4.

Lecture on Organic Chemistry Part 3

OVERVIEW OF ORGANIC COMPOUNDS Factors in determining boiling point

FACTORS BOILING POINT
REVIEW OF PART 2 ↑ Intermolecular forces ↑ Boiling pt
Nomenclature ↑ Length of carbon atoms ↑ Boiling pt
 Alkynes ↑ Branching ↓ Boiling pt
 Aromatic Hydrocarbons Degree of saturation and varies
- Unsaturated Type of bond
- Made up of simply C and H but they contain pi Angle Varies
bond e-
 Alkynes Functional groups
-have 2 pi bonds = triple bond  Unique group of elements or compounds that can
 Aromatic hydrocarbons somewhat define the physical and chemical
-Sp2 properties of organic compounds
-unique feature: very stable configuration
-subjected to SUBSTITUTION REACTION = ALCOHOLS
more stable FUNCTIONAL GROUPS W/ CARBON SINGLY BONDED TO AN
- Very stable ELECTRONEGATIVE ATOM
- SUBSTITUTION REACTION
-Mode of interaction : London dispersion forces
(movement of e-)
– changes with pi bonds and angle
Properties
 Melting point
 Boiling point
 Intermolecular forces of attraction

ALKANES ALKENES ALKYNES

Single bond Double bond Triple bond
109.5 degrees 120 degrees 180 degrees
Sp3 Sp2 Sp
Nonpolar Nonpolar Nonpolar  OXYGEN has high electronegativity (partial negative)
Low e- density High e- density High e- density  In a nonpolar hydrocarbon is added with OH-, it
Higher boiling pt Low boiling pt Highest boiling pt will become polar
 HYDROGEN has low electronegativity (partial
ALKYNES have the highest boiling point positive)
 London dispersion forces are higher in areas w/ high  Alcohols are organic compounds that contain an –OH
e- density group attached to a saturated carbon atom
 State structure :  The general formula for an alcohol is R-OH. Where R
 Stuck altogether is an alkyl group
 Better Vander Waals of Attraction (movement
of e-) Classification of Alcohols
 Good interaction among hydrocarbons w/ triple
bond = high boiling point 1. Methanol
2. Primary alcohol
ALKANES have the second highest boiling point 3. Secondary alcohol
 Single bond saturated that are fixed at an angle 4. Tertiary alcohol
 There may be differences in structure but they are
easy to stuck up/bind altogether = good Vander 2, 3, 4 – depends on the number of alkyl groups attached to
Waals of Attraction the carbon containing the functional group

ALKENES have the low boiling point

 Even though there is a presence of pi bond, the
ANGLE is a different factor = creation of KINKS
 KINKS or LOOPS changes the structure
 Irregular structure = bad Vander Waals of Preparation of Alcohols
Attraction ALCOHOL
 PI BOND is not the basis for determining boiling
point. It is the ANGLE

SUMMARY
 Triple bonds (Alkynes) – loaf bread
 Double bonds (Alkenes) – irregularities (kinks)
 From an unsaturated hydrocarbon (alkene) added
 Single bonds (Alkanes) – structured angles but
with water and sulphuric acid as catalyst = ALCOHOL
different arrangement
 The hydrogen will be binding w/ a carbon atom
 Addition reaction by adding water
 4. Lecture on Organic Chemistry Part 3

ALDEHYDE PHYSICAL PROPERTIES OF ALCOHOLS

 Alcohol molecules hydrogen bond to each other and
to water molecules. They thus have higher than-
normal boiling points, and the lower-molecular-mass
alcohols are soluble in water

 Hydrogenation
 Aldehyde group, carbon bonded with hydrogen
added with water and a catalyst = ALCOHOL

KETONE

CHEMICAL PROPERTIES OF ALCOHOLS

 Intramolecular dehydration of alcohols to give
alkenes

Nomenclature of Alcohols
Rule 1
Name all of the carbon atoms of the molecule as a single alkyl
 Intermolecular dehydration of primary alcohols to
group
give ethers
Rule 2
Add the word alcohol, separating the words with a space
 Oxidation of primary alcohols to give aldehyde and a
carboxylic acid

IUPAC rules for naming alcohols that contain a single hydroxyl

group:
Rule 1  Oxidation of secondary alcohols to give ketone
Name the longest carbon chain to w/c the hydroxyl group is
attached. The chain name is obtained by dripping the final –e
from the alkane name and adding the suffix –ol
Rule 2
Number the chain starting at the end nearest the hydroxyl  Oxidation of tertiary alcohols will not react at all
group, and use the appropriate number to indicate the
position of the –OH group
Rule 3
Name and locate any other substituents present
Rule 4  Production of an alkyl halide from an alcohol by
In alcohols where the –OH group is attached to a carbon substitution using PX3 (X is Cl or Br)
atom in a ring, the hydroxyl group is assumed to be on carbon
Examples

