organic chemistry ii
... Aldehydes and ketones which possess -hydrogens can undergo enolization. Most enols are unstable and reactive and instantly equilibrate to the “keto” form. Certain enols, such as -dicarbonyl compounds, among others, are exceptionally stable. Under basic conditions aldehydes and ketones form enolate ...
... Aldehydes and ketones which possess -hydrogens can undergo enolization. Most enols are unstable and reactive and instantly equilibrate to the “keto” form. Certain enols, such as -dicarbonyl compounds, among others, are exceptionally stable. Under basic conditions aldehydes and ketones form enolate ...
Exam 2 Review A
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
Organic Reactions 2.1- 2.3 - mccormack-sch4u-2013
... • Carbon atom forms fewer bonds to Oxygen or more bonds to Hydrogen • Aldehydes, ketones and carboxyliic acids can be “reduced” to alcohols • Alkenes and alkynes can be reduced to become alkanes • Occurs in the presence of reducing agents such as LiAlH4, and H2 where Hydrogen [H] is added ...
... • Carbon atom forms fewer bonds to Oxygen or more bonds to Hydrogen • Aldehydes, ketones and carboxyliic acids can be “reduced” to alcohols • Alkenes and alkynes can be reduced to become alkanes • Occurs in the presence of reducing agents such as LiAlH4, and H2 where Hydrogen [H] is added ...
Exam 2 Review A
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
Microsoft Word - Final Exam Study Guide
... stability, elimination reactions, Zaitsev’s rule, E1 mechanism, E2 mechanism, antiperiplanar, comparing substitution and elimination mechanisms, synthesis of ethers, alcohols, and epoxides, dehydration of alcohols, carbocation rearrangements, reactions of alcohols/ethers/epoxides, multistep synthesi ...
... stability, elimination reactions, Zaitsev’s rule, E1 mechanism, E2 mechanism, antiperiplanar, comparing substitution and elimination mechanisms, synthesis of ethers, alcohols, and epoxides, dehydration of alcohols, carbocation rearrangements, reactions of alcohols/ethers/epoxides, multistep synthesi ...
a. Rank by acidity. The most acidic compound is 1, wh
... Why does one glycol not react with periodic acid? (6 points) In the second reaction a trans stereochemistry is obtained for the glycol. The periodate cannot form with a trans stereochemistry of the two alcohols. 3.(8) Consider the reaction shown. Indicate a mechanism, by showing intermediates obtain ...
... Why does one glycol not react with periodic acid? (6 points) In the second reaction a trans stereochemistry is obtained for the glycol. The periodate cannot form with a trans stereochemistry of the two alcohols. 3.(8) Consider the reaction shown. Indicate a mechanism, by showing intermediates obtain ...
LOYOLA COLLEGE (AUTONOMOUS), CHENNAI – 600 034 PART-A
... Dehydrobromintion of threo-1-bromo-1,2-diphenylpropane is faster than erythro. Explain. ‘Aryldiazonium salt involves both in electrophilic and nucleophilic substitutions’. Justify. What is first order asymmetric transformation? Give an example. How do inductive and field effects affect the second su ...
... Dehydrobromintion of threo-1-bromo-1,2-diphenylpropane is faster than erythro. Explain. ‘Aryldiazonium salt involves both in electrophilic and nucleophilic substitutions’. Justify. What is first order asymmetric transformation? Give an example. How do inductive and field effects affect the second su ...
C h e m g u id e –... ACID ANHYDRIDES: INTRODUCTION
... 1. a) van der Waals dispersion forces and dipole-dipole interactions. b) It reacts with moisture in the air or your nose to produce ethanoic acid. c) Ethanoic anhydride reacts with water and doesn’t simply dissolve in it. 2. Ethanoyl chloride reacts with molecules containing a hydrogen atom attached ...
... 1. a) van der Waals dispersion forces and dipole-dipole interactions. b) It reacts with moisture in the air or your nose to produce ethanoic acid. c) Ethanoic anhydride reacts with water and doesn’t simply dissolve in it. 2. Ethanoyl chloride reacts with molecules containing a hydrogen atom attached ...
Chem 400 Review Chem 350 JJ.S17
... Electron withdrawing substituents stabilize conjugate bases while electron donating ones destabilize a conjugate base Alcohols preparation: via SN1, SN2, hydration, and Grignard (MgBr-[C…]) mechanisms Reduction: H2 with Pt/Pd, NaBH4 and LiAlH4 (more reactive, can be used for esters). Need quen ...
... Electron withdrawing substituents stabilize conjugate bases while electron donating ones destabilize a conjugate base Alcohols preparation: via SN1, SN2, hydration, and Grignard (MgBr-[C…]) mechanisms Reduction: H2 with Pt/Pd, NaBH4 and LiAlH4 (more reactive, can be used for esters). Need quen ...
chapter 2: reactions of organic compounds
... • Carbon atom forms fewer bonds to Oxygen or more bonds to Hydrogen • Aldehydes, ketones and carboxyliic acids can be “reduced” to alcohols • Alkenes and alkynes can be reduced to become alkanes • Occurs in the presence of reducing agents such as LiAlH4, and H2 where Hydrogen [H] is added ...
