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

Flashcards

Nucleophile strength

The ability of an atom or molecule to donate an electron pair to form a chemical bond.

SN1 reaction

A substitution reaction where the rate-determining step involves the loss of a leaving group to form a carbocation intermediate.

SN2 reaction

A substitution reaction where the nucleophile attacks the electrophile from the opposite side of the leaving group (in one step).

Leaving group ability

The ability of a group in a molecule to leave as an anion or neutral molecule during a substitution reaction.

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Elimination reaction

A reaction where a small molecule is lost from a larger molecule to form a double bond.

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SN2 vs E2 with Strong Base

When a strong base is used with a primary or secondary alkyl halide, both SN2 and E2 reactions are possible. The product distribution depends on the structure of the alkyl halide, the strength of the base, and the reaction conditions.

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Leaving Group Ability and SN1/SN2

The leaving group's ability to depart as an anion or neutral molecule influences the rate of SN1 and SN2 reactions. A good leaving group is a weak base, thus readily leaving.

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Better Nucleophile

A nucleophile is an electron-rich species that can attack an electrophile. A better nucleophile is more readily donating an electron pair, forming a new bond.

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SN1 vs SN2 with Tertiary Alkyl Halide

Tertiary alkyl halides favor SN1 reactions because the carbocation intermediate is stabilized by hyperconjugation. SN2 is unlikely due to steric hindrance by the bulky alkyl groups.

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Weak vs Strong Base in SN1

Strong bases favor E2 reactions while weak bases and protic solvents favor SN1 reactions. The choice of base can significantly influence the outcome of a reaction.

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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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Related Documents

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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