CHAPTER TWELVE: ORG COMP W/OXYGEN AND SULFUR Flashcards
What is an ALCOHOL?
a class of organic compound that contains an oxygen atom.
a hydroxyl group (-OH) replaces a hydrogen atom in a hydrocarbon.
What is a PHENOL?
a class of organic compound that contains an oxygen atom.
a hydroxyl group (-OH) replaces a hydrogen atom attached to a benzene ring.
What is a THIOL?
contains a sulfur atom, which makes a thiol similar to an alcohol except that -OH is replaced by -SH.
What is an ETHER?
an oxygen atom is attached to 2 carbon atoms by single bonds.
Molecules of ALCOHOLS, PHENOLS, THIOLS AND ETHERS have _____ shapes
bent shapes around the oxygen or sulfur atom, similar to water.
In the IUPAC system, an alcohol is named by replacing the “e” of the corresponding alkane name with _____.
“ol”
The common name of a simple alcohol uses the name of the alkyl group followed by __________.
alcohol
Alcohols with 1 or 2 carbon atoms ________ (do/do not) require a number for the hydroxyl group.
do not
When an alcohol consists of a carbon chain with 3 or more carbon atoms, the chain is numbered to give the position of the ____ and any ______ of the carbon chain.
When an alcohol contains 2 -OH groups, it is named as a __________.
-OH; substituents
Diol
In the IUPAC system, THIOLS are named by adding _________ to the longest carbon chain connected to the -SH group.
thiol
What is an important property of THIOLS?
Their strong, sometimes disagreeable, odor .
In the IUPAC system, how are ETHERS named?
The name of alkyl or aromatic group attached to the oxygen atom is written in alphabetical order, followed by the word “ether”. In this text, use only the common names of ethers.
ALCOHOLS are classified by the number of ______ groups attached to the carbon atom bonded to the hydroxyl (-OH) group.
What is a:
- primary (1 w/degree sign) alcohol?
- secondary (2 degree) alcohol?
- tertiary (3 degree) alcohol?
alkyl group
- primary- has one alkyl group attached
- secondary- two groups
- tertiary- three groups
Are alcohols and ethers soluble in water? Why or why not?
Yes
The polar -OH group in an alcohol can form hydrogen bonds with the H and O atoms of water.
The electronegative O atom in ethers can also form hydrogen bonds with water.
Alcohols with 1-3 carbon atoms are MISCIBLE which means _______________.
The solubility provided by the -OH group _______ as the number of carbon atoms increases.
Alcohols with ____ or more carbon atoms are insoluble.
any amount of the alcohol is completely soluble in water.
Decreases
Five
Ethers with up to __ carbon atoms are slightly soluble in water.
4
PHENOL is ______ soluble in water because ____________.
slightly; the -OH group can form hydrogen bonds with water molecules.
Describe the process of the DEHYDRATION OF AN ALCOHOL.
During the dehydration of an alcohol:
- H- and -OH are removed from adjacent carbon atoms of the same alcohol to produce a water molecule
- A double bond forms between the same two carbon atoms to produce an ALKENE product.
See diagrams on page 420
In organic chemistry, what is an OXIDATION reaction? What is a REDUCTION reaction?
Oxidation- an increase in the number of carbon-oxygen bonds.
Reduction- fewer bonds between carbon and oxygen.
The oxidation of a PRIMARY ALCOHOL produces an _________, which contains a ________ bond between carbon and oxygen.
To indicate the presence of an oxidizing agent, the symbol ______ is written over the arrow.
An oxidation reaction is balanced with _______, which assumes an oxygen atom is obtained from the oxidizing agent.
ALDEHYDE; double
[O]
H20
In the oxidation of SECONDARY ALCOHOLS, the products are ________. Two _____ atoms are removed.
The result is a ______ that has the carbon-oxygen ______ bond attached to alkyl (CH3) groups on both sides.
Ketones; hydrogen
ketone; double
TERTIARY ALCOHOLS do not oxidize readily because __________
because there is no hydrogen atom on the carbon bonded to the -OH group.
Because C-C bonds are usually too strong to oxidize, terry alcohols resist oxidation.
THIOLS also undergo oxidation when there is a loss of ______ atoms from each of two ______ groups.
The oxidized product contains a ____ bond.
hydrogen; -SH groups
disulfide (-S-S-)
The carbonyl group consists of a carbon-oxygen double bond. The double bond is similar to that of alkenes, except the carbonyl group has a _________.
