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New Jersey Center for Teaching and Learning

Progressive Science Initiative

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Organic Chemistry

Carbon and the Molecular Diversity of Life

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Organic chemistry is the chemistry of carbon compounds.

Carbon is the backbone of biological molecule

Carbon has the ability to form long chains.

Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form.

Organic Chemistry

Stearate C17H36O2

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Organic compounds range from simple molecules to colossal ones

Most organic compounds contain hydrogen atoms in addition to carbon atoms

Organic Chemistry

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Carbon has four valence electrons to make covalent bonds

Carbon atoms can form diverse molecules by bonding to four other atoms

Electron configuration is the key to an atom’s characteristics

Electron configuration determines the kinds and number of bonds an atom will form with other atoms

Organic Chemistry

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1 Organic chemistry is a science based on the study of A functional groups.B vital forces interacting with matter.C carbon compounds.D water and its interaction with other

kinds of molecules.E inorganic compounds.

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2 Which property of the carbon atom gives it compatibility with a greater number of different elements than any other type of atom?

A Carbon has 6 to 8 neutrons.

B Carbon has a valence of 4.

C Carbon forms ionic bonds.

D A and C only

E A, B, and C

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3 How many electron pairs does carbon share in order to complete its valence shell?

A 1

B 2

C 4

D 6

E 8

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4 What type/s of bond/s does carbon have a tendency to form?

A Ionic

B Hydrogen

C Covalent

D A and B

E A, B and C

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5 Organic chemistry is currently defined as

A the study of compounds that can be made only by living cells.

B the study of carbon compounds.

C the study of vital forces.

D the study of natural (as opposed to synthetic) compounds.

E the study of hydrocarbons.

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Hydrocarbons are compounds made up of carbon and hydrogen atoms. There are two major categories: Aliphatic and Aromatic

Aliphatic hydrocarbons : compounds with carbon atoms connected in a straight chainAliphatic compounds consist of three classes of compounds:· Alkanes· Alkenes· Alkynes

Aromatic hydrocarbons : compounds with carbon atoms connected to form cyclic structure and with an aroma (smell or odor)

Hydrocarbons

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Hydrocarbon chains made up of all SINGLE carbon bonds

They are also known as saturated hydrocarbons

They are “saturated” with hydrogens

Name uses the ending -ane

Examples: Methane, Propane, Butane, Octane

Aliphatic hydrocarbon: Alkanes

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The general formula CnH2n+2

n = number of carbon atoms

Hexane

Heptane

Octane

Nonane

Decane

CH4 Methane

C2H6 Ethane

C3H8 Propane

C4H10 Butane

C5H12 Pentane

Formula NameFormula Name

(The students can fill this)

Aliphatic hydrocarbon: Alkanes

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Aliphatic hydrocarbon: Alkanes

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Hydrocarbons are non polar. All C-H bonds are nonpolar. As the number of electrons in the molecule increases ( larger molecules), it would be easily polarizable and hence the LD forces increases. This increases the bpt. of the higher alkanes.

Aliphatic hydrocarbon: Alkanes

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Straight chain alkanes: An alkane that has all its carbons connected in a row.

CH3-CH2-CH3

Branched chain alkanes: An alkane that has a branching connection of carbons.

CH3-CH-CH2-CH3

CH3

Aliphatic hydrocarbon: Alkanes

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Alkanes: Ethane

Structural formula Condensed formula

Branched chain

CH3 - CH3

C C

H

H

H

H

H

H

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Alkanes

Branched chain

Pentane Isopentane

Neopentane

CH3 - CH(CH3) - CH2 - CH3CH3 - CH2 - CH2 - CH2 - CH3

C(CH3)4

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6 What is the reason why hydrocarbons are not soluble in water?

A The majority of their bonds are polar covalent carbon to hydrogen linkages

B The majority of their bonds are nonpolar covalent carbon to hydrogen linkages

C They are hydrophilic

D They exhibit considerable molecular complexity and diversity

E They are lighter than water

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Alkenes

Alkenes have at least one 1 double bond between two carbon atoms.

