Homework Answers
1)
Reaction A= V
Reaction B= II
2) Reaction A= 4 (No. of resonance structures)
Reaction B= 5 (No. of resonance structures).
3) Rection B will proceed faster due to higher syability of the carbocation formed due to more delocalization of possitive charge.
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Nabr (4) REVIEW: Substituents and Resonance Effects in Benzylic Carbocations. Which of these two SN1 reactions...
(4) 6 points) Benzylic Carbocations. Reaction #1 shown below illustrates the acid catalyzed electrophilic addition of...
(4) 6 points) Benzylic Carbocations. Reaction #1 shown below illustrates the acid catalyzed electrophilic addition of H20 to an alkene. This reaction goes through a Benzylic Carbocation Intermediate: HO. Reaction #1 H2SO4 - -- (a) Which one of the following structures is the most reasonable benzylic carbocation intermediate for Reaction #1? ANSWER: answer: он (A) (b) Based on your answer to (a), how many total resonance structures are there for this benzylic carbocation? ANSWER:
(2) Review of Substituent Effects: (a) For each benzylic carbocation below: (1) indicate if the substituents...
(2) Review of Substituent Effects: (a) For each benzylic carbocation below: (1) indicate if the substituents are Electron Donating (EDG). Electron Withdrawing (EWG) or Neither (N); and (11) rank these benzylic carbocations based on stability (1 -most stable and 4 - least stable) (b) For each structure below: (1) indicate if the ring substituent is Electron Donating (EDG), Electron Withdrawing (EWG) or Neither (N); (11) rank them in order of their reactivity towards EAS (1 -fast.....4-slow) a a a a
Table 1: AM1 Energies of the carbocations formed from nitration of the named compound (kcal/mol) ...
Table 1: AM1 Energies of the carbocations formed from nitration of the named compound (kcal/mol) ortho meta para Toluene (S = CH3) 221.74 224.49 219.04 Phenol (S = OH) 179.10 193.32 177.44 Trifluorotoluene (S = CF3) 95.17 90.06 93.56 Methyl benzoate (S = CO2CH3) 160.00 159.34 159.34 Using the table answer the following questions. 1 a. The carbocation intermediates are good models of the transition states for the corresponding aromatic reactions. When looking at the transition state energy of two...
4. (20 points) There are two reactions given. (Note the arrow pointing to the right and...
4. (20 points) There are two reactions given. (Note the arrow pointing to the right and the arrow pointing down => 2 reactions) Provide mechanisms for the 2 reactions. (If you need to redraw the starting material please do so). You will need to show the flow of electrons (arrow pushing), resonance structures, and intermediates. Please provide stereochemistry where necessary. Determine which reaction is Sn2 and which is Sn1. H20 OCH3 THF H2O
Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of benzyl chloride in...
Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of benzyl chloride in 2 mL of 1% AgNO3 in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 mL of 1% AgNO3 in ethanol. List the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor SN1 or SN2 mechanisms. (NOTE:...
1) Compare and contrast SN1, SN2, E1, and E2 reactions! (similarities abd differences. Requirements for each...
1) Compare and contrast SN1, SN2, E1, and E2 reactions!
(similarities abd differences. Requirements for each to
work.)
2) Why is SN2 is in direct competition with E2 while SN1 is
direct competition with E1 reaction.
3) Rate expression of each
4) which reactions are concerted? Which are atep wise?
5) which are sterospecific and what stereospecificity of each
are?
6) how do the variables below (A-D) influence reaction
pathway?
Compare and contrast SNI, SN2, El and E2 reactions. What...
Thanks 1. Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of 2-bromobutane...
Thanks
1. Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of 2-bromobutane in 2 mL of 1% AgNO, in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 ml of 1% AgNO, in ethanol. a. list the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. b. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor Sylor Sw2...
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...
Part 2 Multiple Choice. Select the best answer for each of the questions below: 1. Which...
