When 2-bromo-3-methylbutane reacts with ethanol,two products are formed, 2-ethoxy-3-methylbutane and 2-ethoxy-2-methylbutane. 1.Give an explanation for the...
When 2-bromo-3-methylbutane reacts with ethanol,two products are formed, 2-ethoxy-3-methylbutane and 2-ethoxy-2-methylbutane.
1.Give an explanation for the two products.
2. Draw the full mechanism for the formation of the second product. (mechanism should have fours steps in total, including a deprotonation step.)
Please show all work!
Homework Answers
1) The reaction of ethanol with 2-bromo-3-methylbutane proceeds via SN1 mechanism which involves the formation of a carbocation intermediate. In this case one product is formed from the carbocation arising directly out of C-Br bond dissociation.
However, the original carbocation can also rearrange via 1,2- hydride shift to give a more stable carbocation. This rearranged more stable carbocation gives rise to the second product.
2)
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When 2-bromo-3-methylbutane reacts with ethanol,two products are
formed, 2-ethoxy-3-methylbutane and 2-ethoxy-2-methylbutane.
1.Give an explanation for the...
2-Bromo-2-methylbutane undergoes an E1 elimination reaction in the presence of ethanol. In the next reaction only one o...
2-Bromo-2-methylbutane undergoes an E1 elimination reaction in
the presence of ethanol. In the next reaction only one of the
possible products is represented. Although the product shown is not
the major product of the reaction, notice that there is more than
one way it can be produced. Complete the mechanism and draw the
missing substances.
Draw all missing reactants and/or products in the appropriate
boxes by placing atoms on the grid and connecting them with bonds,
including charges where needed....
Organobromine compounds are used in fire retardants, fumigants, and biocides. 2-bromo-3-methylbutane reacts with Substitution Product Elimination...
Organobromine compounds are used in fire retardants, fumigants, and biocides. 2-bromo-3-methylbutane reacts with Substitution Product Elimination Product Br a. Identify the alkyl bromide as 1°, 2°, or 3° b. Identify the nucleophile as strong or weak and big or small. c. Draw the structures of the substitution and elimination products. Use curved arrows to show how the elimination products form. d. Which product is major product? Give reasons. e. If C2HsOH is used instead of C2HsO, will the same major...
1. 3-methyl-1-butene on reaction with H-Cl forms two products, namely 2-chloro-3- methylbutane (minor) and 2-chloro-2-methylbutane (major)....
1. 3-methyl-1-butene on reaction with H-Cl forms two products, namely 2-chloro-3- methylbutane (minor) and 2-chloro-2-methylbutane (major). Illustrate the mechanism for the formation of these two products. Use curved arrows to illustrate electron movement and all intermediates must be shown. 2. 3,3-dimethyl-1-butene on reaction with HBr forms two products, namely 3-bromo-2,2- dimethylbutane (minor) and 2-bromo-2,3-dimethylbutane (major). Illustrate the mechanism for the formation of these two products. Use curved arrows to illustrate electron movement and all intermediates must be shown. 3. Calculate...
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the...
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the presence of heat forms Br. H30* and two organic products. Draw a stepwise mechanism for this reaction, clearly showing how each product is formed. Use curved arrows to show electron movement, and include all reactive intermediates, resonance structures, etc. Br H20
1.1What is the major product formed upon radical bromination of (S)-3-methylhexane? Select the best response. Draw...
1.1What is the major product formed upon radical bromination of (S)-3-methylhexane? Select the best response. Draw the full mechanism. A. (S)-3-bromo-3-methylhexane B. (R)-3-bromo-3-methylhexane C. A mixture of (R) and (S) 3-Bromo-3-methylhexane D. (3R)-1-bromo-3-methylhexane 1.2 What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?Select the best response. Draw the mechanism. A. 2,3-dibromo-2-methylbutane B. 2-bromo-3-methylbutane C. 2-bromo-2-methylbutane D. (E)-1-bromo-2-methyl-2-butene 1.3 There are 4 major products formed upon treatment of (E)-3-methyl-2-hexene with HBr...
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the...
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the presence of heat forms Br", H3O+ and two organic products. Draw a stepwise mechanism for this reaction, clearly showing how each product is formed. Use curved arrows to show electron movement, and include all reactive intermediates, resonance structures, etc. Br H2O Δ
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On standing, 2-bromo-3-methylbutane is converted into 2-bromo-2-methytbutane. Propose a curved-arrow mechanism for this transformation. The reaction...
