organic chemistry.....aim 3

what are organic functional groups?

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HW From textbook “CHEMISTRY a Contemporary Approach”

 

Organic acids, alcohols, esters, aldehydes, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds. 

 

Use table R to learn the different organic functional groups.

 

Halide

Organic compounds containing halogens (group 17)

Example

 

 

H

 

Br

 

H

 

H

 

 

 

 

 

 

 

 

 

Cl

 

 

 

 

 

 

 

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

 

 

|

 

 

 

 

 

 

H

—

C

—

C

—

C

—

C

—

H

 

 

 

 

 

Cl

—

C

—

Cl

 

 

 

 

 

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

 

 

|

 

 

 

 

 

 

 

 

H

 

Br

 

H

 

H

 

 

 

 

 

 

 

 

 

Cl

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

2,2-dibromobutane

 

 

 

 

tetrachloromethane

 

 

 

 

 

CH3CBr2CH2CH3

 

 

 

 

 

 

 

CCl4

 

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following halides

1-chloropentane

2-bromo-3-iodohexane

4-chloro-1,1-difluorodecane

1,1,1-trichloro-3,3-difluorononane

 

Alcohol

The (-OH) group is called an hydroxyl group. Under ordinary conditions no more than one -OH group can be attached to one carbon. Alcohols are NOT bases.

Example

 

 

H

 

 

 

 

 

 

H

 

OH

 

H

 

H

 

H

 

H

 

 

 

 

|

 

 

 

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

 

H

—

C

—

OH

 

 

H

—

C

—

C

—

C

—

C

—

C

—

C

—

H

 

 

|

 

 

 

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

 

 

 

H

 

 

 

 

 

 

H

 

H

 

OH

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

methanol

 

 

 

 

2,3-hexanediol

 

 

CH3OH

 

 

 

 

 

CH3CH(OH)CH(OH)CH2CH2CH3

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following alcohols

ethanol

1-butanol

1,2,3-propanetriol

4-decanol

 

Ether

Ethers are generally less reactive than other organic compounds containing oxygen. The first anesthetic used in medical procedures was diethyl ether (CH3CH2OCH2CH3)

Example

 

 

H

 

H

 

H

 

 

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

|

 

|

 

|

 

 

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

 

H

—

C

—

C

—

C

—

O

—

C

—

C

—

C

—

C

—

H

 

 

 

 

 

 

 

 

|

 

|

 

|

 

 

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

 

 

 

H

 

H

 

H

 

 

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

propyl butyl ether

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

CH3CH2CH2OCH2CH2CH2CH3

 

 

 

 

 

 

 

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following ethers

dimethyl ether

ethyl hexyl ether

dipropyl ether

pentyl methyl ether

 

Aldehyde

Aldehydes have peasant odors therefore they are used in the making of perfumes.

Example

 

 

H

 

H

 

O

 

 

 

 

 

 

H

 

H

 

H

 

H

 

O

 

 

 

 

 

|

 

|

 

| |

 

 

 

 

 

 

|

 

|

 

|

 

|

 

| |

 

 

 

H

—

C

—

C

—

C

—

H

 

 

H

—

C

—

C

—

C

—

C

—

C

—

H

 

 

 

|

 

|

 

 

 

 

 

 

 

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

H

 

H

 

 

 

 

 

 

 

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

propanal

 

 

 

 

 

 

pentanal

 

 

 

 

CH3CH2CHO

 

 

 

 

 

CH3CH2CH2CH2CHO

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following aldehydes

methanal

ethanal

heptanal

octanal

 

Ketone

Ketones are found in many natural materials. Acetone, CH3COCH3 is used in nail polish remover.

Example

 

 

H

 

H

 

H

 

H

 

O

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

 

|

 

|

 

|

 

|

 

| |

 

|

 

|

 

|

 

|

 

|

 

 

 

 

H

—

C

—

C

—

C

—

C

—

C

—

C

—

C

—

C

—

C

—

C

—

H

 

 

 

 

|

 

|

 

|

 

|

 

 

 

|

 

|

 

|

 

|

 

|

 

 

 

 

 

 

H

 

H

 

H

 

H

 

 

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

5-decanone

 

 

 

 

 

 

 

 

 

 

CH3CH2CH2CH2COCH2CH2CH2CH2CH3

 

 

 

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following ketones

propanone

4-decanone

3-hexanone

butanone

 

Organic acid

The -COOH group is called a carboxyl group. Organic acids are weak electrolytes.

Example

 

 

O

 

 

 

 

 

 

 

H

 

O

 

 

 

 

 

| |

 

 

 

 

 

 

 

|

 

| |

 

 

 

H

—

C

—

OH

 

 

 

H

—

C

—

C

—

OH

 

 

 

 

 

 

 

 

 

 

 

|

 

 

 

 

 

 

 

 

 

 

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

methanoic acid

 

 

 

 

ethanoic acid

 

 

CHCOOH

 

 

 

 

CH3COOH

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following organic acids

propanoic acid

butanoic acid

hexanoic acid

pentanoic acid

 

Ester

Most esters have sweet and fruity aromas and they are used for substitutes of natural products.

