CHAPTER TWELVE: ORG COMP W/OXYGEN AND SULFUR

Question 1

What is an ALCOHOL?

Answer 1

a class of organic compound that contains an oxygen atom.

a hydroxyl group (-OH) replaces a hydrogen atom in a hydrocarbon.

Question 2

What is a PHENOL?

Answer 2

a class of organic compound that contains an oxygen atom.

a hydroxyl group (-OH) replaces a hydrogen atom attached to a benzene ring.

Question 3

What is a THIOL?

Answer 3

contains a sulfur atom, which makes a thiol similar to an alcohol except that -OH is replaced by -SH.

Question 4

What is an ETHER?

Answer 4

an oxygen atom is attached to 2 carbon atoms by single bonds.

Question 5

Molecules of ALCOHOLS, PHENOLS, THIOLS AND ETHERS have _____ shapes

Answer 5

bent shapes around the oxygen or sulfur atom, similar to water.

Question 6

In the IUPAC system, an alcohol is named by replacing the “e” of the corresponding alkane name with _____.

Answer 6

“ol”

Question 7

The common name of a simple alcohol uses the name of the alkyl group followed by __________.

Answer 7

alcohol

Question 8

Alcohols with 1 or 2 carbon atoms ________ (do/do not) require a number for the hydroxyl group.

Answer 8

do not

Question 9

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 __________.

Answer 9

-OH; substituents

Diol

Question 10

In the IUPAC system, THIOLS are named by adding _________ to the longest carbon chain connected to the -SH group.

Answer 10

thiol

Question 11

What is an important property of THIOLS?

Answer 11

Their strong, sometimes disagreeable, odor .

Question 12

In the IUPAC system, how are ETHERS named?

Answer 12

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.

Question 13

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?

Answer 13

alkyl group

• primary- has one alkyl group attached
• secondary- two groups
• tertiary- three groups

Question 14

Are alcohols and ethers soluble in water? Why or why not?

Answer 14

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.

Question 15

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.

Answer 15

any amount of the alcohol is completely soluble in water.

Decreases

Five

Question 16

Ethers with up to __ carbon atoms are slightly soluble in water.

Answer 16

4

Question 17

PHENOL is ______ soluble in water because ____________.

Answer 17

slightly; the -OH group can form hydrogen bonds with water molecules.

Question 18

Describe the process of the DEHYDRATION OF AN ALCOHOL.

Answer 18

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

Question 19

In organic chemistry, what is an OXIDATION reaction? What is a REDUCTION reaction?

Answer 19

Oxidation- an increase in the number of carbon-oxygen bonds.

Reduction- fewer bonds between carbon and oxygen.

Question 20

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.

Answer 20

ALDEHYDE; double

[O]

H20

Question 21

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.

Answer 21

Ketones; hydrogen

ketone; double

Question 22

TERTIARY ALCOHOLS do not oxidize readily because __________

Answer 22

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.

Question 23

THIOLS also undergo oxidation when there is a loss of ______ atoms from each of two ______ groups.

The oxidized product contains a ____ bond.

Answer 23

hydrogen; -SH groups

disulfide (-S-S-)

Question 24

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 _______.

Answer 24

dipole

aldehydes and ketones

Question 25

In an ALDEHYDE, the carbon of the carbonyl group is bonded to at least ______ hydrogen atom(s), which may also be bonded to ____, ______ or _________.

Answer 25

one; another hydrogen atom; a carbon of an alkyl group or an aromatic ring

Question 26

In a KETONE, the carbonyl group is bonded to ____ alkyl groups or aromatic rings.

Answer 26

two.

Question 27

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?

Answer 27

"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)

Question 28

Naming KETONES: * common names * IUPAC system

Answer 28

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.

Question 29

ALDEHYDES and KETONES contain a polar _________ group (carbon-oxygen double bond), which has a partially ________ oxygen atom and a partially ______ carbon atom.

Answer 29

carbonyl negative; positive

Question 30

Are ALDEHYDES and KETONES soluble?

Answer 30

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.

Question 31

PRIMARY ALCOHOLS can oxidize to ALDEHYDES. ALDEHYDES are easily oxidized further to _________ ______. Do KETONES undergo further oxidation?

Answer 31

carboxylic acids NO

Question 32

What is TOLLENS' TEST?

Answer 32

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.

Question 33

What is BENEDICT'S TEST?

Answer 33

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.

Question 34

ALDEHYDES and KETONES are reduced by _____ ________.

Answer 34

sodium borohydrde (NaBH4)

Question 35

In the REDUCTION of organic compounds, there is a _____ in the number of carbon-oxygen bonds by the ______ of hydrogen or the _____ of oxygen.

Answer 35

decrease; addition; loss

Question 36

ALDEHYDES reduce to _____ alcohols and KETONES reduce to _____ alcohols.

Answer 36

primary; secondary

Question 37

Is a catalyst needed for the addition of hydrogen to the carbonyl group?

Answer 37

yes

Question 38

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 _______ ___ _____.

Answer 38

identical; same; arranged in space

Question 39

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 ________.

Answer 39

"handedness" Chiral Achiral See page 434 for the explanation and diagram of this.

Question 40

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.

Answer 40

at least one carbon atom two different ways

Question 41

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.

Answer 41

two

Question 42

What is a FISCHER PROJECTION MODEL? Vertical lines represent _____. Horizontal lines represent _____. The intersection of vertical and horizontal lines represents ________.

Answer 42

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