General formula: CnH2n

The name uses the ending -ene

The first member would be C2H4 - Ethene (from 2 carbon parent, ethane)C3H6 - Propene Ethene

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Alkyne general formula: CnH2n-2

They must have at least one triple bondThe name uses the ending -yne

C2H2 Ethyne or commonly known as acetylene

C3H4 Propyne or propylene

Alkynes

Ethyne

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Ball and stickmodel

Space fillingmodel

Molecular formula

Structuralformula

Aliphatic hydrocarbons

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Cycloalkanes

Carbon can also form ringed structures.

Five and six-membered rings are most stable.

They can take on conformations in which their bond angles are very close to the tetrahedra angle.

Smaller rings are quite strained

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Aromatic hydrocarbonsThey have benzene ring structure (hexagon) and a particular aroma.

CH3

Benzene Toluene (methyl benzene)

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7 Hydrocarbons

A are polar.

B are held together by ionic bonds.

C contain nitrogen.

D contain only hydrogen and carbon atoms.

E are held together by hydrogen bonds.

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8 Which of the following hydrocarbons has a double bond in its carbon skeleton?

A C3H8

B C2H6

C CH4

D C2H4

E C2H2

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9 The gasoline consumed by an automobile is a fossil fuel consisting mostly of

A aldehydes

B amino acidd

C alcohols

D hydrocarbons

E thiols

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10 Hydrocarbons containing only single bonds between the carbon atoms are called __________.

A alkenes

B alkynes

C aromatics

D alkanes

E ketones

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11 Which is the formula of an alkane?

A C10H10

B C10H18

C C10H20

D C10H22

E C10H24

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12 Hydrocarbons containing carbon-carbon triple bonds are called________.

A alkenes

B alkynes

C aromatics

D alkanes

E ketones

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13 Which is the formula of an alkyne?

A C10H10

B C10H18

C C10H20

D C10H22

E C10H24

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14 The molecular geometry of each carbon atom in an alkane is ________.

A octahedral

B square planar

C trigonal planar

D tetrahedral

E trigonal pyramidal

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15 The general formula of an alkane is _______.

A C2nH2n+2

B CnH2n

C CnH2n+2

D CnH2n-2

E CnHn

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16An alkene has at least one ________ and has the general formula ______.

A C-C single bond, CnH2n+2

B C-C double bond, CnH2n

C C-C triple bond, CnH2n

D C-C double bond, CnH2n-2

E C-C triple bond, CnH2n-2

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17 The compound below is an _________.

A alkyne

B alkene

C alkane

D aromatic compound

E olefin

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18 Gasoline and water do not mix because gasoline is __________.

A less dense than water

B less viscous than wtaer

C nonpolar and water is polar

D volatile and water is not

E polar and water is nonpolar

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19 Which substance would be the most soluble in gasoline?

A water

B NaNO3

C HCl

D hexane

E NaCl

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20 ________ could be the formula of an alkene.

A C3H8

B C3H6

C C6H6

D C17H36

E CH8

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Hydrocarbons exhibit a phenomenon called isomerism- existence of different molecular arrangement but same formula.

Isomers are compounds with the same molecular formula but different structures and properties:

Structural isomers have different covalent arrangements of their atoms

Geometric isomers have the same covalent arrangements but differ in spatial arrangements

Enantiomers are isomers that are mirror images of each other

Isomers

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Structural Isomers

Isomers

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cis isomer: The two CH3 are on the same side.

trans isomer: The two CH3 are on opposite sides.

Geometric Isomers

Isomers

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Enantiomers differ in spatial arrangement around an asymmetric carbon, resulting in molecules that are mirror images, like left and right hands. The two isomers are designated the L and D isomers from the Latin for left and right (levo and dextro). Enantiomers cannot be superimposed on each other.

Enantiomers are isomers that arenonsuperimposable mirror images

Isomers

Enantiomers (optical isomers)

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Bond Angle at Each C Atom

Alkane Alkene Alkyne

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21 Structural isomers are molecules that

A are enantiomers.B are hydrocarbons.C have a ring structure.D are mirror images.E differ in the covalent arrangements of

their atoms.