CHEMICAL REACTIONS OF ALCOHOL

Combustio Oxidation Dehydrati Helogenati
n on on
-O2 (air) is -KMnO4 or -H2SO4 -PCl3 or
required K2CrO3 catalyst PBr are
-Heat and are required sources of
light are common -180C halogen
produced oxidizing temp for atoms
agents intramolec -Heat is
ular required
dehydratio
n
140C temp
for
intermolec
ular
dehydratio
n
Alcohol  1alcohol Intramolec Alcohol 
CO2 + H2O  ular : alkyl halide
aldehyde alcohol 
 4. Lecture on Organic Chemistry Part 3

 alkene  The chemical reactions of phenols are significantly

carboxylic Intermolec different from those of alcohols, even though both
acid ular: types of compounds possess hydroxyl groups
1alcohol  Phenols are more resistant to oxidation and do not
2alcohol  ether undergo dehydration
 ketone  Phenols have acidic properties, whereas alcohols do
not
3alcohol  Acidic : donate protons ; metals such as Na ; alkoxide
 no ions
reaction
 Basic : accept proteins ; methanol interacting w/
Health application hydroxyl group ; promotes protonation ; oxonium
Oxidation of ethanol for “breathalyser test” ion (protonated)
 Ethyl alcohol will be oxidized leading to the creation
of products that can be detected by analyzers
 Ethyl  Aldehyde  Carboxylic Acid

Health application
Phenol as Antiseptic
Ethyl and Isopropyl Alcohol as Disinfectants  First antiseptic utilized in surgery
 Ethyl alcohol will be oxidized leading to the creation  Joseph Lister
of products that can be detected by analyzers  Has hydroxyl group and destroys the membranes if
 Can created a bonding with the substituents or harmful microorganisms
microorganism’s membrane  It is a poision/toxic
 If hydroxyl group (OH-) from the alcohol is added,thr
side chain of these microorganisms with bind to it ETHERS
resulting to LYSIS  Structure is the same w/ alcohol group but w/o
 They disrupt the binding or microorganisms to its hydroxyl group
side chains  Bent shape structure
 We use 70% alcohol to penetrate easily  Preparation
 Soluble - Intermolecular dehydration of alcohols
 It is also used in alcohol beverages - Williamson synthesis from alkyl halides and Na
 It metabolizes the liver = affects the metabolism of alkoxides or Na phenoxides (based on
glucose = low blood sugar substitution)
 Interference to cell metabolism
 Deposition of fats in the liver
 Can affect the CNS  Weakly polar
 Not much applications to health
PHENOLS
Nomenclature
 General formula Ar-OH, where Ar represents an aryl
Rule 1
group derived from an aromatic compound
For unsymmetrical ethers, name both hydrocarbon groups
 The parent name is phenol. Ring numbering always
bonded to the oxygen atom in alphabetical order and add the
begins with the hydroxyl group and proceeds in the
word ether, separating the words with a space. Such ether
direction that gives the lower number to the next
names have three separate words w/in the,
carbon atom bearing a substituent. The numerical
position of the hydroxyl group is not specified in the
name because it is 1 by definition
Examples:

Note: Alkoxy group is an –OR group, an alkyl (or aryl) group

attached to an oxygen atom
PROPERTIES OF PHENOLS
 Phenols are generally low-melting solids; most are
only slightly soluble in water
 4. Lecture on Organic Chemistry Part 3

Health application
Thiols and Sulfhydryl Reagents
 Sulfhydryl Reagents are reagents that promotes cell
lysis, specifically of the disulfide bonds through
reduction
Rules for naming an ether using the IUPAC system:  Pentameric- entity composed of 5 units (IgM)
Rule 1  IgM are very large to the point that they hide the
Select the longest carbon chain and use its name as the base presence of IgG antibody
name  In order to find IgG, in the lab, we utilize sulfhydryl
1. Longest chain and use as the base name reagents such as dithiothreitol
2. Change the -yl into -oxy to obtain the alkoxy group name  Dithioltreitol- destructs disulfide bonds of the IgM to
3. Place the alkoxy name, with a location number in front of reveal IgG
the base chain
Thioether (R-S-R)
An organic compound in which a sulfur atom is bonded to
two carbon atoms by single bonds. The generalized formula
for a thioether is R-S-R
Examples:

CYCLIC ETHERS

PROPERTIES OF ETHERS
 Lower boiling point than alcohols because ether
SUMMARY : ALCOHOLS, THIOLS, ETHERS, AND THIOETHERS
molecules do not bond hydrogen molecules with
each other
 walang hydrogen na available; di
makakapag form ng H bonds with each
other, but can form H bonds with water
 Slightly soluble in water because water forms
hydrogen bonds with ether

Health application
Ethers as General Anesthetics
 Promotes pain relief
 Flammable
 Chemists promoted halogenation para di maging
cause ng nausea and vomiting ang anesthesia

PHYSICAL PROPERTIES

Nomenclature Carbonyl Group

 Carbon atom double-bonded to an oxygen atom
 Named in the same way as alcohols in the IUPAC
 Polar in nature
system, except that the -ol becomes -thiol
 thio- indicates the substitution of a sulfur atom for
an oxygen atom in a compound
 Mercaptan is similar to thiol

