Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids3h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

7. Substitution Reactions

SN2 Reaction

Organic Chemistry

7. Substitution Reactions

SN2 Reaction

Multiple Choice

Choose the S_N2 reaction that will occur the fastest.

The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 3-carbon alkane chain is depicted as a line structure using 2 zigzag lines. C 2 is single bonded to C H 3 on the lower left in the form of a line and single bonded to C l on the lower right.
The second reactant has the following structure: A 2-carbon alkane chain is depicted as a line structure using 1 line. C 2 is single bonded to O superscript minus on the lower right. D M S O is written under the reaction arrow.

The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant is C H 3 I. The second reactant has the following structure: A 3-carbon alkane chain is depicted as a line structure using 2 zigzag lines. C 2 is single bonded to C H 3 on the lower left in the form of a line and single bonded to O H on the lower right.

8:33m

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Related Practice

Textbook Question

Will the following Sₙ2 reaction proceed more rapidly in DMSO or H₂O?

<IMAGE>

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Textbook Question

Write the rate law for the following reaction and identify which molecules are present in the rate-determining step. Draw a possible transition state and propose a mechanism.

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Textbook Question

Predict the major products of the following substitutions. e. 1-chloropentane + NaI —>

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Textbook Question

Predict the major products of the following substitutions. d. CH3CH2CH2I + NaCN —>

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Textbook Question

Predict the major products of the following substitutions. b. HC≡C:- Na+ sodium acetylide + 1-chlorobutane CH3CH2CH2CH2Cl —>

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Textbook Question

For each pair of compounds, state which compound is the better SN2 substrate. a. 2-methyl-1-iodopropane or tera-butyl iodide. b. cyclohexyl bromide or 1-bromo-1-methylcyclohexane

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Textbook Question

Predict the products of the following SN2 reactions. e.

+ CH3I —> f. (CH3)3C—CH2CH2Br + excess NH3 —>

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Textbook Question

Predict the products of the following SN2 reactions. a. CH3CH2ONa + CH3CH2Cl —> b.

Predict the compound in each pair that will undergo the SN2 reaction faster. (a)

Draw the substitution product formed by each of the following SN2 reactions: a. trans-1-iodo-4-ethylcyclohexane and methoxide ion b. cis-1-chloro-3-methylcyclobutane and ethoxide ion

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Textbook Question

Draw the products obtained from the SN2 reaction of: c. (S)-3-chlorohexane and hydroxide ion. d. 3-iodopentane and hydroxide ion.

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Textbook Question

Which alkyl halide is more reactive in an SN2 reaction with a given nucleophile? c.

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Textbook Question

Rank the following alkyl bromides from most reactive to least reactive in an SN2 reaction: 1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.

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Textbook Question

Which alkyl halide is more reactive in an SN2 reaction with a given nucleophile? a.

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Textbook Question

Does increasing the energy barrier for an SN2 reaction increase or decrease the magnitude of the rate constant for the reaction?

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Textbook Question

a.Which reaction had the larger rate constant?

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Textbook Question

Draw a transition state for the following substitution reaction. H₃C―C ≡ C⁻ Na⁺ + H₃C―Cl → H₃C―C ≡ C―CH₃

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Textbook Question

Predict the major products of the following reactions. (a) ethyl tosylate + potassium tert-butoxide (b) isobutyl tosylate + NaI (c) (R)-2-hexyl tosylate + NaCN

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Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions. (a)

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Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions. (b)

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Textbook Question

Which Sₙ2 reaction would you expect to be faster? Explain your answer. vs.

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Textbook Question

(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction. (b) vs.

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Textbook Question

(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction. (d) vs.

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Textbook Question

The following reaction, though run under standard solvolysis conditions, occurs via an Sₙ2 reaction. Why?

<IMAGE>

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Textbook Question

(•••) Crown ethers are able to solvate cations based on their size. Specifically, 15-crown-5 forms stable complexes with sodium. How would the addition of a crown ether change the rate of an Sₙ2 reaction?