On standing, 2-bromo-3-methylbutane is converted into 2-bromo-2-methytbutane. Propose a curved-arrow mechanism for this transformation. The reaction of butylamine, CH_3(CH_2)NH_2, with 1-bromoethane in 60% aqueous ethanol follows the rate law Rate = k[butylamine][1-bromobutane] The product of the reaction is (CH_3CH_2CH_2CH_2)_2NH_2-Br^-. The following very similar reaction, however, has a first order rate law: Give a mechanism for each reaction that is consistent with its rate law and with other facts about nucleophilic substitution reactions. Use the curved-arrow formalism.
(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two...
(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two cycloalkenes, and which would you expect to be the major product? Write conformational structures showing how each is formed. (b) When trans-1-bromo-2-methylcyclohexane reacts in an E2 reaction, only one cyclo- alkene is formed. What is this product? Write conformational structures showing why it is the only product.
2-Bromo-2-methylbutane undergoes an E1 elimination reaction in
the presence of ethanol. In the next reaction only one of the
possible products is represented. Although the product shown is not
the major product of the reaction, notice that there is more than
one way it can be produced. Complete the mechanism and draw the
missing substances.
Draw all missing reactants and/or products in the appropriate
boxes by placing atoms on the grid and connecting them with bonds,
including charges where needed....
Organobromine compounds are used in fire retardants, fumigants, and biocides. 2-bromo-3-methylbutane reacts with Substitution Product Elimination Product Br a. Identify the alkyl bromide as 1°, 2°, or 3° b. Identify the nucleophile as strong or weak and big or small. c. Draw the structures of the substitution and elimination products. Use curved arrows to show how the elimination products form. d. Which product is major product? Give reasons. e. If C2HsOH is used instead of C2HsO, will the same major...
1. 3-methyl-1-butene on reaction with H-Cl forms two products, namely 2-chloro-3- methylbutane (minor) and 2-chloro-2-methylbutane (major). Illustrate the mechanism for the formation of these two products. Use curved arrows to illustrate electron movement and all intermediates must be shown. 2. 3,3-dimethyl-1-butene on reaction with HBr forms two products, namely 3-bromo-2,2- dimethylbutane (minor) and 2-bromo-2,3-dimethylbutane (major). Illustrate the mechanism for the formation of these two products. Use curved arrows to illustrate electron movement and all intermediates must be shown. 3. Calculate...
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the presence of heat forms Br. H30* and two organic products. Draw a stepwise mechanism for this reaction, clearly showing how each product is formed. Use curved arrows to show electron movement, and include all reactive intermediates, resonance structures, etc. Br H20
Gradescope #2 This question is worth 10 points. The reaction between (R)-2-bromo-3-methylbutane and water in the presence of heat forms Br", H3O+ and two organic products. Draw a stepwise mechanism for this reaction, clearly showing how each product is formed. Use curved arrows to show electron movement, and include all reactive intermediates, resonance structures, etc. Br H2O Δ
6) 5-Hydroxypentanal reacting with ethanol under acidic catalysis forms two enantiomers and o Show full mechanism of products formation. (6 points) i Label each step of the reaction as protonation, nucleophilic addition with cyclization, elimination, nucleophilic addition, or deprotonation. (2 points) (ii) Circle the oxonium ion intermediate. (I points) i) Make one sentence statement why racemic mixture will be the product of the reaction. (I points)
6) 5-Hydroxypentanal reacting with ethanol under acidic catalysis forms two enantiomers and o Show...
On standing, 2-bromo-3-methylbutane is converted into 2-bromo-2-methytbutane. Propose a curved-arrow mechanism for this transformation. The reaction of butylamine, CH_3(CH_2)NH_2, with 1-bromoethane in 60% aqueous ethanol follows the rate law Rate = k[butylamine][1-bromobutane] The product of the reaction is (CH_3CH_2CH_2CH_2)_2NH_2-Br^-. The following very similar reaction, however, has a first order rate law: Give a mechanism for each reaction that is consistent with its rate law and with other facts about nucleophilic substitution reactions. Use the curved-arrow formalism.
(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two cycloalkenes, and which would you expect to be the major product? Write conformational structures showing how each is formed. (b) When trans-1-bromo-2-methylcyclohexane reacts in an E2 reaction, only one cyclo- alkene is formed. What is this product? Write conformational structures showing why it is the only product.
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