Part 2 Multiple Choice. Select the best answer for each of the questions below: 1. Which of these molecules is not an electrophile? a) CH4 b) CH3+ c) H* d) BF3 2. Which of these molecules is not a nucleophile ? a) NH3 b) OH c) CN d) H* 3. Water behaves as: a) a nucleophile b) an electrophile c) both d) neither 4. The SN2 reaction has how many steps? a) 1 b) 2 c) 3 d) 4 5....
Please help with the question that I have circled in red. This is from a lab...
Please help with the question that I have circled in red. This
is from a lab I did and I have included the entire handout in case
it helps you to answer the question.
2015 Chem 263 2-Credit Org Lab 6T: Dehydration of Cyclohexanol to Cyclohexene Lab 6T w lecture you recently learned that alkenes undergo acid-catalyzed addition of H20 (hydration of the alkene) to yield alcohols. This lab with illustrate the same chemistry in reverse; the microscopic reverse of...
(4) 6 points) Benzylic Carbocations. Reaction #1 shown below illustrates the acid catalyzed electrophilic addition of H20 to an alkene. This reaction goes through a Benzylic Carbocation Intermediate: HO. Reaction #1 H2SO4 - -- (a) Which one of the following structures is the most reasonable benzylic carbocation intermediate for Reaction #1? ANSWER: answer: он (A) (b) Based on your answer to (a), how many total resonance structures are there for this benzylic carbocation? ANSWER:
(2) Review of Substituent Effects: (a) For each benzylic carbocation below: (1) indicate if the substituents are Electron Donating (EDG). Electron Withdrawing (EWG) or Neither (N); and (11) rank these benzylic carbocations based on stability (1 -most stable and 4 - least stable) (b) For each structure below: (1) indicate if the ring substituent is Electron Donating (EDG), Electron Withdrawing (EWG) or Neither (N); (11) rank them in order of their reactivity towards EAS (1 -fast.....4-slow) a a a a
4. (20 points) There are two reactions given. (Note the arrow pointing to the right and the arrow pointing down => 2 reactions) Provide mechanisms for the 2 reactions. (If you need to redraw the starting material please do so). You will need to show the flow of electrons (arrow pushing), resonance structures, and intermediates. Please provide stereochemistry where necessary. Determine which reaction is Sn2 and which is Sn1. H20 OCH3 THF H2O
1) Compare and contrast SN1, SN2, E1, and E2 reactions!
(similarities abd differences. Requirements for each to
work.)
2) Why is SN2 is in direct competition with E2 while SN1 is
direct competition with E1 reaction.
3) Rate expression of each
4) which reactions are concerted? Which are atep wise?
5) which are sterospecific and what stereospecificity of each
are?
6) how do the variables below (A-D) influence reaction
pathway?
Compare and contrast SNI, SN2, El and E2 reactions. What...
Thanks
1. Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of 2-bromobutane in 2 mL of 1% AgNO, in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 ml of 1% AgNO, in ethanol. a. list the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. b. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor Sylor Sw2...
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...
Part 2 Multiple Choice. Select the best answer for each of the questions below: 1. Which of these molecules is not an electrophile? a) CH4 b) CH3+ c) H* d) BF3 2. Which of these molecules is not a nucleophile ? a) NH3 b) OH c) CN d) H* 3. Water behaves as: a) a nucleophile b) an electrophile c) both d) neither 4. The SN2 reaction has how many steps? a) 1 b) 2 c) 3 d) 4 5....
Please help with the question that I have circled in red. This
is from a lab I did and I have included the entire handout in case
it helps you to answer the question.
2015 Chem 263 2-Credit Org Lab 6T: Dehydration of Cyclohexanol to Cyclohexene Lab 6T w lecture you recently learned that alkenes undergo acid-catalyzed addition of H20 (hydration of the alkene) to yield alcohols. This lab with illustrate the same chemistry in reverse; the microscopic reverse of...
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