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1. Similarly to ketones, imines can be utilized as carbon nucleophiles. Draw the mechanism how imine...
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R'...
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R' / H2O+ R Nu Content Clue: Aldehydes and ketones react with various nucleophiles that can be based on carbon, hydrogen, nitrogen and oxygen. Carbon-based nucleophiles include: Grignard reagents, cyanide anion, and Wittig reagents. Grignard reagents as nucleophiles: 1) MgBr 2) H30+ 1) CH 3MgBr 2) H30+ 2 stereoisomers formed State the stereochemical relationship between products: MgBr 2. H3O+
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R'...
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R' / H2O+ R Nu Content Clue: Aldehydes and ketones react with various nucleophiles that can be based on carbon, hydrogen, nitrogen and oxygen. Carbon-based nucleophiles include: Grignard reagents, cyanide anion, and Wittig reagents. Grignard reagents as nucleophiles: 1) MgBr 2) H30+ 1) CH 3MgBr 2) H30+ 2 stereoisomers formed State the stereochemical relationship between products: MgBr 2. H3O+
1. Provide the products of the reaction below and a detailed reaction mechanism using curved arrows...
1. Provide the products of the reaction below and a detailed reaction mechanism using curved arrows to indicate the movement of electrons. (a) (b) КОН (c) Note that formation of 4- or 7-membered rings is disfavored. Hiyo KOH acidie workup 2. An interesting problem that involves a bit of review (imines and Grignard chemistry) and application of what you previously learned to a new reaction: The Carbon of an imine functional group (i.e. R.C-NR) is sufficiently electron deficient to be...
1. How would you prepare the following imine? Draw the mechanism for the imine shown below. (6points)
1. How would you prepare the following imine? Draw the mechanism for the imine shown below. (6points)
CH3 CH2 Secondary amines add to aldehydes and ketones to give enamines. Enamines are formed in...
CH3 CH2 Secondary amines add to aldehydes and ketones to give enamines. Enamines are formed in a reversible, acid-catalyzed proces nucleophilic addition of the secondary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolanine Prosonation of the hydroxyl group converts it into a good leaving group, is no Instead, a proton is lost from the neighboring carbon to form an enamine. p, however there is no hydrogen left on the nitrogen to be...
Assignment open Assignment ASSIGNMENT RESOURCES Ketones with Nucleophiles CAN Mechanism (ds) K S17 estion 1 Question...
Assignment open Assignment ASSIGNMENT RESOURCES Ketones with Nucleophiles CAN Mechanism (ds) K S17 estion 1 Question 2 uestion 3 uestion 4 uestion 5 uestion 6 uestion 7 uestion 8 uestion 9 Question 10 Review Score Review Results by Stud Objective RESET CH30H, HT heat HO O-CH CH PRINTER VERSION BACK NEXT FULL SCREEN OH OMe CH O-H HSC -O
13. What is M for 2-butanone? a) b ) 85 d) 58 O c) 72 Grignard...
13. What is M for 2-butanone? a) b ) 85 d) 58 O c) 72 Grignard reagent added to a aldehyde and H30* 14. What is the product of a Grignard reagent added to a al a) amine b) imine c) alcohol d) ketone 15. A ketal is formed from a a) amine b) imine c) alcohol d) ketone and aldehyde 16. p-Nitrobenzoic acid contains how many NO, groups? a) O b)1 c)2 d) 3 17. The carboxylic acid pentanoic...
1. Reductive amination (Carey, Section 22.10) is an important C-N bond forming strategy widely used in...
1. Reductive amination (Carey, Section 22.10) is an important C-N bond forming strategy widely used in the synthesis of biologically active natural product. It's a powerful and reliable strategy that avoids the problem of overalkylation that often accompanies direct alkylation of amines with alkyl halides (Figure 1). secondary amine r tiary amine quemary sa Figure 1: Yields are generally poor as product amines are more nucleophilic and can also react with halide. The result is often a mixture of amines...
Hydration of alkenes under aqueous acidic conditions. Draw the detailed stepwise mechanism for this reaction. Be...
Hydration of alkenes under aqueous acidic conditions. Draw the detailed stepwise mechanism for this reaction. Be sure to show all steps, intermediates, formal charges, and show the movement of electrons with curved arrows. You do not need to draw transition states. H2SO4 H20 ?? The hydration of alkynes can also occur under aqueous acidic conditions however, instead of forming the alcohol, a ketone is formed. Draw the detailed stepwise mechanism for the conversion of the alkyne to the ketone (one...