Example

 

 

H

 

H

 

H

 

O

 

 

 

H

 

H

 

H

 

H

 

 

 

 

|

 

|

 

|

 

| |

 

 

 

|

 

|

 

|

 

|

 

 

H

—

C

—

C

—

C

—

C

—

O

—

C

—

C

—

C

—

C

—

H

 

 

|

 

|

 

|

 

 

 

 

 

|

 

|

 

|

 

|

 

 

 

 

H

 

H

 

H

 

 

 

 

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

butyl butanoate

 

 

 

 

 

 

 

 

 

 

CH3CH2CH2COOCH2CH2CH2CH3

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following esters

ethyl ethanoate

methyl propanoate

butyl pentanoate

propyl hexanoate

 

Amine

Amines are related to ammonia. They are the organic version of bases. Amines can be primary, secondary, and tertiary.

Example

A primary amine has only one C attached to N

 

 

H

 

H

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

|

 

 

 

H

—

C

—

C

—

C

—

C

—

C

—

C

—

N

—

H

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

H

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

hexanamine

 

 

 

 

 

 

 

CH3CH2CH2CH2CH2CH2NH2

 

 

 

 

A secondary amine has two C attached to N

 

 

H

 

H

 

H

 

H

 

 

 

H

 

 

 

 

 

|

 

|

 

|

 

|

 

 

 

|

 

 

 

H

—

C

—

C

—

C

—

C

—

N

—

C

—

H

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

 

 

 

 

H

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

methylbutanamine

 

 

 

 

 

CH3CH2CH2CH2NHCH3

 

 

A tertiary amine has three C attached to N

 

 

H

 

 

 

H

 

 

 

 

 

 

 

 

 

 

 

|

 

 

 

|

 

 

 

 

 

 

 

 

 

H

—

C

—

N

—

C

—

H

 

dimethylmethanamine

 

 

|

 

|

 

|

 

 

 

(CH3)3N

 

 

H

 

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

H

—

C

—

H

 

 

 

 

 

 

 

 

 

 

 

 

 

|

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

H

 

 

 

 

 

 

 

 

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following amines

methanamine

ethylethanamine

methylpropanamine

ethylmethylbutanamine

 

Amide

This functional group is called "peptide linkage" by biologists.

Example

 

 

H

 

H

 

H

 

H

 

H

 

H

 

O

 

H

 

 

 

 

|

 

|

 

|

 

|

 

|

 

|

 

| |

 

|

 

 

H

—

C

—

C

—

C

—

C

—

C

—

C

—

C

—

N

—

H

 

 

|

 

|

 

|

 

|

 

|

 

|

 

 

 

 

 

 

 

 

H

 

H

 

H

 

H

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

heptanamide

 

 

 

 

 

 

CH3CH2CH2CH2CH2CH2CONHH

 

 

 

 

 

 

 

H

 

H

 

H

 

O

 

H

 

H

 

H

 

 

 

 

 

 

|

 

|

 

|

 

| |

 

|

 

|

 

|

 

 

 

 

H

—

C

—

C

—

C

—

C

—

N

—

C

—

C

—

H

 

 

 

 

|

 

|

 

|

 

 

 

 

 

|

 

|

 

 

 

 

 

 

H

 

H

 

H

 

 

 

 

 

H

 

H

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

ethylbutanamide

 

 

 

 

 

 

CH3CH2CH2CONHCH2CH2CH3

 

 

 

 

Problems

Draw the structural formula and write the condensed structural formula of the following amides

hexanamide

ethylpropanamide

butylbutanamide

methylpentanamide

 

TEST YOUR UNDERSTANDING

1/07

23 Which structural formula represents an unsaturated hydrocarbon?

 

6/07

19 What is the total number of carbon atoms in a molecule of ethanoic acid? (1) 1 (2) 2 (3) 3 (4) 4

20 Given the formulas for two compounds:

These compounds differ in (1) gram-formula mass    (2) molecular formula    (3) percent composition by mass  (4) physical properties at STP

21 A double carbon-carbon bond is found in a molecule of  (1) pentane (2) pentene (3) pentyne (4) pentanol

45 Which compound is an unsaturated hydrocarbon?  (1) hexanal (2) hexane (3) hexanoic acid (4) hexyne

46 The organic compound represented by the condensed structural formula CH3CH2CH2CHO is classified as an  (1) alcohol (2) aldehyde (3) ester (4) ether

72 Propane is a fuel that is sold in rigid, pressurized cylinders. Most of the propane in a cylinder is liquid, with gas in the space above the liquid level. When propane is released from the cylinder, the propane leaves the cylinder as a gas. Propane gas is used as a fuel by mixing it with oxygen in the air and igniting the mixture, as represented by the balanced equation below.

