Purification by sublimation

A solid substance is transformed directly into gaseous form without passing through the liquid phase
during sublimation process.

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The figure above show the energy requirement and transformations involving the most common
substance water. Similar phase diagram is expected to other substances including solid.

Sublimation is applied in the purification of naphthalein balls.

Materials: naphthalein balls, soup bowl, colored paper, paste, pan, stove, wet tissue paper.

Procedure;
1. Ground the naphthalein balls.
2. Paste a colored paper into the inner bottom of a soup bowl. If the inner portion of the soup
bowl is colored, the paper lining to be pasted is NOT required.
3. Place the powdered naphthalein into the pan.
4. Cover the napthalein in the pan with an inverted soup bowl.
5. Place the wet tissue paper over the inverted soup bowl.
6. With the stove, Use low fire in heating the pan for 5 minutes.
7. Turn off the stove, and let the set up cool for 5 minutes.
8. Remove the inverted soup bowl , take a picture of what is formed in the paper lining of the
soup bowl.

Safety Precaution:
1.Use face mask.
2. Care must be observed as heat is involved in the activity.
3. Be sure to wash thoroughly all the kitchen wares used in the activity.
Evidence of output.
Pictures of the set-up, close up picture of the bottom of the soup bowl, and selfie with what is formed
in the paper lining/or bottom of the soup bowl.

RESONANCE
Resonance was developed to resolve the structure when the Lewis structure may be more than one
structure.

Resonance Basic Principles

1.Resonance occurs when a compound cannot be represented by a single Lewis structure.

2.Two resonance structures differ only in the position of non-bonded electrons and Pi bond.

3.The resonance hybrid is the only accurate representations for a resonance stabilized compound.

A hybrid is more stable than any single resonance structure because electron density is delocalized.

JUMPING ELECTRONS, MOVING ELECTRONS

Double-head arrow represent resonance between Lewis structure. ENCIRCLE

One curved-headed arrow show the movement of each electron. The tail begins at an electron pair( a
bond or lone pair) while the head points to where the electron pair moves.

Delocalization start with the atom with lone pair and the delocalization extend over several nuclei.

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(Let the students show/draw the arrows and flash their output for checking)

1.H2C+ - CH = CH- CH3 ↔ H2C=CH -C+ H-CH3 Pi electron delocalization towards the bond of the
positive carbon.

2. Carbonate, CO3==>

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Two oxygen singly bonded to Carbon have three lone pairs, and are negatively charged

lone pair- pi electron delocalization starts at the lone pair of the third oxygen below carbon atom

The third oxygen will be doubly bonded to the carbon and the other two oxygen will be negatively
charged and have three lone pairs.
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Resonance structure of disubstituted benzene

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Resonance structures of fused rings.

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Difference between resonance structures

*two isomers differ in the arrangement of both atoms and electron
*resonance structures differ only in the arrangement of electrons

Charge in Resonance structures

The net charge is the same in both structures.

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SA-NC
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COMPUTATION OF FORMAL CHARGE

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Formal charge= number of valence electron- the number of electron an atom OWNS

Formal charge = number of valence electron-[number of unshared electron + ½ the number of shared
electrons]

Use the formulas in the three species of Carbon:

For sp3 C Carbon share 8 electrons FC= 4-[0 +1/2(8)]= FC= 4- 4=0

For sp3 Carbocation - C+ Carbon share 6 electrons FC = 4-3 =+1

For sp3 Carbanion -C:- Carbon share 6 electrons  FC = 4-[2+1/2(6)] = -1

A charge on a C atom takes the place of 1 H atom. A negatively charged C has one lone pair, and a
positively charged C has none.
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1.Compute the formal charge of each atom in the structures of CO2 above

A. First structure (Linear)

For the two oxygen  FC oxygen= 6- [4 + ½(4)] = 0
For the carbon FC carbon = 4- [0+1/2(8)] = 0
B. Second structure
Triply bonded oxygen FC = 6-[2+1/2(6)]= +1
Carbon FC = 4-[0+1/2(8)]=0
For the second oxygen FC = 6-[ 6+1/2(2)]= -1
C. For the third structure
First oxygen FC = 6-[4+1/2(4)] =0
Second oxygen  FC = 6-[0+1/2(8) ]= +2
Carbon  FC= 4-[4+1/2(4)]= -2

Which of the structures of CO2 is least reactive? Linear structure of CO2

Which is the most stable. Linear structure of CO2.

2. CH3-N≡C :

For the methyl C  FC = 4-[0+1/2(8)]= 0

For the Nitrogen  FC = 5-[0+1/2(8)]= +1

For the second C  FC = 4-[2+1/2(6)]= -1

3. Supply the lone pairs in the incomplete structure of O3 and compute the formal charge of each
oxygen. Hint: the disarrayed order of formal charges are +1, 0 and -1

O=O-O

4. Determine the formal charge of oxygen in H3O

5. Determine the formal charge of nitrogen in NH4

Starting from the middle structure of CO3 draw arrows to the adjacent resonance structures. Compute
the formal charges of each atom in the three structures.

Structural Effect:

The main objective is recognition at site. This term is broad. It include the movement of electron to
enrich a portion of the molecule while depleting other parts; prediction whether a reaction is possible
and the type of a reaction a molecule undergo. The movement of Pi electrons and lone pairs and
distortion of electron density are involved.

1.Delocalization of Pi electrons. This involved sp2 hybridized Carbon which has an unused electron.

CH3-CH2-CH=CH-CH2-CH3 The two unused electrons of the adjacent sp2 carbon are not delocalized.

CH3-CH2-CH=CH-CH=CH2 There are four adjacent sp2 carbons. Their unused four electrons are
delocalized; their movement is simply back and forth.

CH3-CH2-CH=CH-CH2-CH2-CH2-CH2-CH=CH2. Is delocalization possible?

Benzene, C6H6, has 6 sp2 carbons connected alternately with three double bonds and three single
bonds. Sometime a circle is drawn as a replacement of the alternating bonds; the circle represent the
ring current of electrons that are continuously delocalized.
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licensed under CC BY-SA-NC

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2.Lone pair delocalization

Lone pair are none binding. Nitrogen, oxygen, carbon and sulfur have sp2 and one Pi electron. The lone
pair should be associated or near an atom with p orbital.
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3.Sigma electron delocalization also known as CH hyperconjugation.

Hyperconjugation is possible if an sp3 hybrid carbon is right next to a carbon with p orbital. A carbon
with Sp3 has 75 % p character and therefore there is a degree of overlap with the p orbital of its
neighbor to result in sigma electron delocalization or hyperconjugation.
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