For each reaction shown below 1. Identify the nucleophile and the electrophile. 2. Predict the product(s) of the reaction. 3. Decide whether the reaction is more likely to proceed via an SN2 or SN1 reaction mechanism. 4. If one of the products is chiral, try to predict whether it will be (S), (R), or a mixture of both. ho H₂C "H CH₂ OH HO Br

For each reaction shown below 1. Identify the nucleophile and the electrophile. 2. Predict the product(s) of the reaction. 3. Decide whether the reaction is more likely to proceed via an SN2 or SN1 reaction mechanism. 4. If one of the products is chiral, try to predict whether it will be (S), (R), or a mixture of both. ho H₂C "H CH₂ OH HO Br

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles

Section: Chapter Questions

Problem 2Q

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1. Which of the following is the strongest nucleophile? Refer to the diagram below with an MeOH, MeSH, etc. 2. Which of the following is true about the stereochemistry of SN1 reaction?a.retention of configuration at the electrophilic centerb.50:50 mixture of retention and inversion of configuration at the electrophilic centerc.inversion of configuration at the electrophilic centerd. slightly more inversion than retention at the electrophilic center
Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methyl butane (a moderately hindered 2∘ alkyl halide) with sodium ethoxide. Do not worry about stereochemistry in the SN2 product for this problem. Don't forget about stereochemistry.
Consider the following reaction being performed with a low concentration. Think about what type of substitution mechanism will be favored, SN2 or SN1, and what product will result.
The SN1 reaction is a two-step reaction, and the first step of this reaction is the formation of a carbocation intermediate. Draw the carbocation intermediates that form from the alkyl chlorides in tubes 8 and 15. 2. Again, use tubes 8 and 15 to answer the following question. In general, the more stable carbocation forms faster. Given this, which carbocation is more stable, or do they have the same stability?
Draw the molecule: Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other.Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2∘∘ alkyl halide) with sodium ethoxide. Do not worry about sterechemistry inther SN2 product for this problem. Don't forget about stereochemistry.
Assume that 2-chloropropane reacts with CN− in an SN2 reaction. Use the JSME editor () to draw the structure of the substitution product of the reaction. The guide on how to draw your structure can be found here Important Note: When drawing the structures in the JME editor please adhere to the following formats: 1. If the nucleophile is OH−, DO NOT manually add the "H" to the final product 2. If the nucleophile is CN−, be sure to include the appropriate bonding between the C and N in the final product
Fill in the information based on the type of reaction mentioned in each column. A. Draw the line angle diagram of a substrate that will undergo SN1, SN2, E1, E2 B. Draw the line angle diagram of a nucleophile that can be used for SN1, SN2, E1, and E2 C. Draw the line angle diagram of a solvent that can be used with SN1, SN2, E1, and E2 D. Write down if the stereochemistry of the product will be inversion, retention, or a 50:50 ratio of inversion and retention
Is NaOCH2CH3 also a strong nucleophile? if so and Br wasn't a 3 degree alkyl halide, would it also undergo an Sn2 reaction? what would the major product be then?
In the box to the left of each reaction below, write the mechanism by which it occurs (could be SN1, SN2, or E1, or even 2 of them). Then draw the product(s).
A carbocation intermediate is central to which of these reaction types? E1, E2, SN1, SN2 ? Choose 1
For each of the following reactions diagram the steps from the substrate to the product. For each step, a) over the reaction arrow supply the needed reagents b) name the type of reaction/mechanism {ROS (SN1, SN2, radical) E(E1, E2) A [acid-base, addition (carbocation, onium bridge, radical)]}
Why we need step 3 before step 4? a. Because the nitro group increases the electrophilicity at the ortho positions which is where the bromine is added. b. Because the amine group is a strong ortho, para director which is what controls the regiochemical outcome of this bromination. c. Step 4 is unessesary. The symmetry of compound 3 allows for the bromination to be regioselective and give compound 5. 5. There will be a mixture of products because there is no selectivity for a major product.