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Chemistry: A Molecular Approach , 1 st Ed. Nivaldo Tro. Chapter 20 Organic Chemistry. Roy Kennedy Massachusetts Bay Community College Wellesley Hills, MA. 2008, Prentice Hall. Structure Determines Properties. Organic compounds all contain carbon

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chapter 20 organic chemistry

Chemistry: A Molecular Approach, 1st Ed.Nivaldo Tro

Chapter 20OrganicChemistry

Roy Kennedy

Massachusetts Bay Community College

Wellesley Hills, MA

2008, Prentice Hall

structure determines properties
Structure Determines Properties
  • Organic compounds all contain carbon
    • CO, CO2 , carbonates and carbides are inorganic
    • other common elements are H, O, N, (P, S)
  • Carbon has versatile bonding patterns
    • chains, rings, multiple bonds
    • chain length nearly limitless
  • Carbon compounds generally covalent
    • molecular; gases, liquids, or low melting solids; varying solubilities; nonconductive in liquid
  • C - C bonds unreactive (very stable)

Tro, Chemistry: A Molecular Approach

allotropes of carbon diamond
Allotropes of Carbon - Diamond

Tro, Chemistry: A Molecular Approach

allotropes of carbon graphite
Allotropes of Carbon - Graphite

Tro, Chemistry: A Molecular Approach

carbon bonding
Carbon Bonding
  • mainly forms covalent bonds
  • C is most stable when it has 4 single covalent bonds, but does form double and triple bonds
    • C=C and C≡C are more reactive than C−C
    • C with 4 single bonds is tetrahedral,
    • 2 singles and 1 double is trigonal planar
    • 2 doubles or 1 triple and 1 single is linear

Tro, Chemistry: A Molecular Approach

hydrocarbons
Hydrocarbons
  • hydrocarbons contain only C and H
    • aliphatic or aromatic
  • insoluble in water
    • no polar bonds to attract water molecules
  • aliphatic hydrocarbons
    • saturated or unsaturated aliphatics
      • saturated = alkanes, unsaturated = alkenes or alkynes
    • may be chains or rings
    • chains may be straight or branched
  • aromatic hydrocarbons

Tro, Chemistry: A Molecular Approach

saturated hydrocarbons
Saturated Hydrocarbons
  • a saturated hydrocarbon has all C-C single bonds
    • it is saturated with hydrogens
  • saturated aliphatic hydrocarbons are called alkanes
  • chain alkanes have the general formula CnH2n+2

Tro, Chemistry: A Molecular Approach

unsaturated hydrocarbons
Unsaturated Hydrocarbons
  • unsaturated hydrocarbons have one of more C=C double bonds or CC triple bonds
  • unsaturated aliphatic hydrocarbons that contain C=C are called alkenes
    • the general formula of a monounsaturated chain alkene is CnH2n
    • remove 2 more H for each additional unsaturation
  • unsaturated aliphatic hydrocarbons that contain CC are called alkynes
    • the general formula of a monounsaturated chain alkyne is CnH2n-2
    • remove 4 more H for each additional unsaturation

Tro, Chemistry: A Molecular Approach

unsaturated hydrocarbons10
Unsaturated Hydrocarbons

Tro, Chemistry: A Molecular Approach

aromatic hydrocarbons
Aromatic Hydrocarbons
  • contain benzene ring structure
  • even though they are often drawn with C=C, they do not behave like alkenes

Tro, Chemistry: A Molecular Approach

slide12

alkanes

alkenes

alkynes

Tro, Chemistry: A Molecular Approach

formulas
Formulas
  • molecular formulas just tell you what kinds of atoms are in the molecule, but they don’t tell you how they are attached
  • structural formulas show you the attachment pattern in the molecule
  • models not only show you the attachment pattern, but give you an idea about the shape of the molecule
condensed structural formulas
Condensed Structural Formulas
  • attached atoms listed in order
    • central atom with attached atoms
  • follow normal bonding patterns
    • use to determine position of multiple bonds
  • () used to indicate more than 1 identical group attached to same previous central atom
    • unless () group listed first in which case attached to next central atom

