The NMR spectrum suggests the formation of the meta-substituted product, but NH2 is an ortho/para directing group. Using the given chemicals, provide a mechanism to arrive at the meta-substituted product.
Homework Answers
Very good question.
In presence of H2SO4, protonation of aniline occurs and NH2 gets converted into NH3+.
Then NH3+is a deactivating group and directs the new incoming electrophile towards Meta position.
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The NMR spectrum suggests the formation of the
meta-substituted product, but NH2 is an ortho/para directing...
Considering 1H-NMR analysis of substituted benzenes (for ortho, para, meta nitrobromobenzene and ortho, para dinitro bromobenzene,...
Considering 1H-NMR analysis of
substituted benzenes (for ortho, para, meta nitrobromobenzene and
ortho, para dinitro bromobenzene, or meta para dinitrobromobenzene)
: What is the splitting patterns for ring hydrogens for the
substituted benzenes? Using ??3-bond and 4-bond J coupling
constants, what are: ??Relative chemical shifts of ring
hydrogens?
An NH2 substituent in an aromatic ring is: Select one: a. activating ortho-, meta- and para-directing...
An NH2 substituent in an aromatic ring is: Select one: a. activating ortho-, meta- and para-directing b. deactivating and ortho- and para-directing c. deactivating and meta-directing d. activating and meta-directing e. activating and ortho- and para-directing
15. Indicate those ortho/para director(s) and those meta director(s) - NO2 Br - -C₂Hs - NH2...
15. Indicate those ortho/para director(s) and those meta director(s) - NO2 Br - -C₂Hs - NH2 CoHs nat reagent(s), solvent(s) and chemicals are needed in making a Grignard reagent (C2HsMgBri? Choose from the following list. Water diethyl ether lithium, phenyl bromide, ethyl bromide (MR) iodine, sodium bromide, heat 17. Which one of the following reaction is a nucleophilic aromatic substitution reaction? Which one is an electrophilic aromatic substitution? HNOH,SO 18. Predict the product:
Question1: Introduction Three aromatic compounds that have ortho-para directing and activating substituents will be brominated. The...
Question1:
Introduction Three aromatic compounds that have ortho-para directing and activating substituents will be brominated. The extent of activation will be judged by the number of bromine atoms that add to the benzene ring in each case. For each of the compounds shown below you will work out if a mono- di- or tri- brominated derivative formed following treatment with acetic acid and bromine in hydrobromic acid. This will be determined by measuring the melting point and interpreting the H...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals expected in both the reactant and the product. 2) Provide the carbocation intermediate that allowed the transformation to happen at that position. 3) This molecule is (ortho, meta, para) substituted (circle one). 4) Using resonance arrows show how that carbocation can be distributed (delocalized) to multiple locations on the arene ring system. 5) Predict a different structure that can form from this delocalization. FeBrg,...
2. D type and strength of each substituents as activating(A) or outcome as ortho-para (O/P) or...
2. D type and strength of each substituents as activating(A) or outcome as ortho-para (O/P) or meta(M) directors. (6 pts) you expect an electrophile to be attached to the ring You must identify the deactivating(D) and also the expected regiochemical 3. Use aromatic, non aromatic or antiaromatic concepts to explain the reactions or molecules shown (6 pts) Provide a curved arrow mechanism to show the formation of a aromatic carbocation intermediate Show the final product H-I The pK,values for the...
1. Consider the three molecules below to answer the following questions. Circle TRUE or FALSE at...
1. Consider the three molecules below to answer the following questions. Circle TRUE or FALSE at the end of each question (0.5 points each). Molecule A Molecule C Molecule B A. The rate of EAS with Molecule B will be faster than the rate of EAS with Molecule A (assume MAJOR product formation). TRUE or FALSE B. Molecule C will undergo nitration to yield a meta-product that is the MAJOR product. TRUE or FALSE c. The rate of meta-product formation...
Examine H NMR 4. Examine the attached 'H NMR spectrum of the product from the trans-cinnamic...
Examine H NMR
4. Examine the attached 'H NMR spectrum of the product from the trans-cinnamic acid + Br (dibromide product) reaction in the lab manual. Indicate which part(s) of the dibromide product give rise to the peaks at 5 and 5.5 ppm. OS SOIT -1093.75 SEZO- ES OEDI- H Ả Br 0 " H OH Bri dibromide product 1H NMR (Note the OH is not shown) 6 84 8.2 8.0 7.8 7.6 74 7.2 70 69 6.6 6.4 6.2...
5. Examine the attached 'H NMR spectrum of the product that you are making today. What...
5. Examine the attached 'H NMR spectrum of the product that you are making today. What significant difference(s) are present (with respect to the spectrum of the dibromide product)? 6. For today's experiment, we are doing a reaction with trans-cinnamic acid using NBS (which effectively provides a dilute solution of bromine) in a mixture of water and methanol. Predict the four possible products of this reaction. Note the dibromide product is not a possibility here. (See question 2). For this...