C3H8(g) + 5O2(g) ---> 3CO2(g) + 4H2O(l) + 2219.2 kJ

A small amount of methanethiol, which has a distinct odor, is added to the propane to help consumers detect a propane leak. In methanethiol, the odor is caused by the thiol functional group (–SH). Methanethiol, CH3SH, has a structure that is very similar to the structure of methanol.

Draw a structural formula for a molecule of methanethiol.

8/07

Base your answers to questions 64 through 66 on the information below.

The incomplete equation below represents an esterification reaction. The alcohol reactant is represented by X.

64 On the structural formula, circle the acid functional group, only.

65 Write an IUPAC name for the reactant represented by its structural formula in this equation.

66 Draw the structural formula for the alcohol represented by X.

1/06

28 Which structural formula is correct for 2-methyl-3-pentanol?

    

44 Given the structural formula:

This compound is classified as an (1) amide (2) amine (3) aldehyde (4) alcohol

6/06

45 Given the formula:

This compound is classified as    (1) an aldehyde (2) an amide (3) an amine (4) a ketone

Base your answers to questions 71 and 72 on the information below.

A thiol is very similar to an alcohol, but a thiol has a sulfur atom instead of an oxygen atom in the functional group. One of the compounds in a skunk’s spray is 2-butene-1-thiol. The formula of this compound is shown below.

71 Explain, in terms of composition, why this compound is a thiol.

72 Explain, in terms of electron configuration, why oxygen atoms and sulfur atoms form compounds with similar molecular structures.

8/06

17 The compounds 2-butanol and 2-butene both contain    (1) double bonds, only (2) single bonds, only (3) carbon atoms (4) oxygen atoms

20 Which organic compound is a saturated hydrocarbon?    (1) ethyne (2) ethene (3) ethanol (4) ethane

Base your answers to questions 78 and 79 on the information below.

Many esters have distinctive odors, which lead to their widespread use as artificial flavorings and fragrances. For example, methyl butanoate has an odor like pineapple and ethyl methanoate has an odor like raspberry.

78 In the space in your answer booklet, draw a structural formula for the ester that has an odor like pineapple.

79 What is a chemical name for the alcohol that reacts with methanoic acid to produce the ester that has an odor like raspberry?

1/05

22 Which organic compound is unsaturated? (1) 2-methylbutane (2) 2-chloropropane (3) 2-hexanol (4) 2-pentene

44 Given the structural formula:

This structural formula represents a molecule of  (1) an aldehyde (2) an ester (3) a ketone (4) an amino acid

6/05

47 Given the structural formula:

The compound represented by this formula can be classified as an (1) organic acid (2) ether (3) ester (4) aldehyde

1/04

15 What is the IUPAC name of the compound with the following structural formula?

 

            (1) propanone (2) propanal (3) butanone (4) butanal

21 The functional group -COOH is found in (1) esters (2) aldehydes (3) alcohols (4) organic acids

6/04

23 Which compound is a saturated hydrocarbon? (1) hexane (2) hexene (3) hexanol (4) hexanal

25 Which of these compounds has chemical properties most similar to the chemical properties of ethanoic acid?    (1) C3H7COOH (2) C2H5OH (3) C2H5COOC2H5 (4) C2H5OC2H5

47 Which structural formula represents an ether?

8/04

44 Given the three organic structural formulas shown below:

Which organic-compound classes are represented by these structural formulas, as shown from left to right?

                1) ester, organic acid, ketone (3) ketone, aldehyde, alcohol   2) ester, aldehyde, organic acid (4) ketone, organic acid, alcohol

65 Draw the structural formula for butanoic acid.

1/03

Which type of organic compound is represented by the structural formula shown below? (1) aldehyde       (2) alcohol    (3) ether    (4) ester

6/03

44. Given the formulas of four organic compounds:

Which pair below contains an alcohol and an acid? (1) a and b (2) a and c (3) b and d (4) c and d

Base your answers to questions 55 and 56 on the information below.

Diethyl ether is widely used as a solvent.

55. Draw the structural formula for diethyl ether.

56. Draw the structural formula for an alcohol that is an isomer of diethyl ether.

8/03

24 Given the structural formulas for two organic compounds:

 

The differences in their physical and chemical properties are primarily due to their different
            (1) number of carbon atoms (3) molecular masses (2) number of hydrogen atoms (4) functional groups

47 Which structural formula represents an alcohol?

 

6/02

1. Which compound is classified as a hydrocarbon?  (1) ethane              (2) ethanol             (3) chloroethane             (4) ethanoic acid

2.  Which pair of compounds are alcohols?

8/02

1. Given the ester: ethyl butanoate

a) Draw the structural formula for this ester.

b) Determine the gram formula mass of this ester.

2.  Which compound is an alcohol?  (1) propanal      (2) ethyne     (3) butane       (4) methanol

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