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22 The two molecules shown here are best described as

A optical isomers

B radioactive isotopes

C structural isomers

D nonradioactive isotopes

E geometric isomers

CH3 - CH2 -O-H

CH3-O-CH3

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Which of the following is true of geometric isomers?

They have variations in arrangement around a double bond.

They have an asymmetric carbon that makes them mirror images.

They have the same chemical properties.

They have different molecular formulas.

Their atoms and bonds are arranged in different sequences

23

A

B

C

D

E

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24The two molecules shown below are best described as

A optical isomers.B radioactive isotopes.C structural isomers.D nonradioactive isotopes.E geometric isomers.

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1. Find and name the longest continuous carbon chain. This is called the parent chain. (Examples: methane, propane, etc.)

2. Number the chain consecutively, starting at the end nearest an attached group (substituent).

3. Identify and name groups attached to this chain. (Examples: methyl-, bromo-, etc.)

4. Designate the location of each substituent group with the number of the carbon parent chain on which the group is attached. Place a dash between numbers and letters. (Example: 3-chloropentane)

5. Assemble the name, listing groups in alphabetical order. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. Place a comma between multiple numbers. (Example: 2,3-dichloropropane)

Naming Organic Compounds

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Naming Organic CompoundsWhere is the longest continuous chain of carbons?

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Naming Organic Compounds

Number the parent chain so that the attached groups are on the lowest numbers.

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· Carbon (alkyl) groups· Methyl CH3 -· Ethyl CH3CH2-· Propyl CH3CH2CH2 –· Halogens· Fluoro (F-)· Chloro (Cl-)· Bromo (Br-)· Iodo (I-)

Naming Organic CompoundsNames of attached groups/substituents

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Naming Organic Compounds

1,1,1-trichloro-1-fluoromethane 1,1-dichloro-1,1-difluoromethane

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Naming Organic Compounds

3-ethylhexane

2,2-dimethylbutane

2,3-dimethylbutane

Draw the structures

CH3

CH3

CH3 CH2CH CH2

Name the compounds below

CH3

CH3

CH3 CH CH2CH

CH3

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IN A TIE, halogens get the lower number before alkyl groups

Naming Organic Compounds

4-chloro-2-methylpentane or2-chloro-4-methylpentane?

4-bromo-2-chloropentane or 2-bromo-4-chloropentane ?

IN A TIE between SIMILAR GROUPS, the group lower ALPHABETICALLY gets the lower number

CH3

CH3

CH3 CH2CH CH

Cl

Cl

H3C

Br

CH3

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IUPAC nomenclature rules for alkenes and alkynes are similar to alkanes.

Step 1. Name the parent compound. Find the longest chain containing the double or triple bond, and name the parent compound by adding the suffix –ene or –yne to the name of the main chain.

Naming Organic Compounds

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Naming Organic Compounds

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Naming Organic Compounds

CH2=CHCH2CH3 1-butene but-1-ene

CH3CH=CHCH3 2-butene but-2-ene

CH3C CCH3 2-butyne but-2-yne

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Write the IUPAC name for each of the following unsaturated compounds:

A. CH3CHC CCH3

CH3

B. CH3C=CHCH3

Naming Organic Compounds

C.

CH3

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Double bond is fixed

Cis/trans Isomers are possible

CH3 CH3 CH3

CH = CH CH = CH cis trans CH3

Naming Organic Compounds

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Many aromatic compounds are common in nature and in medicine.

Naming Organic Compounds

COOCH3

COOH

OCH3

OH

CHO

COOH

CH3

CH

CH3

CH3 -CH-CH2

aspirinvanillin

ibuprofen

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Naming Organic CompoundsAromatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene.

No number is needed for mono-substituted benzene since all the ring positions are identical.

