4. Why does the reaction of trans-1-bromo-2-methylcyclohexane yield the non-Zaitsev elimination product 3-methylcyclohexene on treatment with...
Organic Worksheet How can you explain that trams-1-bromo-2-methylcyclohexane yields the non-Zaitsev elimination product 3-methylcylcohexene on treatment with base? 1-chloro-1,2-diphenylethane can undergo E2 elimination to give either cis or trans- 1,2,diphenylethylene. Draw Newman projections of the reactive conformations leading to both possible products, and suggest a reason why the trans alkene is the major product.
11/8/19 The cis- and trans-isomers of 1-bromo-2-methylcyclohexane are shown below. One of these isomers undergoes E2 elimination 50 time faster than the other. Illustrate the E2 mechanism using the chair conformers to explain why one isomer is much faster and give the major product of each reaction. 1-BUOK 1-BOK Illustrate the Sw2 mechanism for the reaction below and show what has happened to the stereochemistry of the compound. NaCN acetone
2. When (1R, 2R)-1-bromo-2-methylcyclohexane reacts with lithium methoxide in methanol, both substitution and elimination reactions occur to produce three unique products. What are the structures of the three products produced by this reaction? sepenbare CHOLE сно CH3 3. When (R)-3-mesyl-3-ethyloctane reacts with potassium hydroxide in aqueous THF elimination occurs to produce three unique alkene products. What are the structures of the three products produced by this reaction? MsOCH.CH HOK THF/H20 4. When (S)-2-fluoro-2-iodobutane reacts with hydroxide ion in aqueous THF,...
(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.
Why are the halide ions the only nucleophiles that work well in acidic conditions? trans-1-bromo-2-methylcyclohexane reacts with KOH via the E2 mechanism to form an alkene. Draw the structure of the product.
Draw the most stable conformation for; a. trans-1-chloro-3-methylcyclohexane b. cis-1-ethyl-2-isopropylcyclohexane c. trans-1-bromo-4-ethylcyclohexane d. cis-2-bromo-1-methylcycclohexane Sppecifically, show the ring flipping and calculate the strain using the table given in the power point slides.
* Your answer is incorrect. Try again. Predict the product for the following reaction. NaSH cis-1-bromo-3-methylcyclohexane acetone нас SH HC a н НС Br Hz WISH HU "SH W OOOO
4. When 1-iodo-1-methylcyclohexane is treated with sodium ethoxide, the more highly substituted alkene product predominates. Alternatively, when potassium tert-butoxide is used as a base, the less substitute alkene predominates. Give the structures of the two bases, and the two products and explain the difference in regioselectivity. 5. Draw the diastereomer of the compound shown below. Explain which chair conformation one will react faster in the presence of a strong base to give a substituted cyclohexene. (Draw the chair structure of...
4. The reaction between cis-1-bromo-2-methylcyclohexane and ethoxide (a very strong base) results in an E2 reaction. (refer to Mechanism 9.8 in your textbook) a. Show the transition state for this reaction. CHE + CH, CH, CH, OH b. Show the formation of the product(s) from the transition state. c. Use the rule from part 3d, to determine the major and minor alkene products.
Elimination Reactions Prelab Date 1. Explain why we get a different product when we use bulky bases compared to smal bases. (3 pts) 2. If we start with 25.0 mL of 0.100 M sodium methoxide and 25.0 g of 2-bromobutane, what will be the theoretical yield of your product? (Use dimensional analysis/ Do not break up your steps/Read the beginning of your lab to guide you on how to do this problem). (3 pts) 3. How can one determine which...