... • Carbon atom forms fewer bonds to Oxygen or more bonds to Hydrogen • Aldehydes, ketones and carboxyliic acids can be “reduced” to alcohols • Alkenes and alkynes can be reduced to become alkanes • Occurs in the presence of reducing agents such as LiAlH4, and H2 where Hydrogen [H] is added ...
Exam 2 Review A
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
... three things: 1. React with nucleophiles, 2. -eliminate (lose H+) to form an alkene, 3. undergo skeletal rearrangements via 1,2-hydride shifts or 1,2-methanide shifts. [we will defer discussion of #3 until Chapter 7]. Remember, carbocation stability plays a role in analyzing transition states, whic ...
Unit 4_Carbonyl and carboxylic acid questions
... 4. Explain in terms of bonding why carbonyls have higher b.ps than corresponding alkanes but lower b.ps than corresponding alcohols. ...
... 4. Explain in terms of bonding why carbonyls have higher b.ps than corresponding alkanes but lower b.ps than corresponding alcohols. ...
Chapter 7: Structure and Synthesis of Alkenes
... Ú Alkenes are hydrocarbons with C=C in their structure. They are also known as “olefins”. Ú We have already covered the basics of alkenes nomenclature, but here are a few important groups with common names that you can use as well. ...
... Ú Alkenes are hydrocarbons with C=C in their structure. They are also known as “olefins”. Ú We have already covered the basics of alkenes nomenclature, but here are a few important groups with common names that you can use as well. ...
+ Y
... has an electron-poor atom (e.g H+, CH3+ ) and can form a bond by accepting a pair of electrons from a nucleophile ...
... has an electron-poor atom (e.g H+, CH3+ ) and can form a bond by accepting a pair of electrons from a nucleophile ...
Microsoft Word - Final Exam Study Guide
... synthesis of ethers, alcohols, and epoxides, dehydration of alcohols, carbocation rearrangements, reactions of alcohols/ethers/epoxides, multistep synthesis, protecting groups, redox reactions, reagents for redox reactions, Grignard reaction ...
... synthesis of ethers, alcohols, and epoxides, dehydration of alcohols, carbocation rearrangements, reactions of alcohols/ethers/epoxides, multistep synthesis, protecting groups, redox reactions, reagents for redox reactions, Grignard reaction ...
Chapter 1 Chemical Bonding and Chemical Structure
... Acylation of Amines • Amines can be converted into amides by reaction with acid chlorides, anhydrides, or esters. ...
... Acylation of Amines • Amines can be converted into amides by reaction with acid chlorides, anhydrides, or esters. ...
CHMY_271_practice_exam_3
... 11. (6 pt) If the following alkyl halide were to undergo elimination, predict the major product in each case, and explain your answer. You do not need to draw out the mechanism, but knowing the mechanism will help you to predict reasonable products. Br ...
... 11. (6 pt) If the following alkyl halide were to undergo elimination, predict the major product in each case, and explain your answer. You do not need to draw out the mechanism, but knowing the mechanism will help you to predict reasonable products. Br ...
solutions
... A1) What factor determines the order of water-solubility for a series of substances? a) intermolecular forces b) intramolecular forces c) boiling points d) molecular shape A2) Which of the following molecules will not undergo oxidation? a) 2-propanol b) 2-methylpropanal c) 2-methyl-2-butanol ...
... A1) What factor determines the order of water-solubility for a series of substances? a) intermolecular forces b) intramolecular forces c) boiling points d) molecular shape A2) Which of the following molecules will not undergo oxidation? a) 2-propanol b) 2-methylpropanal c) 2-methyl-2-butanol ...
aldehyde ketone
... CH3-CH2-OH CH3-CHO + 2H+ + 2e CH3-CHO + H2O CH3COOH + 2H+ + 2e reduction; Cr2O72-(aq) + 14H+(aq) + 6e- 2Cr3+ (aq) +7H2O orange ...
... CH3-CH2-OH CH3-CHO + 2H+ + 2e CH3-CHO + H2O CH3COOH + 2H+ + 2e reduction; Cr2O72-(aq) + 14H+(aq) + 6e- 2Cr3+ (aq) +7H2O orange ...
CHEM1102 Worksheet 7: Reactions of Carbonyls and Acid
... Grignard reagents (RMgBr) are excellent nucleophiles, and are a very good way to form new carbon-carbon bonds. ...
... Grignard reagents (RMgBr) are excellent nucleophiles, and are a very good way to form new carbon-carbon bonds. ...
Handout 7
... In conclusion, all steps included in the conversion of an aldehyde or ketone to acetal or ketal via hemiacetal or hemiketal as intermediates, are reversible. Performing the reaction in large excess of an anhydrous alcohol and a small amount of an anhydrous acid will strongly favour the formation of ...
... In conclusion, all steps included in the conversion of an aldehyde or ketone to acetal or ketal via hemiacetal or hemiketal as intermediates, are reversible. Performing the reaction in large excess of an anhydrous alcohol and a small amount of an anhydrous acid will strongly favour the formation of ...
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.