UIPR-ARECIBO Química Orgánica II

Examen I (2021)

Nombre: ______________________________________ Valor 117.8 puntos

Parte I. Selección múltiple. Escoja la alternativa correcta (utilice la hoja de zipgrade)

(43 x 1.1 = 47.3 puntos)
1. Which of the following compounds is (are) secondary alcohols?

A) Only I B) Only II C) Only II and III D) Only III and IV

2. Which of the following compounds are epoxides?

puede ser III y IV

A) Only I and III B) Only III and IV C) Only I, III and IV D) I, II, III and IV

3. Which of the following compounds is (are) symmetrical ethers?

A) Only I B) Only IV C) Only III and IV D) Only I, III and IV

4. What is the IUPAC of the following compound?

(CH3CH2)3COH
A) 2-Ethyl-2-pentanol C) 3-Ethyl-3-pentanol
B) 2-Ethyl-3-pentanol D) 2,2-Diethyl-1-butanol

5. What is the IUPAC of the following compound?

A) 3,3,6-Trimethylcyclohexanol C) 1,4,4-Trimethyl-2-cyclohexanol
B) 2,5,5-Trimethylcyclohexanol D) 1,1,4-Trimethyl-2-cyclohexanol

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 6. What is the IUPAC of the following compound?

A) 5-Hydroxy-3-methyl-1-pentene C) 3-Methyl-1-penten-5-ol
B) 3-Methyl-5-penten-1-ol D) 3-Methyl-4-penten-1-ol

7. What is the IUPAC of the following compound?

A) (S)-2,2-Dimethyl-3-pentanol C) (R)-4,4-Dimethyl-3-pentanol
B) (R)-2,2-Dimethyl-3-pentanol D) (S)-1-tert-Butyl-1-propanol

8. What is the IUPAC of the following compound?

A) Ethoxyoctane
B) 5-Ethoxyoctane
C) 4-Ethoxyoctane
D) Ethyl octyl ether

9. What is the common name of the following compound?

A) Methyl sec-butyl ether C) sec-Butyl methyl ether

B) Isobutyl methyl ether D) Butyl methyl ether

10. What is the IUPAC of the following compound?

A) 1,2-Epoxy-4-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane
B) 3,4-Epoxy-1-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane

11. What is the IUPAC of the following compound?

A) 1,1-Dimethyloxirane C) 2-Methylpropylene oxide

B) 2-Methylpropylane D) 2,2-Dimethyloxirane

12. Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV

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13. Rank the following compounds in order of increasing boiling point, putting the
compound with the lowest boiling point first.

A) III < II < I < IV C) IV < I < II < III

B) II < III < I < IV D) I < II < III < IV

14. Which of the following reactions will provide the best yield of ether by the
Williamson ether synthesis?
A) Sodium methoxide and tert-butyl bromide.
B) Sodium tert-butoxide and iodomethane.
C) Methanol and tert-butyl alcohol in the presence of KOH.
D) Iodomethane and tert-butyl bromide in the presence of KOH.

15. What is the best choice of reagent to accomplish the following transformation?

A) HCl B) SOCl2, pyridine C) Cl2 D) H3O+, H2O

16. What is the product of the following reaction?

A) I B) II C) III D) IV

17. What is the major organic product(s) obtained in the following reaction?

A) I B) II C) III D) I and II

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18. What is the best choice of reagent to accomplish the following transformation?

A) HCl B) H2SO4 C) NaOH D) TsCl, pyridine

19. Which of the following alcohols reacts the fastest with HCl to give the
corresponding alkyl halide?

A) I B) II C) III D) IV

20. What is the major organic product obtained from the following sequence of
reactions?

A) 2-Methyl-1-butene C) 1-Chloro-2-methylbutane
B) 3-Methyl-3-butene D) 1-Bromo-2-methylbutane

21. Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only II and III

22. Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only I and II

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23. Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4,
putting the least reactive first.

A) I < III < II B) I < II < III C) II < III < I D) III < II < I

24. Which of the following alcohols is most likely to yield a carbocation that is
susceptible to rearrangements?

A) I B) II C) III D) IV

25. What is the best choice of reagent to accomplish the following transformation?

A) TsCl, pyridine B) POCl3, pyridine C) HCl, ZnCl2 D) NaOH

26. What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

27. What is the major organic product obtained from the following reaction?

A) (±)-2-Chlorobutane C) (S)-3-Chlorobutane
B) (R)-2-Chlorobutane D) trans-2-Butene

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28. What is the major organic product obtained from the following sequence of
reactions?

