CHE 2231 Worksheet 7 Substitution and Elimination

Dr. Deborah Bromfield Lee

Instructions: Here you will review the information on choosing between characteristics related to substitution,
the using the Halo triggers, check your answers. Then move on to Elimination. AR Problems – you need your
AR Halo app
Here are the concepts you need to consider in this order for substitution.

Task: Conduct an SN2 reaction

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CHE 2231 Worksheet 7 Substitution and Elimination

#3: Since the LG = Cl for each substrate, then move to #4

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CHE 2231 Worksheet 7 Substitution and Elimination

AR Trigger is the image with the tower and words above. Note other solvents can be used.

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CHE 2231 Worksheet 7 Substitution and Elimination

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CHE 2231 Worksheet 7 Substitution and Elimination

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CHE 2231 Worksheet 7 Substitution and Elimination

#3: Since the LG = I for each substrate, then move to #4

Scan the Halo Trigger next, the solvent may be different but in the same category.

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CHE 2231 Worksheet 7 Substitution and Elimination

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CHE 2231 Worksheet 7 Substitution and Elimination

Scan the Halo Trigger above after trying to which reaction happens to check your answer.

Review Elimination mechanisms: E1 vs E2

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CHE 2231 Worksheet 7 Substitution and Elimination
Nucleophiles vs. Bases

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CHE 2231 Worksheet 7 Substitution and Elimination

SN2

Stereochemistry Overview: Rearrangement and Zaitsev vs Hofmann

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CHE 2231 Worksheet 7 Substitution and Elimination

Notes:

Rearrangement in E1?

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CHE 2231 Worksheet 7 Substitution and Elimination

Z
E
Z

Di neither Tri tetra most stable

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CHE 2231 Worksheet 7 Substitution and Elimination

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CHE 2231 Worksheet 7 Substitution and Elimination

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CHE 2231 Worksheet 7 Substitution and Elimination

Substitution vs Elimination
See Synopsis handout on Canvas and lecture notes along with text.

Review Nu

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CHE 2231 Worksheet 7 Substitution and Elimination

Triage of Substitution

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CHE 2231 Worksheet 7 Substitution and Elimination
Practice problem

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