masses. 23. Aliphatic carboxylic acids having upto four carbon atoms are miscible in water 24. During the preparation of esters from a carboxylic acid and an alcohol in the presence of a ...
06 MC /08 MC /08 NMR
... Counting this cover sheet, there are a total of 9 pages- check to ensure you have all 9. All 9 pages must be turned in for grading. Use the backside of preceding pages for scratch paper. Any cheating will result in the dismissal from c/ass with an "F" grade. Please put your name or initial on each p ...
... Counting this cover sheet, there are a total of 9 pages- check to ensure you have all 9. All 9 pages must be turned in for grading. Use the backside of preceding pages for scratch paper. Any cheating will result in the dismissal from c/ass with an "F" grade. Please put your name or initial on each p ...
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.