Cl CH3

chlorobenzene methylbenzene/toluene

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When two groups are attached to benzene, the ring is numbered to give the lower numbers to the side groups. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used

Naming Organic Compounds

CH3

CH3

Cl

ClCH3

Cl

1,2 dmethylbenzeneOrtho-dimethylbenzene

1,3 dichlorobenzenemeta-dichlorobenzene

1-chloro- 4-methyl benzene para- chloromethylbenzene

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Write the structural formulas for each of the following:

A. 1,3-dichlorobenzene

B. Ortho-chlorotoluene

Naming Organic Compounds

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Functional Groups

Haloalkanes/alkenes/alkynesAlcohols/Thiols AcidsAminesKetonesAldehydesEstersEther

A functional group is an atom or group of atoms that imparts special physical and chemical properties to the compoundBased on the functional group, the compounds are classified as follows.

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Halo- alkanes/alkenes/alkynes

Presence of a Halogen atom (F, Cl, Br or I)

CH3Cl, CH2Cl2 , CHCl3, CCl4, F2C=CF2 , FC = CF

They are formed when one or more H atoms are replaced by halogen atom/s

CH3CH2CH2CH CH3

Cl

CH3CH2CH2C CH2

Cl

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Alcohols and Thiols

The functional group is a hydroxyl group, -OH

If O is replaced by a S atom, it is called a thiol -SH

Thiol is the same as sulfhydride

OH- - hydroxyl groupSH- - sulfhydryl group

In CH4, if one H is replaced by -OH

The name ends with -ol, drop the alkane "e" add "ol"

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Ethane becomes ethyl alcohol or ethanol

Alcohols and Thiols

OHC

H

H

H

OHC

H

HH

H C

H

Methane becomes methyl alcohol or Methanol

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25 A compound contains hydroxyl groups as its predominant functional group. Which of the following statements is true concerning this compound? A It lacks an asymmetric carbon, and it

is probably a fat or lipid.B It should dissolve in water.

C It should dissolve in a nonpolar solvent.

D It won't form hydrogen bonds with water.

E It is hydrophobic.

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26 Which of the structures contain(s) a hydroxyl group?

A A

B B

C CD C & E

E None of the structures

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27 In which of the structures are the atoms bonded ionic bonds?

A A

B BC CD C, D, EE None of the structures

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Acids or Carboxylic Acids

The functional group is -COOH

Replace one H atom in the alkane by a -COOH group

HCOOH = Methanoic acid or formic acidCH3COOH = Ethanoic acid or acetic acid or vinegar

CH3CH2COOH = Propanoic acid

Drop the "e" from the parent alkane and add " oic acid"

COOH COOH

ethane di-carboxylic acid or oxalic acid

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AminesThe functional group is - NH2

CH3NH2 Replace one H by an -NH 2 group

CH3NH2 Amino methane or Methyl amine

More than one functional groups, same or different are common in organic compounds

example: amino acids. They have amine and acid groups

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What is the name of the functional group shown in the following figure?

carbonyl

ketone

aldehyde carboxyl

hydroxyl

28

A

B

C

D

E

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Which two functional groups are always found in amino acids?

ketone and aldehyde

carbonyl and carboxyl

carboxyl and amino

phosphate and sulfhydryl

hydroxyl and aldehyde

29

A

B

C

D

E

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KetonesThe functional group is -C=O or "carbonyl" group and isusually sandwiched between two carbon groups.

CH3CH2CH3 = propaneCH3CO CH3 propanone or acetone ( nail polish remover)Drop e and add none

H3C- C- CH3

CH3COC2H5 Ethyl methyl ketone or butanone

O

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Ketones

Estrogen- has two hydroxyl groups in it.

Testosterone - one hydroxyl group is replaced by a ketone.Theproperty and function of the molecules changes.

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Aldehydes

The functional group is -CHO with a C=O bond

drop 'e' of the parent alkane and add 'nal'

HCHO - (1 carbon) Methanal or Formaldehyde

CH3CHO - (2 carbon) Ethanal or Acetaldehyde

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Aldehydes, Ketones and AcidsThe way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes

The C=O is between two other carbon atoms ( alkyl groups) in the molecule

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Aldehydes, Ketones and Acids

The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes

The C=O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom

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Aldehydes, Ketones and Acids

The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes

The C=O bond should be connected to an OH group

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What is the name of the functional group shown in the following figure?