Questions 1. Given the H NMR spectrum and molec- ular formula for each of the following compounds, deduce the...
Questions 1. Given the H NMR spectrum and molec- ular formula for each of the following compounds, deduce the structure of the compound, estimate the chemical shifts of all its protons using the parameters in Tables 22.3–22.5, and assign the NMR sig- nals to their respective protons. (a) C.H,,Cl; 1H NMR (CDC12): 8 3.33 (2H, s); 1.10 (9H, s) (b) C-H,,0,; 1H NMR (CDC12): 8 3.88 (1H, s); 2.25 (3H, s); 1.40 (6H, s) (C) CH,,0,; 1H NMR (CDC1,): 8...
Considering 1H-NMR analysis of
substituted benzenes (for ortho, para, meta nitrobromobenzene and
ortho, para dinitro bromobenzene, or meta para dinitrobromobenzene)
: What is the splitting patterns for ring hydrogens for the
substituted benzenes? Using ??3-bond and 4-bond J coupling
constants, what are: ??Relative chemical shifts of ring
hydrogens?
15. Indicate those ortho/para director(s) and those meta director(s) - NO2 Br - -C₂Hs - NH2 CoHs nat reagent(s), solvent(s) and chemicals are needed in making a Grignard reagent (C2HsMgBri? Choose from the following list. Water diethyl ether lithium, phenyl bromide, ethyl bromide (MR) iodine, sodium bromide, heat 17. Which one of the following reaction is a nucleophilic aromatic substitution reaction? Which one is an electrophilic aromatic substitution? HNOH,SO 18. Predict the product:
Question1:
Introduction Three aromatic compounds that have ortho-para directing and activating substituents will be brominated. The extent of activation will be judged by the number of bromine atoms that add to the benzene ring in each case. For each of the compounds shown below you will work out if a mono- di- or tri- brominated derivative formed following treatment with acetic acid and bromine in hydrobromic acid. This will be determined by measuring the melting point and interpreting the H...
2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals expected in both the reactant and the product. 2) Provide the carbocation intermediate that allowed the transformation to happen at that position. 3) This molecule is (ortho, meta, para) substituted (circle one). 4) Using resonance arrows show how that carbocation can be distributed (delocalized) to multiple locations on the arene ring system. 5) Predict a different structure that can form from this delocalization. FeBrg,...
2. D type and strength of each substituents as activating(A) or outcome as ortho-para (O/P) or meta(M) directors. (6 pts) you expect an electrophile to be attached to the ring You must identify the deactivating(D) and also the expected regiochemical 3. Use aromatic, non aromatic or antiaromatic concepts to explain the reactions or molecules shown (6 pts) Provide a curved arrow mechanism to show the formation of a aromatic carbocation intermediate Show the final product H-I The pK,values for the...
1. Consider the three molecules below to answer the following questions. Circle TRUE or FALSE at the end of each question (0.5 points each). Molecule A Molecule C Molecule B A. The rate of EAS with Molecule B will be faster than the rate of EAS with Molecule A (assume MAJOR product formation). TRUE or FALSE B. Molecule C will undergo nitration to yield a meta-product that is the MAJOR product. TRUE or FALSE c. The rate of meta-product formation...
Examine H NMR
4. Examine the attached 'H NMR spectrum of the product from the trans-cinnamic acid + Br (dibromide product) reaction in the lab manual. Indicate which part(s) of the dibromide product give rise to the peaks at 5 and 5.5 ppm. OS SOIT -1093.75 SEZO- ES OEDI- H Ả Br 0 " H OH Bri dibromide product 1H NMR (Note the OH is not shown) 6 84 8.2 8.0 7.8 7.6 74 7.2 70 69 6.6 6.4 6.2...
5. Examine the attached 'H NMR spectrum of the product that you are making today. What significant difference(s) are present (with respect to the spectrum of the dibromide product)? 6. For today's experiment, we are doing a reaction with trans-cinnamic acid using NBS (which effectively provides a dilute solution of bromine) in a mixture of water and methanol. Predict the four possible products of this reaction. Note the dibromide product is not a possibility here. (See question 2). For this...
Questions 1. Given the H NMR spectrum and molec- ular formula for each of the following compounds, deduce the structure of the compound, estimate the chemical shifts of all its protons using the parameters in Tables 22.3–22.5, and assign the NMR sig- nals to their respective protons. (a) C.H,,Cl; 1H NMR (CDC12): 8 3.33 (2H, s); 1.10 (9H, s) (b) C-H,,0,; 1H NMR (CDC12): 8 3.88 (1H, s); 2.25 (3H, s); 1.40 (6H, s) (C) CH,,0,; 1H NMR (CDC1,): 8...
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