In step I the alpha bromination of ketones is acid catalyzed.
1. In step I the alpha bromination of ketones is acid catalyzed.
a. What acid is formed as Step 1 progresses?
b. Why are alpha bromination reactions acid catalyzed?
2. Substitution of bromine by t-butyl amine is the second step of the reaction today. Secondary alkyl halides can undergo substitution by Sn1 or Sn2 mechanisms. Explain (in terms of electronic interactions) why an Sn2 mechanism is favored when the halogen is alpha to a carbonyl. (Hint: Like charges on adjacent atoms are unfavorable)
Homework Answers
1.
(a)
During acid catalyzed alpha-bromination of ketone, as the step-1 progress HBr is formed.
(b)
During alpha-bromination, H+ reacts with O - atom attached to carbonyl carbon and forms enol. The -C=C- double bond in enol is reactive and reacts with Br2 to form alpha-brominated ketone and HBr.
Hence the reaction is acid catalyzed.
Substitution of bromine by t-butyl amine is the second step of the reaction today.
2. Substitution of bromine by t-butyl amine is the second step of the reaction today. Secondary alkyl halides can undergo substitution by Sn1 or Sn2 mechanisms. Explain (in terms of electronic interactions) why an Sn2 mechanism is more favored in this case when the bromide is alpha to a carbonyl. 3. Based on your answer in 2. select the most likely reaction pathway. Explain how the substitution mechanism forms the product structure(s) shown.
3. Based on your answer in 2. select the most likely reaction pathway. Explain how the...
3. Based on your answer in 2. select the most likely reaction pathway. Explain how the substitution mechanism forms the product structure(s) shown. 2points А, H Br off and add NH toi O position because it Would Rick Ph Ph Ph- B H NH2 Ph Ph + NH 4. Identify the reaction components and solvents as more soluble in the aqueous (A) or organic (O) layer during separation of substitution and protonation steps. 3 pts Br HN НN CIO NH3...
In the mechanism of the acid-catalyzed halogenation of ketones, which of the following is NOT true?...
In the mechanism of the acid-catalyzed halogenation of ketones, which of the following is NOT true? Select one A. The rate-determining step is the attachment of a halogen atom to an enol intermediate. O B. The first step is attachment of Ht to the carbonyl oxygern. O C. The reaction rate is independent of the halogen (X2) concentration D. The rate-determining step is the loss of an H* from an alpha- carbon to form an enol intermediate
What is the organic product In the mechanism of the acid-catalyzed halogenation of ketones, which of...
What is the organic product In the mechanism of the acid-catalyzed halogenation of ketones, which of the following is NOT true? A. The rate-determining step is the attachment of a halogen atom to an enol intermediate B. The first step is attachment of H^+ to the carbonyl oxygen. C. The reaction rate is independent of the halogen (X_2) concentration. D. The rate-determining step is the loss of an H^+ from an alpha-carbon to form an enol Intermediate.
5) Iodine is a better leaving group than bromine. But iodine is a better nucleophile than bromine. Why is that? Introdu...
5) Iodine is a better leaving group than bromine. But iodine is
a better nucleophile than bromine. Why is that?
Introduction Alkyl halides can be prepared from alcohols by reactions with hydrogen halides (HCI, HBr, or HI) via nucleophilic substitution. In this type of reaction, the nucleophile displaces a leaving group from a carbon atom of an organic substrate (here the alcohol once protonated). Both electrons of the new bond to the carbon are provided by the nucleophile while the...
1) State which of the electrophiles given below will react preferentially by i) SN1, ii) by...
1) State which of the electrophiles given below will react
preferentially by i) SN1, ii) by SN2, or iii) capable of reacting
by either of the two mechanisms depending on the given conditions.