Tro, Chemistry: A Molecular Approach

line angle formulas
Line-Angle Formulas
  • each angle, and beginning and end represent a C atom
  • H omitted on C
    • included on functional groups
  • multiple bonds indicated
    • double line is double bond, triple line is triple bond

Tro, Chemistry: A Molecular Approach

formulas16
Formulas

Tro, Chemistry: A Molecular Approach

formulas17
Formulas

Tro, Chemistry: A Molecular Approach

isomerism
Isomerism
  • Isomers = different molecules with the same molecular formula
  • Structural Isomers = different pattern of atom attachment
    • Constitutional Isomers
  • Stereoisomers = same atom attachments, different spatial orientation

Tro, Chemistry: A Molecular Approach

structural isomers of c 4 h 10
Structural Isomers of C4H10

Butane, BP = 0°C

Isobutane, BP = -12°C

Tro, Chemistry: A Molecular Approach

rotation about a bond is not isomerism
Rotation about a bond is not isomerism

Tro, Chemistry: A Molecular Approach

possible structural isomers
Possible Structural Isomers

Tro, Chemistry: A Molecular Approach

ex 20 1 write the structural formula and carbon skeleton formula for c 6 h 14
Ex 20.1 – Write the structural formula and carbon skeleton formula for C6H14

Tro, Chemistry: A Molecular Approach

stereoisomers
Stereoisomers
  • stereoisomers are different molecules whose atoms are connected in the same order, but have a different spatial direction
  • optical isomers are molecules that are nonsuperimposable mirror images of each other
  • geometric isomers are stereoisomers that are not optical isomers

Tro, Chemistry: A Molecular Approach

nonsuperimposable mirror images
Nonsuperimposable Mirror Images

mirror image cannot be rotated so all its atoms align

with the same atoms of the original molecule

Tro, Chemistry: A Molecular Approach

chirality
Chirality
  • any molecule with a nonsuperimposable mirror image is said to be chiral
  • any carbon with 4 different substituents will be a chiral center
  • a pair of nonsuperimposable mirror images are called a pair of enantiomers

Tro, Chemistry: A Molecular Approach

optical isomers of 3 methylhexane
Optical Isomers of 3-methylhexane

Tro, Chemistry: A Molecular Approach

plane polarized light
Plane Polarized Light
  • light that has been filtered so that only those waves traveling in a single plane are allowed through

Tro, Chemistry: A Molecular Approach

optical activity
Optical Activity
  • a pair of enantiomers have all the same physical properties except one – the direction they rotate the plane of plane polarized light
    • each will rotate the plane the same amount, but in opposite directions
    • dextrorotatory = rotate to the right
    • levorotatory = rotate to the left
  • an equimolar mixture of the pair is called a racemic mixture
    • rotations cancel, so no net rotation

Tro, Chemistry: A Molecular Approach

chemical behavior of enantiomers
Chemical Behavior of Enantiomers
  • a pair of enantiomers will have the same chemical reactivity in a non-chiral environment
  • but in a chiral environment they may exhibit different behaviors
    • enzyme selection of one enantiomer of a pair

Tro, Chemistry: A Molecular Approach

alkanes
Alkanes
  • aka paraffins
  • aliphatic
  • general formula CnH2n+2for chains
  • very unreactive
  • come in chains or/and rings
    • CH3 groups at ends of chains, CH2 groups in the middle
    • chains may be straight or branched
  • saturated
  • branched or unbranched

Tro, Chemistry: A Molecular Approach

naming
Naming
  • each name consists of 3 parts
    • prefix
      • indicates position, number, and type of branches
      • indicates position, number, and type of each functional group
    • parent
      • indicates the length of the longest carbon chain or ring
    • suffix
      • indicates the type of hydrocarbon
        • ane, ene, yne
      • certain functional groups

Tro, Chemistry: A Molecular Approach

naming alkanes
Naming Alkanes
  • Find the longest continuous carbon chain
  • Number the chain from end closest to a branch
    • if first branches equal distance use next in
  • Name branches as alkyl groups
    • locate each branch by preceding its name with the carbon number on the chain
  • List branches alphabetically
    • do not count n-, sec-, t-, count iso
  • Use prefix if more than one of same group present
    • di, tri, tetra, penta, hexa
    • do not count in alphabetizing
alkyl groups

