Organic Chemistry SN1/SN2/E1/E2 Problems
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Questions and Answers

Match the following reactions with their expected outcome:

Br + NaN3 = NR H3C Br + NaOH = OH, Br Br + NaOH (excess) = OH, Br Br + CH3ONa (heat) = Anti elimination product

Match the compounds with their corresponding nucleophiles/electrophiles for synthesis:

OH = Water (H2O) CH3 = Methyl iodide (CH3I) NH2 = Amine chloride (RNH3+) O = Epoxide

Match the nucleophile with its relative reactivity:

OH = Better nucleophile than H2O SH = Better nucleophile than H2S NH2 = Better nucleophile than OH (CH3CH2)3P = Better nucleophile than (CH3CH2)3N

Match the compounds with the faster reacting pathway:

<p>Br (better LG) = SN2 pathway Less hindered Br = Faster SN2 reaction 2° Cl = SN1 pathway Resonance stabilized Br = Faster SN1 reaction</p> Signup and view all the answers

Match the described reactions with their specific conditions:

<p>CH2Br + CH3OH (heat) = Form CH2 + CH3 H3C Br + KOCH(CH3)3 (heat) = Major elimination product Br + NaOH = Produces OH, Br Br + NaN3 = No reaction (NR)</p> Signup and view all the answers

Match each reaction with its appropriate outcome:

<p>(a) Br + NaN3 = NR (b) OH + NaBr = Pyr, OH, 2O-5-CH3 (c) OH + H3C-S-CI = Br, Br, NaBr (d) Br + NaOH, NaBr (excess) = OH, no SN2 at sp2 carbon</p> Signup and view all the answers

Match the nucleophile/electrophile pairs for synthesizing the indicated compounds:

<p>(a) OH = NaOH + CH3Br (b) CH3 = CH3Br + NaOCH3 (c) NH2 = NH3 + CH3Br (d) O = H2O + CH3Cl</p> Signup and view all the answers

Match the nucleophile with the likely reaction type that would occur:

<p>(a) Br = SN2 (b) CH3 = Elimination (c) SH = Substitution (d) OH = NR</p> Signup and view all the answers

Match the better nucleophile in each pair:

<p>(a) OH vs H2O = OH (b) SH vs H2S = SH (c) NH2 vs OH = NH2 (d) I vs Br = I</p> Signup and view all the answers

Match the compound that will react faster in the given condition:

<p>(a) Br vs Cl (SN2) = Br (b) 2° Br vs 2° Cl (SN1) = Cl (c) Br vs Cl (better LG, SN1) = Cl (d) Br vs Br (less hindered, SN2) = Br</p> Signup and view all the answers

Study Notes

SN1/SN2/E1/E2 Practice Problems

  • Draw the structure of the major organic product for each reaction.
  • Do not forget stereochemistry.
  • If there is no reaction, write NR.

Problem (a)

  • Br + NaN3 + CH3CN
  • No reaction given

Problem (b)

  • Aromatic ring + NaBr + OH + Pyr
  • No reaction given

Problem (c)

  • Aromatic ring + H3C-S-Cl + OH
  • No reaction given

Problem (d)

  • Br + NaOH (excess) + acetone
  • No SN2 at sp2 carbon.
  • Products not given.

Problem (e)

  • H3C Br + NaOH
  • Assume SN2
  • Products not given

Problem (f)

  • Aromatic ring + Na + Br
  • Elimination reaction
  • Products not given

Problem (g)

  • Aromatic ring + CH3 CH3ONa
  • Products not given

Problem (h)

  • Br + CH2CH3
  • Assume Elimination
  • Products not given

Problem (i)

  • CH3 CH2CH3 + CH3CH2Br + NaOCH3 + acetone
  • Products not given

Problem 2

  • Show the nucleophile/electrophile pairs to synthesize compounds.

Problem 3

  • Detailed reaction mechanism for given reactions.

Problem 4

  • Circle the better nucleophile in each pair.

Problem 5

  • Circle the compound that reacts faster in an indicated pathway.

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SN1/SN2 Practice Problems PDF

Description

Test your understanding of SN1, SN2, E1, and E2 reactions with these practice problems. This quiz challenges you to predict major organic products, including considerations of stereochemistry and reaction mechanisms. Analyze various nucleophile/electrophile pairs and demonstrate your grasp of organic synthesis.

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