The _______ of the carbonyl group strongly influences the physical and chemical properties of _______ and _______.
dipole
aldehydes and ketones
In an ALDEHYDE, the carbon of the carbonyl group is bonded to at least ______ hydrogen atom(s), which may also be bonded to ____, ______ or _________.
one; another hydrogen atom; a carbon of an alkyl group or an aromatic ring
In a KETONE, the carbonyl group is bonded to ____ alkyl groups or aromatic rings.
two.
In the IUPAC system, an aldehyde is named by replacing the “e” of the corresponding alkane name with _____.
Is a number needed for the aldehyde group?
“al”
No-it always appears at the end of the chain.
NOTE: the first 4 aldehydes are often referred to by their common names which end in “aldehyde” (formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde)
Naming KETONES:
- common names
- IUPAC system
Common names for unbranched ketones- the alkyl groups bonded to the carbonyl group are named as substituents and are listed alphabetically, followed by “ketone”.
IUPAC-replace the “e” in the corresponding alkane name with “one”. Carbon chains with 5 carbon atoms or more are numbered from the end nearer the carbonyl group.
In a cyclic ketone, the carbonyl carbon is numbered as carbon 1 and the ring is numbered in the direction to give substituents the lowest possible numbers.
ALDEHYDES and KETONES contain a polar _________ group (carbon-oxygen double bond), which has a partially ________ oxygen atom and a partially ______ carbon atom.
carbonyl
negative; positive
Are ALDEHYDES and KETONES soluble?
Yes- the electronegative oxygen atom forms hydrogen bonds with water molecules.
However, if they have 5 or more carbon atoms they are NOT soluble (longer hydrocarbon chains are non polar and diminish the solubility effect of the polar carbonyl group.
PRIMARY ALCOHOLS can oxidize to ALDEHYDES.
ALDEHYDES are easily oxidized further to _________ ______.
Do KETONES undergo further oxidation?
carboxylic acids
NO
What is TOLLENS’ TEST?
Tollens’ test uses a solution of Ag+ and ammonia to oxidize aldehydes but not ketones. The silver ion is reduced and forms a “silver mirror” on the inside of the container.
What is BENEDICT’S TEST?
Gives a positive results with compounds that have an aldehyde functional group and an adjacent hydroxyl group.
The test is negative with simple aldehydes and ketones.
Can also be used to determine the presence of GLUCOSE in blood or urine.
ALDEHYDES and KETONES are reduced by _____ ________.
sodium borohydrde (NaBH4)
In the REDUCTION of organic compounds, there is a _____ in the number of carbon-oxygen bonds by the ______ of hydrogen or the _____ of oxygen.
decrease; addition; loss
ALDEHYDES reduce to _____ alcohols and KETONES reduce to _____ alcohols.
primary; secondary
Is a catalyst needed for the addition of hydrogen to the carbonyl group?
yes
Molecules are structural isomers when they have the same molecular formula but different bonding arrangements.
Another group of isomers, called STEREOISOMERS have ______ molecular formulas but they are not structural isomers. The atoms are bonded in the ____ sequence but differ in the way they are _______ ___ _____.
identical; same; arranged in space
When STEREOISOMERS have mirror images that are different, they are said to have ______.
When organic molecules have mirror images that cannot be completely matched, we say they are NONSUPERIMPOSABLE. Objects such as hands that have NONSUPERIMPOSABLE mirror images are _______.
When a mirror image can be superimposed on the other, the object is ________.
“handedness”
Chiral
Achiral
See page 434 for the explanation and diagram of this.
A carbon compound is CHIRAL if it has _______ carbon atom(s) bonded to four different atoms or groups.
This type of carbon atom is called a CHIRAL CARBON because there are ___ different ways that it can bond to four atoms or groups of atoms.
at least one carbon atom
two different ways
If ____ or more atoms bonded to a caron atom are the same, the atoms can be aligned (superimposed) and the mirror images represent the same structure.
two
What is a FISCHER PROJECTION MODEL?
Vertical lines represent _____.
Horizontal lines represent _____.
The intersection of vertical and horizontal lines represents ________.
A simplified system for drawing stereoisomers that shows the arrangements of the atoms. It represents a 3-dimensional structure.
Vertical= bonds that project backward from a carbon atom
Horizontal= bonds that project forward from a carbon atom.
Intersection= a carbon atom with the most highly oxidized carbon at the top.
See page 437-8
