Organic chemistry tutorials

Exercise 1 O O
Glyphosate, one of the compounds in the herbicide Roundup, has been the
subject of controversy for its "allegedly hazardous activity to health." H
P N
The planar representation of glyphosate can be presented as follows: HO OH
Instruction: OH
1- Give the molecular formula of glyphosate.
2 - Among the different names proposed below, identify the letter or letters (A, B, C) that correspond to the
systematic name (IUPAC) of glyphosate.
A: 2-[(phosphonomethyl)amino]acetic acid
B: glyphosic acid
C: N-(phosphonomethyl)glycine
3 - Give the number of asymmetric carbon with this molecule

Exercise 2
In organic chemistry, with the chemical elements and by various chemical reactions, one can
synthesize the molecule (A) opposite:
O (A)
1- Give the different chemical functions present in
OH
this molecule (A) O
HN
2- Give the number of stereoisomer corresponding
Cl OH
to this molecule

O O
3- Using the rules of nomenclature according to N
IUPAC, name the molecule (A)

Exercise 3 : Tick directly on the test and by a cross, the true or false answer. In case of doubt, refrain from
doing so because a false answer cancels a correct one.

Let us consider the benzyl carbocations A, B, C :

O
CH2 CH2
CH2
H 3C
O H
O
H 3C A B C
TRUE FALSE
a) In general, carbocations are stabilized by attractors.
b) C is the least stable due to the attractive effect of the carbonyl
c) C is more stable than an unsubstituted benzyl carbocation (C 6H 5CH 2+)
d) A and B have almost the same stability
e) The oxygen of the methoxy groups is hybridized sp 3

Exercise 4
We consider the following transformations:

And the following compounds:

Which of the following statements are correct?
a) Transformation 1 leads to compound D.
b) Transformation 1 leads to compound A.
c) Transformation 1 leads to compound C.
d) Transformation 2 leads to compounds E and F.
e) Transformation 2 leads to compound B.

Exercise 5
During a reaction, a molecule (B) can be obtained following the hydrogenation of an aromatic
compound (D). The perspective representation of the molecule (B) and the topological formula of
(D) are as follows:

OCH3 OCH3
(1)

(2)
(B) (D)
COOH COOH

1- Give the geometric isomerism exhibited by this molecule (B) and specify the configuration
descriptors of carbons (1) and (2).
2- Draw the molecule (B) in its most stable conformation.
3- Appreciate the basicity of the molecule (D) with respect to benzoic acid and justify by its
resonance hybrid.

Exercise 6:
In stereochemistry, the Fischer representation of a molecule (C ) can be represented as follows:
COOH

HO H
H3C NC

C2H5 ( C)

1- Write the topological formula of (C) while indicating on it the hybridization state of the oxygen O
and nitrogen N atoms.
2- Propose a Newman projection representation in the shifted form of the C molecule.

Exercise 7

1- Name, according to the systematic nomenclature, the following organic compound:

(a) 6-dimethyl-2,7-dimethylnona-2,5-diene.

b) 6-methylethyl-2,7-dimethylnona-2,5-diene.

c) 6-isopropyl-2,7-dimethylnona-2,5-diene.
2- Let be the following molecule:

Give the absolute configuration of carbons 2 and 3 :

a) Carbon 2 has the absolute configuration R.

b) Carbon 2 has the absolute configuration S.

c) Carbon 3 has the absolute configuration R.

d) Carbon 3 has the absolute configuration S.

e) The double bond is of absolute configuration Z.

f) The double bond is of absolute configuration E.

3- Which of the following carbocations is the most stable by mesomeric donor effect:

A) B) C)

a) Carbocation A is the most stable,

b) Carbocation B is the most stable

c) The carbocation C is the most stable