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

EJERCICIOS TEMAS 1 Y 2

1.- Draw the line bond structure (representación de enlaces) of the following compounds
and determine the hybridization of each carbon atom. Recall the bond angles to draw the
correct molecular geometry.

a) 2-phenylacetaldehyde (2-fenilacetaldehído)
b) 2-methoxyacetonitrile (2-metoxiacetonitrilo)
c) 3-oxopropanamide or 2-formylacetamide (3-oxopropanamida o 2-formilacetamida)
d) allylethynylamine (aliletinilamina)
d) cyclopent-2-enone (ciclopent-2-enona o 2-ciclopentenona)
e) 3-phenylpropiolonitrile (3-fenilpropiolonitrile)
f) 3-oxobutanoic acid or acetylacetic acid (ácido 3-oxobutanoico o ácido acetilacético)
g) 2-vinylcyclobutanone (2-vinilciclobutanona)

2.- Write structural formulas which correspond to these molecular formulas. Determine
the hybridization of each atom.
a) C3H8 b) C3H6 c) C3H4

3.-Draw five constitutional isomers (isómeros estructurales) with the molecular formula
C5H8O which fulfill the following requirements:

a) A molecule which has a ketone functional group.

b) A molecule which has an aldehyde functional group.
c) A molecule which has an ether functional group.
d) A molecule which has a heterocyclic structure.
e) A molecule which has a cyclic hydrocarbon structure

4.- Draw the line bond structures of the following compounds, showing all non-bonding
electrons. Identify the carbon atoms as primary, secondary, tertiary or quaternary.

a) 2,2,4-trimethylpentane (2,2,4-trimetilpentano)
b) isopropyl tert-butyl ether (isopropil terc-butiléter)
c) 2-amino-2,3,4-trimethylcyclopentan-1-ol (2-amino-2,3,4-trimetilciclopentan-1-ol)
d) 2-bromo-3-nitrobutan-1-amine (2-bromo-3-nitrobutan-1-amina)

5.- Draw molecular structures which meet the following features:

a) An alkane with a quaternary carbon atom and a secondary carbon atom.
b) A secondary alcohol which also has a tertiary carbon atom.
c) A tertiary amine which also has two secondary carbon atoms.
d) A secondary amide which also has three primary carbon atoms
6.-Draw the non-bonding electrons and/or the formal charge to the following molecules.

a) b) c) d) e)

f) g) h) i) j)

7.- Specify which atoms, if any, bear formal charge in the following compounds.

8.- Which of the following molecules would you expect to be polar? Indicate where the positive
and negative electron densities are more localized and draw the arrow representing the
approximate orientation of the dipole moment.

a) 1,2-dichlorobenzene (1,2-diclorobenceno)
b) diethylamine (dietilamina)
c) 3-hydroxypropanone (3-hidroxipropanona)
d) dichloromethane (diclorometano)
e) but-2-ene (but-2-eno)

9.- According to their expected reactivity identify the following compounds as nucleophiles,
electrophiles, Lewis acid, Lewis base, Bronsted acid or Bronsted base. Some of the compounds
could show more than one type of reactivity. Highlight which atom constitutes the reactive centre
in each case. Explain your answer.

OEt O
Br
O Na OH H2N OH
a) O b) c) d) ZnCl2 e) OH f) g) NaH

O O O O
Ph Ph
P
O O Na Cl N
h) i) j) Ph k) K2CO3 l) m)
10.- Define the following reactions according to their mechanisms. Identify the reacting species
as nucleophile, electrophile, acid, base, oxidising agent or reducing agent.

THF O O
+ NaH THF
+ 2 H2 + 2 NaBr + CH3I + Et3N + Et3NH+I-
a) Br Br b) OH O

OH O
PCC,
Et2O
DMF EtO-Na+, EtOH
+ KI + KCl + NaI + EtOH
c) Cl I d)

O OH
H 2O Cl
+ HCN h
CN + Cl2 + HCl
e) f)

CO2Et LiAlH4, H2O

Et2O OH + HBr

g) h) Br

Br
MeO-Na+, MeOH O
OH Pd-C, MeOH + NaBr + MeOH
OH
+ 2 H2
i) j) OH

11.- In the following reaction profile:

a) Place all the reacting species from reactants to products.

b) Which is the rate determining step?
c) Is the reaction intermediate resulting from the rate determining step more prone to go forward
to the product or to revert to the reactants?
d) How would you favour the evolution of the reaction towards the formation of the products?

12.- Draw a reaction energy diagram where

a) the product is thermodynamically unstable and kinetically unstable.

b) the product is thermodynamically unstable and kinetically stable.
13.- Are the following carbocations correctly ranked according to their stability? Would you
expect any gain in stability from some of these carbocations?

H H H
H3C CH3
C > H3C C C > H3C
C
CH3
CH3 CH3 H

14.- Which of the following structures have delocalised electrons?

O

O C CH3
H3C N

a) b) H2C CHCH2CH CH2 c) d) CO32- e) f) CH3

15.- Draw contributing resonant structures for the following compounds. Do they all contribute
equally to the structure of the hybrid?

a) b) c) d) e)

f) g) h) i)

j)

16.- Which intermediate is more stable in the following pairs? Explain your answer.

or
O
or O or
a) b) c)

17.- Is the following structure correct? Draw contributing resonant structures.

O
N
O

18.- Which of the following alcohols is more acidic? Explain your answer.

OH
OH or
19.- Which of the following amines is more basic? Explain your answer.

, ,

20.- Which of the bold-typed protons is more acidic? Explain your answer.

a) CH3CO2H, FCH2CO2H, BrCH2CO2H

H H H
O
b) , ,

21.- Rank the following groups of species according to: 1st) Their Bronsted basicity; 2nd) Their
nucleophilicity.

a) H2O, HO-, CH3CO2-

b) Br-, I-, F-, Cl-
c) H2O, H2S, NH3
d) F-, HO-, CH3S-
e) MeS-, PhS-, (CH3)3CS-

22.-Tell whether the following reactions are an oxidation, a reduction or another type of reaction.

a) b)

c) d)

e)

f) g)

23.- What are the expected species to be obtained in the following reactions?

a) b)

c) d)
e) f)

g) h)

i)

24. Classify the framed groups as good, average or bad leaving groups.

a) b) c) d) e) f)

g)