UNIVERSIDAD DE CHILE FACULTAD DE CIENCIAS DEPTO.

DE QUMICA
DOCENCIA 2011
QUIMICA ORGANICA II 1ER SEMESTRE
Dr. Orlando Muoz
GUIA DE EJERCICIOS 1
Alcoholes Fenoles Esteres Epxidos - Tiocompuestos
1.- Seale la estructura de los siguientes compuestos:
a)
b)
c)
d)
e)
f)
g)
h)

8-cloro-5-(1-cloro-3-hidroxipropil)-1,7-octanodiol
3-(-4-clorobutil)-1,4-pentanodiol
3-isoproxi-1-butanol
cis-1-etil-3-fenoxiciclohexano
4-clorofenol
2-naftol
2-ciclohexentiol
4-etil-tio-2-metil-2-penteno

2.- Seale el nombre para las siguientes estructuras:

CH2 - CH = CH2

S CH3

a)

b) C2H5O (CH2)3 Cl

c)

d)

O
Cl

O CH3

OH

3.- Provide the structure of the major organic product in the reaction below.

Answer:
4.- Provide the reagents necessary to carry out the transformation shown below.

5.- 2-Methylpentan-3-ol is classified as __________.

A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol
6.- Provide an acceptable name for the compound below.

Answer:
7.- Provide the reagents necessary to accomplish the following transformation.
2-methyl-2-octene to 2-methyloctan-3-ol
8.- Provide the structure of the major organic product in the reaction shown below.

Answer:

9.- Provide a detailed, stepwise mechanism for the reaction of acetyl chloride (CH3COCl) and 2 equivalents
of PhMgCl.
Answer:

10.- Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?
A) BrCH2CH2CH2CN
B) CH3COCH2CH2Br
C) (CH3)2NCH2CH2Br
D) H2NCH2CH2Br

E) all of the above

11.- When a ketone is treated with LiAlH4 followed by addition of H2O, what general class of product
results?
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) ether
E) aldehyde
12.- Provide the IUPAC name for the compound below.

13.- Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?
A)

B)

C)

D)

E) both A and D
Answer:

14.- Provide a detailed step-by-step mechanism that would account for the formation of the product in the
following reaction.

Answer:
15.- Provide the structure of the major organic product in the reaction below.

Answer:
16.- Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In the oxidation
of propran-1-ol, provide the structure of this ester and give the mechanism for its conversion to the
intermediate aldehyde.
Answer:

Diff: 2
17.- Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its
formation.
(CH3)3CCH2OH + HBr
18.- Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol)
to 4,4-dimethylpentan-2-ol?
A) 1. HCl
2. Mg
3. CH3CHO
4. H3O+
B) 1. HCl, ZnCl2
2. Mg
3. CH2O
4. H3O+
C) 1. SOCl2
2. Mg
3. CH3CHO
4. H3O+
D) 1. HCl, ZnCl2
2. Mg
3. CH3CHO
4. H3O+
Answer:
19.-Provide a detailed, stepwise mechanism for the reaction below.

20.- What series of synthetic steps could be used to carry out the transformation shown below?

21.-Provide the major organic product of the following reaction.

Answer:
Diff: 2

22.- Predict the outcome of the following sequence of reactions.

23.-Provide a structural representation of 1,2-epoxybutane (also called 2-ethyloxirane).

Answer:

24.- Provide the major organic product in the reaction below.

CH3CH2CH2OH

1. Na

2. PhCH2Br

Answer:
25.- Suggest a reasonable mechanism for the reaction shown below.

Answer:

26.- Provide the major organic product in the reaction below.

Answer:
27.- Provide the major organic product in the reaction below.

Answer:
28.- Which of the following is produced by the reaction of (CH3CH2)2S with CH3CH2I?
A) CH3CH2CH2CH2I
B) (CH3CH2)3S+ IC) (CH3CH2)3S
D) CH3SCH2CH2CH3
E) CH3CH2SCH2CH2I
Answer: