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Chem12A Winter 2014 Chad Miller Foothill College

Concept Problems for Wade Chapter 6 1. Draw the structure of the product that accounts for 27% of the product distribution and the two structures that account for the racemic mixture below.

2.

Draw the transition state structure for the SN2 reaction below.

3.

What nucleophile can be introduced into the reaction in order to accelerate the very slow hydrolysis of the alkylchloride below? H2O + RCH2Cl RCH2OH + HCl

4.

Explain if the leaving group, L, below can participate in an SN2 substitution reaction.

5.

Chem12A Winter 2014 Chad Miller Foothill College


6. Draw the intermediates for the reaction below.
+

(CH3)3CCH2I + CH3CO2 Ag

(CH3)2(CH3CH2)COCOCH3

7.

Draw the substitution products for the following three reactions. Note that the nucleophiles are ambident nucleophiles which can potentially react with either of two heteroatoms. NaNO2 + BrCH2COOR AgNO2 + BrCH2COOR Na2SO3 + BrCH2COOR

8.

Draw the products of the following solvolysis (reaction with methanol as solvent).

9.

Draw the product of the following reaction indicating stereochemical outcome and identify the type of mechanism.

10. Draw the product(s) of the reaction below, indicating stereochemistry and identify the type of mechanism.

Chem12A Winter 2014 Chad Miller Foothill College

11. Draw the product of the reaction below, indicating stereochemistry and identify the type of mechanism.

12. Consider the problem below.

13. Consider the treatment of Molecule X with the strong base, potassium t-butoxide, in butanol.

14. Consider the activation of hydroxyl to transform it into a better leaving group by Lewis acids H and BF3. Draw the products for the second reaction.

Chem12A Winter 2014 Chad Miller Foothill College

15. Reactions can be accelerated if there are neighboring groups that can participate in internal substitution reactions that also render stereochemical outcomes. This neighboring group participation or anchimeric assistance occurs when such groups do participate in the reaction.

16. Consider the neighboring group participation reactions below. Propose a mechanism that explains the stereochemical outcome.

17. Draw the mechanisms of the following reactions that involve neighboring group participation.

18. Consider the compound below. OTs represents a tosyl group which is a very good leaving group. What potential structure would the intermediate ? have below?

Chem12A Winter 2014 Chad Miller Foothill College


19. Consider the following substitution reactions of the bromocyclohexane compounds below.

20. Consider the following reaction of tert-amyl bromide.

Chem12A Winter 2014 Chad Miller Foothill College


21. Consider the reaction of styrene below. Draw compounds A, B, X and Y.

22. Consider the following molecule A. Indicate the mechanism using curved arrow formalism.

Chem12A Winter 2014 Chad Miller Foothill College


23. This is not a problem but it is a solution for your reference.

24. Consider the following intramolecular substitution reactions. Draw each product below and identify the type of substitution reaction.

Chem12A Winter 2014 Chad Miller Foothill College


Additional material for Wade Chapter 6 The following tables are found in J.B. Hendrickson, D.J. Cram and G.S. Hammond, Organic Chemistry, McGrawHill, New York, 1970, pp. 401-405