what base can be used to completely deprotonate the alpha proton of a ketone? A.(CH3)3COK B.CH3ONa...
what base can be used to completely deprotonate the alpha proton of a ketone? A.(CH3)3COK B.CH3ONa C.LDA D.NaOH
Homework Answers
answer:
c ) LDA
Lithium diisopropyl amide (LDA) is commonly used to generate enolates. Diisopropylamine has a pKa of 40, so it can completely deprotonate carbonyls (pKa 20- 25).
The crossed aldol can then be done by treating one carbonyl compound with one equivalent of LDA. •
The enolate that is formed can then be reacted with a carbonyl electrophile, such as an aldehyde or ester.
Protonation is done in a second step, since the LDA reaction is not in the presence of a protic solvent.
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what base can be used to completely deprotonate the alpha proton
of a ketone? A.(CH3)3COK B.CH3ONa...
What bases are commonly used to deprotonate alpha carbons
What bases are commonly used to deprotonate alpha carbons
Question 4 The base used to deprotonate diethyl malonate is always ethoxide. The base should be...
Question 4 The base used to deprotonate diethyl malonate is always ethoxide. The base should be the same as the leaving group on the ester. What would happen if hydroxide was used instead? O Nothing, hydroxide is not a strong enough base to deprotonate diethyl malonate O Hydroxide could also act as a nucleophile and do a saponification reaction on the ester O The decarboxylation step would not work with hydroxide Question 5
Our instructor said that if the pKa is >16 a reagent should completely deprotonate an alkylthiol....
Our instructor said that if the pKa is >16 a reagent should
completely deprotonate an alkylthiol. But he also said the pKa
difference has to be at least 5, preferably 10, to completely
deprotonate.
I'm not sure what pKa to use for some of these since they're
sodium based-NaCN in particular. (And the pKa for a generic
alkylthiol.
I think these are right:
H20=15.8 so no.
NH3=38 so yes
NaNH2=38 so yes
NaO2CCH3=24 so yes (?) its the conjugate base...
Preparation of and alpha, beta-unsaturated ketone via Michael and Aldol Condensation
Preparation of and alpha, beta-unsaturated ketone via Michael and Aldol Condensation: 6-ethoxycarbonyl-3,5-diphenyl-2-cyclohexanone.Draw a mechanism for each of the three steps in the preparation of 6-ethoxycarbonyl-3,5-diphenyl-2-cyclohexenone. You may assume that NaOH functions as a base andethanol serves as a proton source
please explain your answers 3. Circle the stronger base in each pair. (0.2 pts ea = 2.0 pts) a. (CH3) 3COK vs. CH3O...
please explain your answers
3. Circle the stronger base in each pair. (0.2 pts ea = 2.0 pts) a. (CH3) 3COK vs. CH3OK b. HCECNa vs. CH3CH2ONa c. NaNH2 vs. HCECNA d. NaCN vs. NaI e. NAHCO3 vs. NaOH f. NaOH vs. C6H5CO2Na g. C6H5CO2Na vs. C6H5ONa h. CH3CO2Na vs. CH3ONa i. CH3ONa vs. NaH j. NH3 vs. CH3CO2Na
OH to CH3 R R CEN сн. For reaction of an aldehyde or ketone to form...
OH to CH3 R R CEN сн. For reaction of an aldehyde or ketone to form a cyanohydrin (section 21.9 of the textbook), which of the following statements are true? Select all correct answers. The yield of this reaction is typically high. This can be carried out by reaction of "CN followed by aqueous workup (H*/H20). This can be carried out by reaction of the ketone with HCN. The product reverses back to starting materials upon treatment with base. The...
2. Synthesis of 1-hexanol. a) Suggest one base that can deprotonate 1-butyne. b) When the deprotonated...
2. Synthesis of 1-hexanol. a) Suggest one base that can deprotonate 1-butyne. b) When the deprotonated 1-butyne reacts with epoxyethane, CH3CH2CCCH2CH2O- forms. Draw this step's curly arrow mechanism. c) Suggest an acid that will covert CH3CH2CCCH2CH2O- to CH3CH2CCCH2CH2OH. d) What reagents are needed to convert CH3CH2CCCH2CH2OH to 1-hexanol?
Identify reaction mechanisms. 1. NaHCO3 CO2Nal CH3 CH3 2. CH3 a-Proton transfer b-Lewis acid/base c- Electrophilic...
Identify reaction mechanisms.
1. NaHCO3 CO2Nal CH3 CH3 2. CH3 a-Proton transfer b-Lewis acid/base c- Electrophilic addition f-S^1 Nucleophilic substitution g-SN2 Nucleophilic substitution d-El Elimination e E2 Eliminatior The rections above involve synthesis or reactions of alcohols and ethers Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers
please explain your answers 6. Circle all of the bases below that can be used successfully to deprotonate phenol (C...
please explain your answers
6. Circle all of the bases below that can be used successfully to deprotonate phenol (CsHsOH). (0.2 pts) a. KOH b. NHa c. NaHCO3 d. NaH
Given this information, what is the common name for this ketone? CH3CH2C(O)CH(CH3)2
Given this information, what is the common name for this ketone? CH3CH2C(O)CH(CH3)2
Question 4 The base used to deprotonate diethyl malonate is always ethoxide. The base should be the same as the leaving group on the ester. What would happen if hydroxide was used instead? O Nothing, hydroxide is not a strong enough base to deprotonate diethyl malonate O Hydroxide could also act as a nucleophile and do a saponification reaction on the ester O The decarboxylation step would not work with hydroxide Question 5
Our instructor said that if the pKa is >16 a reagent should
completely deprotonate an alkylthiol. But he also said the pKa
difference has to be at least 5, preferably 10, to completely
deprotonate.
I'm not sure what pKa to use for some of these since they're
sodium based-NaCN in particular. (And the pKa for a generic
alkylthiol.
I think these are right:
H20=15.8 so no.
NH3=38 so yes
NaNH2=38 so yes
NaO2CCH3=24 so yes (?) its the conjugate base...
please explain your answers
3. Circle the stronger base in each pair. (0.2 pts ea = 2.0 pts) a. (CH3) 3COK vs. CH3OK b. HCECNa vs. CH3CH2ONa c. NaNH2 vs. HCECNA d. NaCN vs. NaI e. NAHCO3 vs. NaOH f. NaOH vs. C6H5CO2Na g. C6H5CO2Na vs. C6H5ONa h. CH3CO2Na vs. CH3ONa i. CH3ONa vs. NaH j. NH3 vs. CH3CO2Na
OH to CH3 R R CEN сн. For reaction of an aldehyde or ketone to form a cyanohydrin (section 21.9 of the textbook), which of the following statements are true? Select all correct answers. The yield of this reaction is typically high. This can be carried out by reaction of "CN followed by aqueous workup (H*/H20). This can be carried out by reaction of the ketone with HCN. The product reverses back to starting materials upon treatment with base. The...
Identify reaction mechanisms.
1. NaHCO3 CO2Nal CH3 CH3 2. CH3 a-Proton transfer b-Lewis acid/base c- Electrophilic addition f-S^1 Nucleophilic substitution g-SN2 Nucleophilic substitution d-El Elimination e E2 Eliminatior The rections above involve synthesis or reactions of alcohols and ethers Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers
please explain your answers
6. Circle all of the bases below that can be used successfully to deprotonate phenol (CsHsOH). (0.2 pts) a. KOH b. NHa c. NaHCO3 d. NaH
Given this information, what is the common name for this ketone? CH3CH2C(O)CH(CH3)2
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