<IMAGE>

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Textbook Question

Cardura, a drug used to treat hypertension, is synthesized as shown here. + K2CO3—> A KOH—> B HCl, H2O—> Cardura + CH3OH b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?

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Textbook Question

Propose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product:

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Textbook Question

The S_N2 reaction is the concerted, backside displacement of a good leaving group by a nucleophile [see Chapter 12]. Why do nucleophiles attack from the back in S_N2 reactions?

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Textbook Question

(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction.

(a) <IMAGE> vs. <IMAGE>

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Textbook Question

(••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'

(f) <IMAGE>

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Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions.

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Textbook Question

(•) For each pair, choose the nucleophile that would react most quickly in an Sₙ2 reaction (assume H₂O is the solvent).

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Textbook Question

(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction.

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Textbook Question

In which solvent—ethanol or diethyl ether—would the equilibrium for the following SN2 reaction lie farther to the right?

<IMAGE>

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Textbook Question

How will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent?

b. <IMAGE>

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Textbook Question

How will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent?

c. CH3CH2I+NH3→CH3CH2N+H3 I−

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Textbook Question

Show all the products, including their configurations, that are obtained from the above reaction.

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Textbook Question

You were told in [SECTION 7.11] that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.

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Textbook Question

Would you expect acetate ion (CH₃CO₂⁻) to be a better nucleophile in an S_N2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?

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Textbook Question

Draw a perspective structure or a Fischer projection for the products of the following SN2 reactions.

e. <IMAGE> + NaOCH3 CH3OH—>

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Textbook Question

Draw a perspective structure or a Fischer projection for the products of the following SN2 reactions.

f. <IMAGE> + NH3 excess

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Textbook Question

Predict the compound in each pair that will undergo the SN2 reaction faster.

(d) <IMAGE> or <IMAGE>

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Textbook Question

For each pair of compounds, state which compound is the better SN2 substrate.

c. 2-bromobutane or isopropyl bromide

d. 1-chloro-2,2-dimethylbutane or 2-chlorobutane

e. 1-iodobutane or 2-iodopropane

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Textbook Question

Triethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4-, is a solid with melting point 91–92 °C.

Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction.

What is the leaving group?

Why might this reagent be preferred to using an ethyl halide?

(Consult [TABLE 6-2] <IMAGE>)

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Textbook Question

b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with azide ion

(-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)

<IMAGE>

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Textbook Question

Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3).

b. Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH3+ Br−), which is deprotonated by the excess ammonia to give the amine.

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Textbook Question

Draw a perspective structure or a Fischer projection for the products of the following SN₂ reactions.

a. trans-1-bromo-3-methylcyclopentane + KOH

b. (R)-2-bromopentane + KCN

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Textbook Question

Draw a perspective structure or a Fischer projection for the products of the following SN2 reactions.

c. <IMAGE> + NaI acetone—>

d. <IMAGE> + NaSH

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Textbook Question

Predict the major products of the following reactions.

(d) the tosylate of cyclohexylmethanol + excess NH₃

(e) n-butyl tosylate + sodium acetylide, <IMAGE>

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Textbook Question

Rank the following compounds in decreasing order of their reactivity toward the SN2 reaction with sodium ethoxide (Na⁺ ^-OCH2CH3) in ethanol.

Methyl chloride

Tert-butyl iodide

Neopentyl bromide

Isopropyl bromide

Methyl iodide

Ethyl chloride

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Textbook Question

When (±)−2,3−dibromobutane reacts with potassium hydroxide, some of the products are (2S,3R)-3-bromobutan-2-ol and its enantiomer and trans-2-bromobut-2-ene.

Why is no cis-2-bromobut-2-ene formed?

3 bromobutan-2-ol <IMAGE> <IMAGE>

trans-2-bromobut-2-ene <IMAGE>

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Textbook Question

a. Which reacts faster in an SN2 reaction?

<IMAGE>

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Textbook Question

a. Explain why the alkyl halide shown here reacts much more rapidly with guanine than does a primary alkyl halide (such as pentyl chloride).