A) (R)-2-Methylpentanenitrile C) (±)-2-Methylpentanenitrile
B) (S)-2-Methylpentanenitrile D) trans-2-Butene

29. What is the major organic product obtained from the following sequence of
reactions?

A) (S)-2-Methoxypentane C) (±)-2-Methoxypentane
B) (R)-2-Methoxypentane D) trans-2-Butene

30. What are the major products obtained upon treatment of ethyl methyl ether with
excess HBr?
A) Bromomethane and ethanol C) Bromoethane and bromomethane
B) Bromoethane and methanol D) Ethanol and methanol

31. Which of the following statements about the reaction of ethers with strong acids
is true?
A) HCl, HBr and HI can all be used.
B) The mechanism of ether cleavage is SN1 only.
C) The mechanism of ether cleavage is SN2 only.
D) The mechanism of ether cleavage is SN1 and SN2.

32. Determine the product in the following reaction (ignoring possible

stereoisomers).

A) I B) II C) III D) IV

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 33. Determine the product in the following reaction (ignoring possible
stereoisomers).

A) I B) II C) III D) IV

34. What is the product of the following reaction?

A) I B) II C) III D) IV

According to the following structures answer question 35, 36 and 37

I II III IV

35. What is the IUPAC name of the compound I?

A. 3-methylbutane-1-thiol
B. 2-methylbutane-1-thiol
C. 3-methylbutane-1-thiol
D. 3-methylbutane-1-thiol

36. What is the IUPAC name of the compound II?

A. isopropyl ethyl sulfide
B. sec-butyl ethyl sulfide
C. sec-propyl ethyl sulfonium
D. isopropyl ethyl disulfide

37. The structure III corresponds to a:

A. thiol B. disulfide C. sulfonium D. sulfide

38. The structure IV corresponds to a:

A. thiol B. disulfide C. sulfonium D. sulfide

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39. 2-Metil-1-butanol se clasifica como un __________.
A. alcohol primario
B. alcohol secundario
C. alcohol terciario
D. un fenol

40. El nombre IUPAC para el siguiente compuesto es:

A. cis-1-cloro-3-ciclohexanol
B. trans-1-cloro-3-ciclohexanol
C. cis-3-clorociclohexanol
D. trans-3-clorociclohexanol

41. ¿Cuál de los siguientes es el carbocatión más estable?

A) D)

B) E)

C)

42. El siguiente éter de corona se clasifica como:

A) 18-crown-6
B) 12-crown-4
C) 6-crow-4
D) 8-crown-4
E) Ninguna de las anteriores

43. El orden en incremento en solubilidad en agua de los siguientes compuestos es:

A B C

A) A>B>C
B) A>C>B
C) B>A>C
D) C>A>B
E) B>C>A

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Parte II. Complete las siguientes reacciones según corresponda.
A. Reacciones de alcoholes (19.5 puntos)
Escriba el producto formado cuando el 1-butanol (CH3CH2CH2CH2OH) es tratado con los
siguientes reactivos (ah)

a. H2SO4  _______________________

b. NaH _______________________

c. SOCl2, piridina _______________________

d. HBr _______________________

e. TsCl, pridina _______________________

f. producto (b) con CH3CH2Br _______________________

g. producto (e) con NaOCH2CH3 _______________________

h. producto (e) con NaCN _______________________

i. y j.
OH

TsOH

______________ + ____________
k.

_______________________

l.

__________________

m.

__________________
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B. Reacciones de éteres (7.5 puntos)

a. y b.

_____________ + ______________

c.

___________________
d. y e.

__________________ + _____________
d. Haluro de alquilo e. Alcoxido

C. Reacciones de tioles, sulfuros, disulfuros (7.5 puntos)

a.

____________________

b. y c.

_________________ + ________________

d.

___________________

e.

___________________

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D. Reacciones de epóxidos

Escriba el producto formado (en la tabla) cuando el epóxido mostrado es tratado con los siguientes
reactivos: (9 puntos)
O

a. b. c.

d. e. f.

III. Mecanismos

Escriba el mecanismo paso por paso de la siguiente reacción. Indique con flechas el movimiento de
los electrones, las especies intermediarias y haga una breve descripción del paso según
discutido en la clase.

1. Deshidratación de alcoholes. (ojo ocurre re-arreglo) 6 puntos

CH3 CH3

CH3 H2SO4

OH
CH3
Mecanismo 1.

2. Reacción de alcoholes 3° con HX vía SN1 (4 puntos)

C H3 OH C H3 Br
HBr
+ H2 O

Mecanismo 2
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IV. Síntesis. Proponga la forma de efectuar las siguientes conversiones sintéticas.

Síntesis 1 (4 puntos)
?

Síntesis 2. (4 puntos) OH CN
?

V. Complete la siguiente tabla con los reactivos que permitan llevar las transformaciones
según indica el diagrama (9 puntos)

a. b. N/A c.

d. e. f. N/A

g. h.

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