How can you affect those conditions to favour SN1 or SN2? Reason
your predictions based on the structures of the compounds. Br-CH3,
Br-CH2CH3, Br-CH(CH3)2, Br-C(CH3)3, Br-CH2-C5H6; C5H6 = phenyl
Introduction Alkyl halides can be prepared from alcohols by reactions with hydrogen halides (HCI, HBr, or HI) via...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic, unimolecular) and S2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Snl route, primary alcohols follow the S2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Sul reaction involves rapid protonation of the alcohol, followed by the...
1. Write the OVERALL reaction for this lab. 2. Show the mechanism's steps for this reaction....
1. Write the OVERALL reaction for this lab. 2. Show the mechanism's steps for this reaction. Be sure to include the arrows showing where the electrons are being transferred. 3. What is(are) the intermediates in this mechanism? 4. Which step is the rate determining step? 13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic,...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic, unimolecular) and S2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Snl route, primary alcohols follow the S2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Sul reaction involves rapid protonation of the alcohol, followed by the...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as SNI (substitution, nucleophilic, unimolecular) and S 2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Syl route, primary alcohols follow the Sy2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Syl reaction involves rapid protonation of the alcohol, followed by...
3. Based on your answer in 2. select the most likely reaction pathway. Explain how the substitution mechanism forms the product structure(s) shown. 2points А, H Br off and add NH toi O position because it Would Rick Ph Ph Ph- B H NH2 Ph Ph + NH 4. Identify the reaction components and solvents as more soluble in the aqueous (A) or organic (O) layer during separation of substitution and protonation steps. 3 pts Br HN НN CIO NH3...
In the mechanism of the acid-catalyzed halogenation of ketones, which of the following is NOT true? Select one A. The rate-determining step is the attachment of a halogen atom to an enol intermediate. O B. The first step is attachment of Ht to the carbonyl oxygern. O C. The reaction rate is independent of the halogen (X2) concentration D. The rate-determining step is the loss of an H* from an alpha- carbon to form an enol intermediate
What is the organic product In the mechanism of the acid-catalyzed halogenation of ketones, which of the following is NOT true? A. The rate-determining step is the attachment of a halogen atom to an enol intermediate B. The first step is attachment of H^+ to the carbonyl oxygen. C. The reaction rate is independent of the halogen (X_2) concentration. D. The rate-determining step is the loss of an H^+ from an alpha-carbon to form an enol Intermediate.
5) Iodine is a better leaving group than bromine. But iodine is
a better nucleophile than bromine. Why is that?
Introduction Alkyl halides can be prepared from alcohols by reactions with hydrogen halides (HCI, HBr, or HI) via nucleophilic substitution. In this type of reaction, the nucleophile displaces a leaving group from a carbon atom of an organic substrate (here the alcohol once protonated). Both electrons of the new bond to the carbon are provided by the nucleophile while the...
1) State which of the electrophiles given below will react
preferentially by i) SN1, ii) by SN2, or iii) capable of reacting
by either of the two mechanisms depending on the given conditions.
How can you affect those conditions to favour SN1 or SN2? Reason
your predictions based on the structures of the compounds. Br-CH3,
Br-CH2CH3, Br-CH(CH3)2, Br-C(CH3)3, Br-CH2-C5H6; C5H6 = phenyl
Introduction Alkyl halides can be prepared from alcohols by reactions with hydrogen halides (HCI, HBr, or HI) via...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic, unimolecular) and S2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Snl route, primary alcohols follow the S2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Sul reaction involves rapid protonation of the alcohol, followed by the...
1. Write the OVERALL reaction for this lab. 2. Show the mechanism's steps for this reaction. Be sure to include the arrows showing where the electrons are being transferred. 3. What is(are) the intermediates in this mechanism? 4. Which step is the rate determining step? 13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic,...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as Syl (substitution, nucleophilic, unimolecular) and S2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Snl route, primary alcohols follow the S2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Sul reaction involves rapid protonation of the alcohol, followed by the...
13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as SNI (substitution, nucleophilic, unimolecular) and S 2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Syl route, primary alcohols follow the Sy2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Syl reaction involves rapid protonation of the alcohol, followed by...
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