2º CURSO DEL GRADO EN QUÍMICA - ASIGNATURA: QUÍMICA ORGÁNICA I

EJERCICIOS TEMA 5

1. Rank the following molecules according to their reactivity in an SN2 reaction.

e) Concerning the stereochemistry of the reactions performed with KCN as nucleophile.

What are the expected products?

f) Write the nomenclature of the expected products from section “e”.

2. Rank the following molecules according to their reactivity in an SN1 reaction.

c) If ethanolysis reactions are performed, what is the expected stereochemical result for those
reactions?

3. Propose a one-step synthetic method for the preparation of the following products:

a) Benzoato de (S)-but-2-ilo

b) (1R,3S)-1-Isopropil-3-yodociclohexano

c) Draw the mechanism and the energy profile in each case.

4. Explain which of the following couples of reactions is expected to proceed faster. (DMSO
stands for Dimethylsulfoxide, and DMF stands for Dimethylformamide)

a)

b)

c)

d)

5. What are the expected products in the following reaction:

a) Draw the mechanism leading to the expected major product.

b) Draw the energy profile corresponding to the previous mechanism.
c) Do you expect any difference in the evolution of the reaction if (1R,2R)-2-
methylcyclohexanol is used as starting material.

6. Complete the following reaction schemes and draw the arrows to explain each of the
mechanisms

a)
b)

c)

d)

e)

f)

g)

7. Explain the mechanism which leads to the products of the following reactions. Do you expect
to obtain a major product in each case?

a)

b)
8. Complete the following reaction schemes and draw the arrows to explain each of the
mechanisms.

a)

b)

c)

9. Would the given product be the only expected product in each case?

10. What is the major product expected in the following reactions?

11. Which stereoisomer of 2-bromociclohexanol can produce 7-oxabicyclo[4.1.0]heptane when
reacting with a strong base?
Justify your answer and draw the reaction mechanism using sodium hydride as strong base.

12. a) Compound A reacts 200 times faster than B in an E2 reaction. Why?

b) Draw the expected products for the E2 reaction from A and B.

A B

13. Complete the following reaction schemes and draw the corresponding mechanisms.

a)

b)

c)

14. Would you expect differences in the major products of the following reactions?

a)

b)
c)

15. Propose a synthetic route to obtain tert-butyl benzoate (benzoato de terc-butilo) using
2-methylpropane (2-metilpropano) as starting material.

16. Propose two alternative synthetic methods for the preparation of tert-butylmethyl
ether (terc-butilmetileter)

17. Explain how 2,4-dimethylpent-1-ene (2,5-dimetilpent-1-eno) can be obtained from

2,4-dimethylpentan-3-ol (2,4-dimetilpentan-3-ol)