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[PDF] Generic Functional Group Pattern in ordero of nomenclature priority

prefix when lower priority functional group: 1o amides: prefix: RCN RCHO RCOR' RCONR'R" nitrile aldehyde ketone 2o amide 3o amide R O R S R N

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Functional Group Interconversion by Substitution, Including

Section 3 2 discusses the use of SN 2 reactions for various functional group of the ester derived from 3-hydroxymethyl-3- methyloxetane 272 RCOR' NH O O

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contrast several topics at one time, such as the types of functional groups As you read RCOR ▷▷ Drop -e and add -one ▷▷ ▷Add number at beginning to

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compounds in terms of their functional group and solubility behavior The ketone functional group can be condensed to R(C=O)R or RCOR, in which R is 

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Functional Groups REACTIONS

23.1 Introduction to

Functional Groups

E ssential Understanding Most organic compounds contain chemically reactive components called functional groups.

Reading

Strategy

Compare and Contrast Organizing information in a table helps you compare and contrast several topics at one time, such as the types of functional groups. As you read, ask yourself, "How are they similar? How are they different?" As you read Lesson 23.1, use the compare and contrast table below to differentiate among functional groups. Compound typeGeneral structureFunctional group halocarbonR - X (X = F, Cl, Br, or I)halogen EXTENSION Write an example for each type of compound based on ethane (C 2 H 6 alcoholR - OHhydroxy etherR - O - Rether amineR - NH 2 amino aldehyde O

R - C - H

carbonyl ketone O

R - C - R

carbonyl carboxylic acid O

R - C - OH

carboxyl ester O

R - C - O - Rester

amide O R

R - C - N - R

amide

Examples: C

2 H 5 Cl, C 2 H 5

OH, (C

2 H 5 2 O, C 2 H 5 NH 2 , C 2 H 4 O, (C 2 H 5 2

CO, CH

3 COOH, CH 3 COOCH 2 CH 3 , and CH 3 CONH

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Lesson

summary Functional Groups A functional group is a chemically functional part of an organic compound. Substituents called functional groups are often attached to hydrocarbon chains or rings. ɀ Organic compounds can be classified according to their functional groups.ɀ Halocarbons A halocarbon is an organic compound that contains a halogen as its functional group. The general formula of a halocarbon is RX, where X is a halogen substituent.ɀ When a halogen is attached to an aliphatic chain, it is called an alkyl halide; when ɀ attached to an arene ring, it is an aryl halide. Common names of halocarbons begin with the name of the alkyl or aryl group and end ɀ with the name of the halogen with an -ide ending. substitution Reactions A substitution reaction can be used to introduce functional groups into organic compounds. A halocarbon is produced when a halogen atom replaces a hydrogen atom on an alkane. ɀ A catalyst, such as iron, is often used in the halogenation of aromatic compounds.ɀ Halocarbons can be converted to other halocarbons, amines, or ethers by similar ɀ substitution reactions. type of reactionGeneral reactionspecific reaction

Alkane halogenation

R - H X 2 R - X HXCH 4 Cl 2 CH 3

Cl HCl

Aromatic halogenation

CO x C O H N H N X 2 CO x C O H N H N

X HXCO

x C O H N H N Br 2 CO x C O H N H N

Br HBr

Formation of alcohol

2R - X 2OH

2RĿOH X

CH 3 I

KOH � CH

3

OH KI

after reading Lesson 23.1, complete the following questions.

Functional Groups

1. Is the following sentence true or false? The saturated hydrocarbon skeletons of organic

molecules are chemically reactive.

2. What is a functional group?

It is a specific arrangement of atoms in an organic compound that is capable of characteristic chemical reactions.false

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Use table 23.1 to answer Questions 3 and 4.

3. name the functional group for each general structure.

a. R - o - R b. R - oH c. R - nH 2

4. name two compound types that have a carbonyl group as a functional group.

a. b.

Halocarbons

5. What are halocarbons?

6. Give the iUPac and common names for the following halocarbons.

a. CH 3 - CH 2 - CH 2 - Br b. H H CCI H

7. a halogen attached to a carbon of an aliphatic chain produces a halocarbon called a(n)

8. the second part of a halocarbon common name ends with

9. Highly halogenated organic compounds have higher

because of van der Waal interactions.

10 . What uses do halogenated hydrocarbons have?

11. What is an aryl halide?

Substitution Reactions

12 . Why do reactions involving organic compounds often proceed more slowly than those

involving inorganic molecules and ions?

13 . is the following sentence true or false? the products of organic reactions are often a complex mixture of compounds.

Halocarbons are a class of organic compounds containing covalently bonded fluorine, chlorine, bromine, or iodine. They can be used as refrigerants, as solvents, or as ingredients of elastomers. It is a halocarbon in which a halogen is attached to a carbon of an arene ring.

These reactions commonly involve the breaking of relatively strong covalent bonds.bromopropane, propyl bromide

iodoethene, vinyl iodide alkyl halide -ide boiling pointsether aldehyde ketonehydroxy amino true

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14 . Organic reactions that involve the replacement of one atom or group of atoms with

another atom or group of atoms are called reactions.

