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NOTES BOOK(Organic Chem)

NOTES BOOK(Organic Chem)

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Published by: farah_mspy on Apr 22, 2010
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12/02/2012

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Chapter 1REVIEW1.1 BONDSWhat is the difference between ionic and covalent bonds? Ininorganic chemistry we learnedabout ionic and covalent bonds. In ionic bonding, electrons are lost by one element, a metal,and electrons are gained by the other element, a nonmetal. The strongest bond is the ionicbond. It is formed by an attraction of oppositely charged ions (electrostatic attraction).Covalent bonding involves a sharing of electrons between two elements. In organic chemistry,bonding is usually covalent and specifically the C-C and C-H bonds are nonpolar covalentbonds. Covalent bonds are classified as polar or nonpolar depending on the difference of Pauling's electronegativity values (see chart in front of text) of the two bonded atoms. If thedifference in electronegativities is less than 0.5, the bond is mainlynonpolar covalentand if thedifference ranges between 0.5 and 1.6 the bond is mainlypolar covalent. Differences inelectronegativities greater than 1.6 usually means the bond is mainlyionic. To calculate theen (change in electronegativity values) for a C-H bond we look below:
atom electronegativity value (env)*C2.5H2.1en(change in env) = 0.4
*Pauling's electronegativity values are found opposite the front cover.Therefore C-H is a nonpolar covalent bond.1.2 HYDROGEN BONDSAnother type of bond, although weak, is very important in determing physical properties of organic molecules. This bond is known as ahydrogen bond. For hydrogen bonding to occur aH on one molecule must be bonded to either an oxygen (O) or a nitrogen (N) or a fluorine (F) of an another molecule, as seen below:
CH
2
CH
2
CH
2
CH
3
OH The net effect of hydrogen bonding is to associate molecules making themolecule appear to have a larger molecular weight.)(
hydrogen bond
:CH
3
CH
2
CH
2
CH
2
OH
11
 
Remember the H on one molecule hydrogen bonds to a O (in this case) of another molecule.In the examples below circle the molecules which would exhibit hydrogen bonding in the liquidstate:a. HF b. CH
3
OH c . CH
3
OCH
3
d. H
2
Oe. CHBr
3
When H is bonded to one of these atoms there is a marked increase in boiling and meltingpoints and increased water solubility. We can see the effect on hydrogen bonding by looking atthe boiling points of the following molecules in table 1.1. Note the molecular weight of thesemolecules are essentially the same. All things being equal, i.e, no H- bonding,the usual effect of increasing molecular weight is to increase the boiling point (bp), but in the examples below wesee an unusually high bp in the first molecule relative to the other two.Why?_____________________________________________________TABLE 1.1
 35°C 36°Cbp: 118°CMW: 74 g/mol 74 g/mol 72 g/molCH
3
CH
2
CH
2
CH
2
CH
3
CH
3
CH
2
CH
2
CH
2
OHCH
3
CH
2
OCH
2
CH
3
1.3 VALENCEValence is the number of bonds aNEUTRALatom can form. Table 1-1 shows the valencesthat make up what is known as the valence rules for a few of the more common elements. Thevalence rules correspond to the number of electrons required to complete the elementsoutershell.Table 1-1VALENCE RULES TO BE MEMORIZEDATOM #BOND(S)H1F,Cl,Br,I1O2N3C4Knowing the valence rules will allow you to draw molecules; for example, CH
4
O. In becominga molecular architect, you must follow some simple rules:a)place the atom that can form the greatest number of bonds in themiddle of the molecule
22
 
b) obey the valence rulesLet's see what we can now do with CH
4
O.Of the atoms in this molecule, the atom that can form the greatest number of bonds is - C.Surround the C as symmetrically as possible with the other atoms in the molecule. Obeying thevalence rules we obtain:
 
HCOHHH
Using the valence rules, draw structural formulas for: CO
2
, CI
4
, CH
5
N.CO
2
CI
4
CH
5
N1.4 LEWIS DOT FORMULAIn drawing a correct Lewis Dot formula use only the outershell (valence) electrons for eachatom. Sharing a pair of electrons indicates a single bond; sharing two pair of electronsindicates a double bond; and sharing three pairs of electrons indicates a triple bond.RULES:a) Separate the molecule or ion into atoms. Place the atom that can form thegreatest number of bonds in the center of a polyatomic moleculeb) Write correct Lewis Dot formula for each atomc) Without adding or subtracting electrons, share the available electrons sothat a stable molecule results, i.e., a full outershell of electrons should beattained by all atoms.**The full outershell of electrons should occur when the shared electrons are countedtwice- once for each atom sharing those electrons.Take a closer look at these rules in writing the correct Lewis Dot Formula (LDF) for CBr
4
.
33

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