H

C

H

-

,

M

E

T

H

Y

L

H

C

3

H

H

H

C

H

C

H

-

,

E

T

H

Y

L

H

C

C

3

2

H

H

H

H

H

C

H

C

H

C

H

-

,

P

R

O

P

Y

L

H

C

C

C

3

2

2

H

H

H

H

C

H

3

(

C

H

)

C

H

-

,

I

S

O

P

R

O

P

Y

L

H

C

C

3

2

H

H

Alkyl Groups

Tro, Chemistry: A Molecular Approach

more alkyl groups

H

H

H

H

C

H

C

H

C

H

C

H

-

,

n

-

B

U

T

Y

L

H

C

C

C

C

3

2

2

2

H

H

H

H

H

H

C

H

3

C

H

C

H

(

C

H

)

C

H

-

,

s

e

c

-

B

U

T

Y

L

H

C

C

C

3

2

3

H

H

H

H

C

H

H

3

(

C

H

)

C

H

C

H

-

,

I

S

O

B

U

T

Y

L

H

C

C

C

3

2

2

H

H

H

C

H

3

B

U

T

Y

L

H

C

C

(

C

H

)

C

-

,

tert-

-

3

3

3

C

H

3

More Alkyl Groups

Tro, Chemistry: A Molecular Approach

examples of naming alkanes

H H H H H

H C C C C C H

H CH3 H H H

H CH3 H H H H

H C C C C C C H

H CH3 CH H H H

CH3 CH3

Examples of Naming Alkanes

2-methylpentane

3-isopropyl-2,2-dimethylhexane

Tro, Chemistry: A Molecular Approach

example name the alkane
Example – Name the alkane
  • find the longest continuous C chain and use it to determine the base name

since the longest chain has 5 C

the base name is pentane

Tro, Chemistry: A Molecular Approach

example name the alkane40
Example – Name the alkane
  • identify the substituent branches

there are 2 substituents

both are 1 C chains, called methyl

Tro, Chemistry: A Molecular Approach

example name the alkane41
Example – Name the alkane
  • number the chain from the end closest to a substituent branch
    • if first substituents equidistant from end, go to next substituent in

then assign numbers to each substituent based

on the number of the main chain C it’s attached to

1 2 3 4 5

both substituents are equidistant from the end

2 4

Tro, Chemistry: A Molecular Approach

example name the alkane42
Example – Name the alkane
  • write the name in the following order
    • substituent number of first alphabetical substituent followed by dash
    • substituent name of first alphabetical substituent followed by dash
      • if it’s the last substituent listed, no dash
      • use prefixes to indicate multiple identical substituents
    • repeat for other substituents alphabetically
    • name of main chain

dimethyl

pentane

2,4 –

2 4

Tro, Chemistry: A Molecular Approach

practice name the following
Practice – Name the Following

Tro, Chemistry: A Molecular Approach

practice name the following44
Practice – Name the Following

3-ethyl-2-methylpentane

Tro, Chemistry: A Molecular Approach

drawing structural formulas

1 2 3 4 5 6

Drawing Structural Formulas

4-ethyl-2-methylhexane

  • draw and number the base chain carbon skeleton
  • add the carbon skeletons of each substituent on the appropriate main chain C
  • add in required H’s

Tro, Chemistry: A Molecular Approach

practice draw the structural formula of 4 isopropyl 2 methylheptane
Practice – Draw the structural formula of 4-isopropyl-2-methylheptane

Tro, Chemistry: A Molecular Approach

practice draw the structural formula of 4 isopropyl 2 methylheptane47
Practice – Draw the structural formula of 4-isopropyl-2-methylheptane

Tro, Chemistry: A Molecular Approach

alkenes
Alkenes
  • also known as olefins
  • aliphatic, unsaturated
    • C=C double bonds
  • formula for one double bond = CnH2n
    • subtract 2 H from alkane for each double bond
  • trigonal shape around C
    • flat
  • much more reactive than alkanes
  • polyunsaturated = many double bonds

