Video Solution: Predict the major organic product of each of the following r...

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Organic Chemistry / E2 - Cumulative Practice / Problem #18101

Predict the major organic product of each of the following reactions. In spite of the structural complexity of some of the starting materials, the functional group transformations are all of the type described in this chapter. 

 

Draw the predominant product expected for each of the following E2 reactions.

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The reaction between compound 1 and NaOCHMe2 in Me2CHOH as a solvent produces a mixture of two different products 2 and 3, containing a double bond, with a relative yield of 50% and 50% respectively. What are the structures of compounds 2 and 3?

b.  Which one of products 2 or 3 will be obtained as the major product if we do this reaction with MeO- +Na as the base in MeOH as solvent? Explain your answer with 1-2 sentences

c. Which one of products 2 or 3 will be obtained as the major product if we do this reaction with (CH3)3CO- +Na as the base in (CH3)3COH as solvent? Explain your answer with 1-2 sentences

d. Based on the data above, what products and in what relative ratios would we obtain by treating compound 4 with NaOCHMe2 in Me2CHOH as the solvent under the same conditions as above? Explain your answer with 1-2 sentences.

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For the reaction shown below, draw the structure of the major product(s). Where appropriate, write "No Reaction". Assume all chiral starting materials are optically pure. Show stereochemistry where appropriate. Indicate whether the product exists as a single enantiomer or a racemic mixture.

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Draw a Newman projection with the antiperiplanar conformation through C1(front)‐C2(rear) bond to predict the product shown below.

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When (3R, 4S)-4-bromo-3-methylheptane is treated with strong base, such as potassium tert-butoxide in tert-butanol at 100 °C an elimination reaction takes place and produces one major product and two minor products.

A. Draw the correct structure for the starting material.

 

 

B. Draw the structure of the thermodynamically-favored major product.

 

 

C. Draw the structures of two kinetically-favored minor products.

 

 

D. The formation of the thermodynamic product occurs through a stereoselective mechanism. In 1-2 sentences explain why this mechanism is stereoselective.

 

 

E. One of the minor products is formed in higher yield than the other minor product. In 1-2 sentences explain why this minor product is formed in higher yield in terms of the relative thermodynamic stability of the two products. You must adequately account for the different factors that affect stability.

 

 

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Propose a mechanism for the following reaction.

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Consider the reactions shown and answer the associated questions. 

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 Provide the major product for the following reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Provide the full mechanism and draw the final product for the following E2 reaction. 

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Predict the product(s) for the following reaction.

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Predict the product(s) for the following reaction.

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Which compound will be the organic product after the following two steps:

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Fill in the missing intermediate, reagent, and product for this synthesis.

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Which of the following statements applies to the E2 mechanism?

a) It proceeds through the more stable carbocation intermediate.

b) It occurs with racemization of stereochemistry.

c) The C-H and C-X bonds that break must be anti.

d) It occurs with inversion of stereochemistry.

e) Use of a bulky base gives the more highly substituted alkene product.

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Draw the structure of the major product in box 1. Complete the chair conformation of 1-bromo-2,4-dimethylcyclohexane in box 2 showing all hydrogens.

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Draw the product of the E2 elimination of (1S,2R)-1,2-dibromo-1,2-diphenylethane (shown below left). Draw the product in the box below provided and complete the Newman projection of (1S,2R)-1,2-dibromo-1,2-diphenylethane looking along C1 to C2 in the correct geometry required to yield the product.

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Compare the following reactions and decide which reaction in each pair would occur faster. Write your answer and concisely defend your choice. No reasoning, no points.

 

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One of the stereoisomers below undergoes E2 reactions in the presence of a stong base MUCH faster than the other. (Selecting the correct isomer is not enough to earn points on this question! Your explanation should be sufficiently clear and complete that the reader/grader is left with no doubt that you understand.)

  1. Construct both the chair and its flipped conformer for the two stereoisomers below
  2. Determine which stereoisomer will have the faster rate of reaction:           a)         or         b)
  3. Explain this observation mechanistically using full sentences making sure to answer the question of WHY one will undergo an E2 reaction faster than the other.
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