30

ABCDE

R-C=O

R

(R = any carbon group)

carbonyl ketone aldehyde carboxyl hydroxyl

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31 Draw the structure of propanoic acid

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EsterThe functional group is -COOR where R could be another alkyl group

Esters are formed by the combination of an acid and an alcohol by eliminating one molecule of water.

They are usually pleasant smelling compounds (natural oils and essence)

CH3COOH + CH3OH --> CH3COOCH3

CH3COOCH3 - methyl acetate

CH3COOC2H5 - ethyl acetate

C2H5COOCH3 - methyl propanoate

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Ether

The functional group is an O atom sandwiched between two carbon groups.

CH3-O- CH3 dimethyl ether

They are highly flammable and used as solvents in organic synthesis

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Groups with a Carbon–Oxygen Double Bond (Carbonyl Groups)

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Amides

Amides are formed by the reaction of carboxylic acids with amines.

RCOOH + H2NR' --> -H2O

CONH linkage is known as the amide linkage (peptide) in proteins.

This linkage is formed when several amino acids join with their acid and amino groups together.

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32 Which is the best description of a carbonyl group? A an oxygen joined to a carbon by a

single covalent bondB a nitrogen and two hydrogens joined

to a carbon by covalent bonds

C a carbon joined to two hydrogens by single covalent bonds

D a sulfur and a hydrogen joined to a carbon by covalent bonds

E a carbon atom joined to an oxygen by a double covalent bond

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33What is the name of the functional group shown below. A carbonylB ketoneC aldehydeD carboxylE hydroxyl

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34 Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen?

A an alcohol such as ethanolB a monosaccharide such as glucoseC a steroid such as testosteroneD an amino acid such as glycineE a hydrocarbon such as benzene

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35What type of functional group is shown in the compound below?

A carbonylB ketoneC aldehydeD carboxylE hydroxyl

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36

A B C

D E

Which molecule contains an amine functional group?

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37

A B C

D E

Which molecule contains an aldehyde functional group?

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38

A B C

D E

Which molecule contains an alcohol functional group?

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39 Which one of the following is not an alcohol?

A acetone

B glycerol

C ethanol

D cholesterol

E ethylene glycol

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MacromoleculesMarcromolecules are large molecules composed of smaller molecules.

They have complex structures

Carbon has the unique property of joining together via covalent bonding to form large (macro) molecules. Most macromolecules are polymers, built from monomers

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Macromolecules

In living things, three major classes of organic molecules are polymers

Proteins Carbohydrates Nucleic acids

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Although organisms share the same limited number of monomer types, each organism is unique based on the arrangement of monomers into polymers

An immense variety of polymers can be built from a small set of monomers

Polymers

Polymer Made of these monomers

Proteins Amino acids

Carbohydrates Simple sugars (monosaccharides)

Nucleic acids Nucleotides

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The Synthesis and Breakdown of Polymers

Monomers form larger molecules by condensation reactions called dehydration reactions

PolymersIs a long molecule consisting of many similar building blocks called monomers

longer polymer

Monomershort polymer

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The Synthesis and Breakdown of Polymers

Polymers

longer polymer

Monomershort polymer

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Amino Acids and ProteinsProteins are formed when several amino acids combine together.

Acid and amine end of the molecules join together to form long peptide chain.

Peptide chain with 50 or more amino acids can form an individual protein.

Peptide Chain

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Carbohydrates/SugarsSimple sugars are poly-hydroxy aldehydes or ketones.Table sugar, (sucrose) is made up of glucose and fructose.They all have several hydroxyl groups in their structure that makes them soluble in water. Sugars are otherwise known as saccharides.

C

Glucose Fructose

(Monosaccharide)

Glucose and fructose are monosaccharides.

Sucrose is a disaccharide.

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In solution, carbohydrates form cyclic structures.

They can form chains of sugars that form structural molecules such as starch and cellulose.

Not all sugars are sweet.