Tro, Chemistry: A Molecular Approach

alkenes50
Alkenes

ethene = ethylene

propene

Tro, Chemistry: A Molecular Approach

physical properties of alkenes
Physical Properties of Alkenes

Tro, Chemistry: A Molecular Approach

alkynes
Alkynes
  • also known as acetylenes
  • aliphatic, unsaturated
  • CºC triple bond
  • formula for one triple bond = CnH2n-2
    • subtract 4 H from alkane for each triple bond
  • linear shape
  • more reactive than alkenes

Tro, Chemistry: A Molecular Approach

alkynes54
Alkynes

ethyne = acetylene

propyne

Tro, Chemistry: A Molecular Approach

physical properties of alkynes
Physical Properties of Alkynes

Tro, Chemistry: A Molecular Approach

naming alkenes and alkynes
Naming Alkenes and Alkynes
  • change suffix on main name from -ane to -enefor base name of alkene, or to -yne for the base name of the alkyne
  • number chain from end closest to multiple bond
  • number in front of main name indicates first carbon of multiple bond

Tro, Chemistry: A Molecular Approach

examples of naming alkenes

H H H

H C C C C C H

H CH3 H H H

H CH3 H H

H C C C C C C H

H CH3 CH H H H

CH3 CH3

Examples of Naming Alkenes

2-methyl-1-pentene

3-isopropyl-2,2-dimethyl-3-hexene

Tro, Chemistry: A Molecular Approach

examples of naming alkynes

H H H

H C C C C C H

CH3 H H

H CH3 H H

H C C C C C C H

H CH3 CH H

CH3 CH3

Examples of Naming Alkynes

3-methyl-1-pentyne

4-isopropyl-5,5-dimethyl-2-hexyne

Tro, Chemistry: A Molecular Approach

name the alkene
Name the Alkene
  • find the longest, continuous C chain that contains the double bond and use it to determine the base name

since the longest chain with the double bond has 6 C

the base name is hexene

Tro, Chemistry: A Molecular Approach

name the alkene60
Name the Alkene
  • identify the substituent branches

there are 2 substituents

one is a 1 C chain, called methyl

the other one is a 2 C chain, called ethyl

Tro, Chemistry: A Molecular Approach

name the alkene61

3

4

4

3

2

1

5

6

Name the Alkene
  • number the chain from the end closest to the double bond

then assign numbers to each substituent based

on the number of the main chain C it’s attached to

Tro, Chemistry: A Molecular Approach

name the alkene62

3

4

4

3

2

1

5

6

Name the Alkene
  • write the name in the following order
    • substituent number of first alphabetical substituent – substituent name of first alphabetical substituent –
      • use prefixes to indicate multiple identical substituents
    • repeat for other substituents
    • number of first C in double bond – name of main chain

3–ethyl–

4–methyl–

2–hexene

Tro, Chemistry: A Molecular Approach

practice name the following63
Practice – Name the Following

Tro, Chemistry: A Molecular Approach

practice name the following64
Practice – Name the Following

3

4

5

6

2

1

3,4-dimethyl-3-hexene

Tro, Chemistry: A Molecular Approach

name the alkyne
Name the Alkyne
  • find the longest, continuous C chain that contains the triple bond and use it to determine the base name

since the longest chain with the triple bond has 7 C

the base name is heptyne

Tro, Chemistry: A Molecular Approach

name the alkyne66
Name the Alkyne
  • identify the substituent branches

there are 2 substituents

one is a 1 C chain, called methyl

the other one is called isopropyl

Tro, Chemistry: A Molecular Approach

name the alkyne67

7

6

5

4

3

2

1

6

4

Name the Alkyne
  • number the chain from the end closest to the triple bond

then assign numbers to each substituent based

on the number of the main chain C it’s attached to

Tro, Chemistry: A Molecular Approach

name the alkyne68

7

6

5

4

3

2

1

6

4

Name the Alkyne
  • write the name in the following order
    • substituent number of first alphabetical substituent – substituent name of first alphabetical substituent –
      • use prefixes to indicate multiple identical substituents
    • repeat for other substituents
    • number of first C in double bond – name of main chain