15 . Label the compounds in this generalized halogenation reaction.

R - H X 2

R - X HX

16 . Hydroxide ions can displace most halogens on carbon chains to produce a(n)

23.2 Alcohols, Ethers,

and Amines

Essential Understanding

Three of the most important types of compounds with functional groups are alcohols, ethers, and amines.

Lesson Summary

Alcohols Organic compounds with the general formula R - OH are alcohols. Aliphatic alcohols belong to different structural groups according to the number of ɀ carbons attached to the carbon with the hydroxy group. Many alcohols are soluble in water and have high boiling points.ɀ

Naming Alcohols

Type of compoundNaming rulesExample

1 hydroxy group attached to

an alkyl groupɀ

Name longest chain

Drop -e, add -ol

Write number at beginning to show where the OH is attached butanol (OH at end) common name: butyl alcohol

2-hydroxy-butane

2 or 3 hydroxy groups

attached to an alkyl groupɀ

Use numbers

Add endings -diol or -triol1,3-propanediol

1,2,3-propanetriol

Hydroxy group attached

directly to an aromatic ringɀ

Use the word phenol

Place other attached groups before the word phenolmethylphenol diethylphenol Addition Reactions New functional groups can be added to an organic molecule at the site of a double or triple bond. In an addition reaction, a substance is added at the double or triple bond of an alkene or ɀ alkyne. Water and halides can be inserted through hydration or halogenation addition reactions.ɀ A catalyst is used to enable a hydrogen to be added to a carbon-carbon double bond in a ɀ hydrogenation reaction. 2 substitution alcohol alkanehalogenhalocarbonhydrogen halide

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ethers An ether is an organic compound in which oxygen is bonded to two carbon groups with the general formula R - O - R. To form the IUPAC name for an ether, the shorter R group is written with an ɀ-oxy ending, followed by the larger R group name. To form the common name for an ether, the names of the two R groups are listed in ɀ alphabetical order, followed by the word ether. Ethers usually have lower boiling points than comparable alcohols, but higher boiling ɀ points than comparable hydrocarbons. amines When one or more of the hydrogen atoms in ammonia are replaced by carbon groups, the compound is classified as an amine. An amine can be primary, secondary, or tertiary, depending on the number of carbon ɀ groups. In IUPAC naming, the -ɀe ending of the parent hydrocarbon is changed to -amine. The common name of an amine is made by naming the carbon group and adding ɀ -amine. after reading Lesson 23.2, complete the following questions. alcohols

1. What are alcohols?

2. The functional group in an alcohol is called a(n)

group. Match each structural category of aliphatic alcohols with its description.

3. primary alcohola. three R groups attached to C - OH

4. secondary alcoholb. one R group attached to C - OH

5. tertiary alcoholc. two R groups attached to C - OH

6. Circle the letter of the IUPAC ending used for an alcohol with two 2 - OH substitutions.

a. -ol b. -tetrol c. -triol d. -diol 7. is the common name for alcohols with more than one - OH substituent.

8. Write the IUPAC name and the common name for each alcohol shown.

a. CH 3 - CH 2 - OH b. OH CH 3 CH 3 CH c. CH 2 CH 2 CH

OH OH OH

They are a class of organic compounds with an - OH group. hydroxy

Glycol

ethanol; ethyl alcohol

2-propanol; isopropyl alcohol

1,2,3-propanetriol; glycerolb

c a

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9. Is the following sentence true or false? Alcohols cannot form intermolecular hydrogen

bonds.

10 . What are the two parts of an alcohol molecule?

11. Why are alcohols with four or more carbons not soluble in water?

12 . Name two uses for 2-propanol (or rubbing) alcohol.

a. b.

13 . Which alcohol is used in many antifreezes?

14 . The action of yeast or bacteria on sugars to produce ethanol is called

15 . How is ethanol denatured?

Addition Reactions

16 . Adding new functional groups at the double or triple bond of an alkene or alkyne is

called a(n) reaction.

17. Is the following sentence true or false? Adding a hydrogen halide to an alkene results in

a disubstituted halocarbon.

18 . Look at the reaction between ethene and water:

H H

CCOHHH

H H 100
C a. Draw the structure of the product. b. What type of compound is the product? c. What is this type of addition reaction called? d. What is the role of the hydrogen ions? As the number of carbon atoms increases, the nonpolarity of the carbon chain becomes more significant than the polarity of the hydroxy group.

It is used as an antiseptic.

It is used as a base for cosmetics.

1,2-ethanediol

fermentation addition false an alcohol a hydration reaction a catalystA denaturant, usually methyl alcohol, is added to make it toxic. HC HC H H H OH false the carbon chain and the hydroxy group

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19. What type of reaction is used to manufacture solid spreads from cooking oils?

2 0 . Which hydrocarbon resists addition reactions?

Ethers

21. An ether is a compound in which is bonded to two carbon

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