In chapter 9 we learned how to make acetylide anions and use them as nucleophiles. In...
In chapter 9 we learned how to make
acetylide anions and use them as nucleophiles. In order to use this
method, we will need to transform the alcohol to a different
functional group that would make the carbon a better electrophile.
Come up with a method (can be done in 2 steps) to produce the
desired product from cyclopentanol (6 points)
4) The following image shows the general structure of a steroid: Steroids can be utilized in the biological systems...
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R' / H2O+ R Nu Content Clue: Aldehydes and ketones react with various nucleophiles that can be based on carbon, hydrogen, nitrogen and oxygen. Carbon-based nucleophiles include: Grignard reagents, cyanide anion, and Wittig reagents. Grignard reagents as nucleophiles: 1) MgBr 2) H30+ 1) CH 3MgBr 2) H30+ 2 stereoisomers formed State the stereochemical relationship between products: MgBr 2. H3O+
Draw a general curved arrow mechanism for nucleophilic addition of aldehydes and ketones. OH Nus RA'R' / H2O+ R Nu Content Clue: Aldehydes and ketones react with various nucleophiles that can be based on carbon, hydrogen, nitrogen and oxygen. Carbon-based nucleophiles include: Grignard reagents, cyanide anion, and Wittig reagents. Grignard reagents as nucleophiles: 1) MgBr 2) H30+ 1) CH 3MgBr 2) H30+ 2 stereoisomers formed State the stereochemical relationship between products: MgBr 2. H3O+
1. Provide the products of the reaction below and a detailed reaction mechanism using curved arrows to indicate the movement of electrons. (a) (b) КОН (c) Note that formation of 4- or 7-membered rings is disfavored. Hiyo KOH acidie workup 2. An interesting problem that involves a bit of review (imines and Grignard chemistry) and application of what you previously learned to a new reaction: The Carbon of an imine functional group (i.e. R.C-NR) is sufficiently electron deficient to be...
1. How would you prepare the following imine? Draw the mechanism for the imine shown below. (6points)
CH3 CH2 Secondary amines add to aldehydes and ketones to give enamines. Enamines are formed in a reversible, acid-catalyzed proces nucleophilic addition of the secondary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolanine Prosonation of the hydroxyl group converts it into a good leaving group, is no Instead, a proton is lost from the neighboring carbon to form an enamine. p, however there is no hydrogen left on the nitrogen to be...
Assignment open Assignment ASSIGNMENT RESOURCES Ketones with Nucleophiles CAN Mechanism (ds) K S17 estion 1 Question 2 uestion 3 uestion 4 uestion 5 uestion 6 uestion 7 uestion 8 uestion 9 Question 10 Review Score Review Results by Stud Objective RESET CH30H, HT heat HO O-CH CH PRINTER VERSION BACK NEXT FULL SCREEN OH OMe CH O-H HSC -O
13. What is M for 2-butanone? a) b ) 85 d) 58 O c) 72 Grignard reagent added to a aldehyde and H30* 14. What is the product of a Grignard reagent added to a al a) amine b) imine c) alcohol d) ketone 15. A ketal is formed from a a) amine b) imine c) alcohol d) ketone and aldehyde 16. p-Nitrobenzoic acid contains how many NO, groups? a) O b)1 c)2 d) 3 17. The carboxylic acid pentanoic...
1. Reductive amination (Carey, Section 22.10) is an important C-N bond forming strategy widely used in the synthesis of biologically active natural product. It's a powerful and reliable strategy that avoids the problem of overalkylation that often accompanies direct alkylation of amines with alkyl halides (Figure 1). secondary amine r tiary amine quemary sa Figure 1: Yields are generally poor as product amines are more nucleophilic and can also react with halide. The result is often a mixture of amines...
Hydration of alkenes under aqueous acidic conditions. Draw the detailed stepwise mechanism for this reaction. Be sure to show all steps, intermediates, formal charges, and show the movement of electrons with curved arrows. You do not need to draw transition states. H2SO4 H20 ?? The hydration of alkynes can also occur under aqueous acidic conditions however, instead of forming the alcohol, a ketone is formed. Draw the detailed stepwise mechanism for the conversion of the alkyne to the ketone (one...
In chapter 9 we learned how to make
acetylide anions and use them as nucleophiles. In order to use this
method, we will need to transform the alcohol to a different
functional group that would make the carbon a better electrophile.
Come up with a method (can be done in 2 steps) to produce the
desired product from cyclopentanol (6 points)
4) The following image shows the general structure of a steroid: Steroids can be utilized in the biological systems...
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