Carbohydrates/Sugars

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Nucleic AcidsNucleic acids are made up of monomer units called nucleotides.

Sugar + Base + PO43- = nucleotide

A nucleotide is made up of 3 components:a 5-carbon sugar (ribose or deoxyribose) + a nitrogenous base + a phosphate group, PO 4

3-

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Sugars

Bases

Two of the building blocks of RNA and DNA are sugars (ribose or deoxyribose) and cyclic bases (adenine, guanine, cytosine, and thymine or uracil)

Nucleic Acids

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Nucleic Acids

RNA DNA

Ribonucleic acid Deoxyribonucleic acid

Contains the sugar ribose Contains the sugar deoxyribose

Uses bases A, C, G and U Uses bases A, C, G and T

Function is to make proteins Function is to carry genetic code

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Nucleotides combine to form the familiar double-helix form of the nucleic acids

The blue ribbon is the sugar/phosphate backbone

The bases are the rungs in the (spiral) ladder

The nucleotides join together via hydrogen bonding through their bases: A-T, C-G etc.

Nucleic Acids

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40 Which of the following is not one of the four major groups of macromolecules found in living organisms?

A glucoseB carbohydratesC lipids

D proteins

E nucleic acids

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41 Glucose is a type of _______.

A amino acidB proteinC carbohydrateD nucleotideE nucleic acids

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42Nucleic acids are made up of __________.

A amino acidsB proteinsC carbohydratesD nucleotidesE sugars

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43 A nucleotide consists of _____________.

A glucose + fructose + amino acidB glucose + fructose + phosphate groupC amino acid + protein + phosphate group

D sugar + base + amino acidE sugar + base + phosphate group

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44 Polymers of polysaccharides and proteins are all synthesized from monomers by which process?

A connecting monosaccharides together (condensation reactions)

B the addition of water to each monomer (hydrolysis)

C the removal of water (dehydration reactions)

D ionic bonding of the monomers

E the formation of disulfide bridges between monomers

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Other Complex Molecules of Life

Fats and Lipids are another major category of molecules found in living things.

They are a diverse group of hydrophobic molecules and, unlike the other macromolecules, are not made up of polymers.

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Fats and lipids are constructed from two types of smaller molecules, a single glycerol and usually three fatty acids.

Carboxylic acids have a very long chain of carbon atoms and v ary in the length and number and locations of double bonds they contain.

Fats and Lipids

A fatty acid

CH2OH

CH2OH

CH2OH

Glycerol

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Attachment of fatty acids to glycerol

Fats and Lipids

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Fats and Lipids3 fatty acids added to glycerol producing a fat molecule

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Saturated fatty acids:

have the maximum number of hydrogen atoms possible

have no double bonds in their carbon chain animal origin

Fats and Lipids

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Unsaturated fatty acids

have one or more double bonds

when hydrogenated (more hydrogens are added) they become solid and saturated mainly plant origin

Fats and Lipids

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Phospholipids: have only two fatty acidshave a phosphate group instead of a third fatty acidresults in a bilayer arrangement found in cell membranes

Fats and Lipids

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Steroids are lipids characterized by a carbon skeleton consisting of three or more fused rings.

Cholesterol

Fats and Lipids

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45 Which of the following is (are) true for the class of large biological molecules known as lipids? A They are insoluble in water.

B They are an important constituent of cell membranes.

C They provide the least amount of energy in living organisms

D Only A and B are correct.

E A, B, and C are correct.

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46 Saturated fatty acids

A are the predominant fatty acid in corn oil.

B have double bonds between carbon atoms of the fatty acids.

Chave a higher ratio of hydrogen to carbon than do unsaturated fatty acids.

D are usually liquid at room temperature.

E are usually produced by plants.

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47 The hydrogenation of vegetable oil would result in which of the following?

Aa decrease in the number of carbon-carbon double bonds in the oil (fat) molecules

Ban increase in the number of hydrogen atoms in the oil (fat) molecule

C the oil (fat) being a solid at room temperature

D A and C only

E A, B, and C

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