CHEMICAL PROPERTIES
 Oxidation of a thiol to give a disulphide
 The oxidizing agent will harvest the
hydrogen of the thiol, in order to form
disulfide bond
 Removal of hydrogen

 Reduction of a disulfide to give a thiol

 4. Lecture on Organic Chemistry Part 3

FUNCTIONAL GROUPS W/ CARBON-OXYGEN DOUBLE BOND placing a number immediately before the name of
(CARBONYL GROUPS) the parent chain
4. Determine the identity and location of any
substituents, and append this information to the
from of the parent chain name
5. Cyclic ketones are named by assigning the number 1
to the carbon atom of the carbonyl group. The ring is
then numbered to gove the lowest number(s) to the
atom(s) bearning substituents
Examples:

Aldehyde and Ketone

 Aldehyde- terminal carbonyl carbon atom
 Ketone- inner carbonyl carbon atom

Preparation

Nomenclature of Aldehydes
1. Select as the parent carbon chain the longest chain that
includes the carbon atom of the carbonyl group
2. Name the parent chain by changing the -e ending of the
corresponding alkane name to -al
3. Number the parent chain by assigning the number 1 to the
carbonyl carbon atom of the aldehyde group
4. Determine the identity and location of any substituents,
and append this information to the front of the parent chain
name
Examples:

Properties of Aldehydes and Ketones

 The boiling points of aldehydes and ketones are
intermediate between those of alcohols and alkanes
 The polarity of the carbonyl groups enables aldehyde
and ketone molecules to interact with each other
through dipole-dipole interactions
 Aldehyde and ketones can't form hydrogen bonds
with each other
 They can only form hydrogen bond with
water
 Lower-molecular-mass aldehydes and ketones are
soluble in water
 Aldehyde + water = hydrogen bond
 Ketone + water = hydrogen
 Thus, if you were going to boil aldehyde
with water, the boiling point will be higher
than boiling aldehyde alone

Chemical of Aldehydes and Ketones

Oxidation of an aldehyde to give a carboxylic acid
 Catalyst: Potassium Permanganate/ Potassium
Dichromate

Nomenclature of Ketones
1. Select as the parent carbon chain the longest carbon
chain that includes the carbon atom of the carbonyl
group
2. Name the parent chain by changing the -e ending of Attempted oxidation of a ketone
the corresponding alkane name to -one  Not readily oxidized because of the location
3. Number the carbon chain such that the carbonyl  Terminal carbonyl groups are more susceptible to
carbon atom receives the lowest possible number. oxidation than inner carbonyl groups
The position of the carbonyl carbon atom is noted by
 4. Lecture on Organic Chemistry Part 3
Reduction of an aldehyde to give a primary alcohol
Reduction of a Ketone to give a secondary alcohol
Hemiacetal
 Compound where carbon atom is bonded to both a
hydroxyl –OR
 Very important in sugars
 Formation of closed ring structures
 Formation of closed ring structures
 The oxygen at the end of the straight
chained sugar will attack the carbon at the
other end → bonding
 Oxygen= Nucleophile
 Hydrogen= Electrophile
Acetal
 Compound with a carbon atom bonded to two
alkoxy groups (-OR)
Addition of an alcohol to an aldehyde to form a hemiacetal
and then an acetal
 Aldehyde + Alcohol (R-O-H) = Hemiacetal
 etal
Hydrolysis of an acetal to yield an aldehyde and two
alcohols
 Somewhat a decomposition reaction
 Separates the components of the reactants
 Acetal + water = Aldehyde + Alcohol + Alcohol
SUMMARY : CHEMICAL PROPERTIES OF ALDEHYDES AND
KETONES
Oxidation of Aldehydes and Ketones
Tollen's Test
 Solution of Tollen's test contains AgNO3 and NH3 in
water
 Aldehyde in the presence of silver nitrate will result
to the formation of a carboxylic acid and a silver
metal
 Positive Test Result: Silver Mirror
Silver mirror will indicate the presence of aldehyde, pag
ketone ang dinagdag sa AgNO3; it will not produce a silver
mirror
Benedict's Test
 Used in testing of sugars in urine
 Solution is made by dissolving copper sulfate,
sodium citrate, and sodium carbonate in water
 Aldehyde will bind with copper to form a carboxylic
acid
 Copper is the oxidizing agent
 Positive Test Result: Brick-red precipitation
 Sodium Carbonate- provides alkaline conditions
which are required for the redox reaction
 Sodium Citrate- acts as complexing agent which
keeps the copper in the solution, since it would
otherwise precipitate
Glucose determination
 Glucose- the only monosaccharide utilized by the
body for different biochemical processes
 Diabetic Px- do not produce sufficient insulin
 Insulin- important in the transportation of oxygen S
ugars, such as glucose, are polyhydroxyl aldehydes
 Oxidation reaction of glucose will form carboxylic
acid and hydrogen peroxide
 Positive Test Result: Glucometer detects
hydrogen peroxide
 Enzyme is used as catalyst
4. Lecture on Organic Chemistry Part 3