4–isopropyl–

6–methyl–

2–heptyne

Tro, Chemistry: A Molecular Approach

practice name the following69
Practice – Name the Following

Tro, Chemistry: A Molecular Approach

practice name the following70
Practice – Name the Following

3

2

1

4

5

3,3-dimethyl-1-pentyne

Tro, Chemistry: A Molecular Approach

geometric isomerism
Geometric Isomerism
  • because the rotation around a double bond is highly restricted, you will have different molecules if groups have different spatial orientation about the double bond
  • this is often called cis-trans isomerism
  • when groups on the doubly bonded carbons are cis, they are on the same side
  • when groups on the doubly bonded carbons are trans, they are on opposite sides

Tro, Chemistry: A Molecular Approach

free rotation around c c
Free Rotation AroundC─C

Tro, Chemistry: A Molecular Approach

cis trans isomerism
Cis-Trans Isomerism

Tro, Chemistry: A Molecular Approach

reactions of hydrocarbons
Reactions of Hydrocarbons
  • all hydrocarbons undergo combustion
  • combustion is always exothermic
    • about 90% of U.S. energy generated by combustion

2 CH3CH2CH2CH3(g) + 13 O2(g) → 8 CO2(g) + 10 H2O(g)

CH3CH=CHCH3(g) + 6 O2(g) → 4 CO2(g) + 4 H2O(g)

2 CH3CCCH3(g) + 11 O2(g) → 8 CO2(g) + 6 H2O(g)

Tro, Chemistry: A Molecular Approach

other alkane reactions
Other Alkane Reactions
  • Substitution
    • replace H with a halogen atom
    • initiated by addition of energy in the form of heat or ultraviolet light
      • to start breaking bonds
    • generally get multiple products with multiple substitutions

Tro, Chemistry: A Molecular Approach

other alkene and alkyne reactions
Other Alkene and Alkyne Reactions
  • Addition reactions
    • adding a molecule across the multiple bond
  • Hydrogenation = adding H2
    • converts unsaturated molecule to saturated
    • alkene or alkyne + H2 → alkane
  • Halogenation = adding X2
  • Hydrohalogenation = adding HX
    • HX is polar
    • when adding a polar reagent to a double or triple bond, the positive part attaches to the carbon with the most H’s
addition reactions
Addition Reactions

Tro, Chemistry: A Molecular Approach

aromatic hydrocarbons78
Aromatic Hydrocarbons
  • contain benzene ring structure
  • even though they are often drawn with C=C, they do not behave like alkenes

Tro, Chemistry: A Molecular Approach

resonance hybrid
Resonance Hybrid
  • the true structure of benzene is a resonance hybrid of two structures

Tro, Chemistry: A Molecular Approach

naming monosubstituted benzene derivatives

propylbenzene

fluorobenzene

Naming Monosubstituted Benzene Derivatives
  • (name of substituent)benzene
    • halogen substituent = change ending to “o”
  • or name of a common derivative

Tro, Chemistry: A Molecular Approach

naming benzene as a substituent

4-phenyl-1-hexene

Naming Benzene as a Substituent
  • when the benzene ring is not the base name, it is called a phenyl group

Tro, Chemistry: A Molecular Approach

naming disubstituted benzene derivatives

1

3

2

2

1,2-dimethylbenzene

1

1-bromo-3-fluorobenzene

Naming Disubstituted Benzene Derivatives
  • number the ring starting at attachment for first substituent, then move toward second
    • order substituents alphabetically
    • use “di” if both substituents the same

Tro, Chemistry: A Molecular Approach

naming disubstituted benzene derivatives83
Naming Disubstituted Benzene Derivatives
  • alternatively, use relative position prefix
    • ortho- = 1,2; meta- = 1,3; para- = 1,4

2-chlorotoluene

ortho-chlorotoluene

o-chlorotoluene

3-chlorotoluene

meta-chlorotoluene

m-chlorotoluene

4-chlorotoluene

para-chlorotoluene

p-chlorotoluene

Tro, Chemistry: A Molecular Approach

practice name the following84
Practice – Name the Following

Tro, Chemistry: A Molecular Approach

practice name the following85
Practice – Name the Following

1-chloro-4-fluorobenzene

1,3-dibromobenzene

or meta-dibromobenzene

or m-dibromobenzene

Tro, Chemistry: A Molecular Approach

polycyclic aromatic hydrocarbons
Polycyclic Aromatic Hydrocarbons
  • contain multiple benzene rings fused together
    • fusing = sharing a common bond

Tro, Chemistry: A Molecular Approach

reactions of aromatic hydrocarbons
Reactions of Aromatic Hydrocarbons
  • most commonly, aromatic hydrocarbons undergo substitution reactions – replacing H with another atom or group

Tro, Chemistry: A Molecular Approach

functional groups
Functional Groups
  • other organic compounds are hydrocarbons in which functional groups have been substituted for hydrogens
  • a functional group is a group of atoms that show a characteristic influence on the properties of the molecule
    • generally, the reactions that a compound will perform are determined by what functional groups it has
    • since the kind of hydrocarbon chain is irrelevant to the reactions, it may be indicated by the general symbol R

CH3—OH

R group

functional group

Tro, Chemistry: A Molecular Approach

alcohols
Alcohols
  • R-OH
  • ethanol = CH3CH2OH
    • grain alcohol = fermentation of sugars
    • alcoholic beverages
      • proof number = 2X percentage of alcohol
    • gasohol
  • isopropyl alcohol = (CH3)2CHOH
    • 2-propanol
    • rubbing alcohol
    • poisonous
  • methanol = CH3OH
    • wood alcohol = thermolysis of wood
    • paint solvent
    • poisonous

Tro, Chemistry: A Molecular Approach

naming alcohols
Naming Alcohols
  • main chain contain OH
  • number main chain from end closest to OH
  • give base name ol ending and place number of C on chain where OH attached in front
  • name as hydroxy group if other higher precedence group present

1

2

3

4

5

6

4-ethyl-4-methyl-3-hex-5-enol

Tro, Chemistry: A Molecular Approach

reactions of alcohols

CH3 OH + HCl ® CH3Cl + H2O

H2SO4

CH3 CH2OH ® CH2 CH2 + H2O

- 2 H

- 2 H

CH3 CH2OH ® CH3 CHO ® CH3 COOH

CH3 OH + Na ® CH3O−Na+ + ½ H2

Reactions of Alcohols

Nucleophilic Substitution

Acid Catalyzed Elimination (Dehydration)

Oxidation

with Reactive Metals

Tro, Chemistry: A Molecular Approach

aldehydes and ketones

formaldehyde

acetone

Aldehydes and Ketones
  • contain the carbonyl group
  • aldehydes = at least 1 side H
  • ketones = both sides R groups
  • many aldehydes and ketones have pleasant tastes and aromas
  • some are pheromones
  • formaldehyde = H2C=O
    • pungent gas
    • formalin = a preservative
    • wood smoke, carcinogenic
  • acetone = CH3C(=O)CH3
    • nail-polish remover

Tro, Chemistry: A Molecular Approach

aldehyde odors and flavors
Aldehyde Odors and Flavors
  • butanal = butter
  • vanillin = vanilla
  • benzaldehyde = almonds
  • cinnamaldehyde = cinnamon
ketone odors and flavors
Ketone Odors and Flavors
  • acetophenone = pistachio
  • carvone = spearmint
  • ionone = raspberries
  • muscone = musk
reactions
Reactions
  • aldehydes and ketones are generally synthesized by the oxidation of alcohols
  • therefore, reduction of an aldehyde or ketone results in an alcohol

Tro, Chemistry: A Molecular Approach

carbonyl group
Carbonyl Group

C=O group is highly polar

many reactions involve addition across C=O,

with positive part attached to O

Tro, Chemistry: A Molecular Approach

addition to c o
Addition to C=O

Tro, Chemistry: A Molecular Approach

carboxylic acids
Carboxylic Acids
  • RCOOH
  • sour tasting
  • weak acids
  • citric acid
    • found in citrus fruit
  • ethanoic acid = acetic acid
    • vinegar
  • methanoic acid = formic acid
    • insect bites and stings

Tro, Chemistry: A Molecular Approach

carboxylic acids100
Carboxylic Acids
  • made by the oxidation of aldehydes and alcohols
    • OH on the end of the chain
  • always on main chain
    • has highest precedence
  • C of group always C1
    • position not indicated in name
  • change ending to oic acid

Tro, Chemistry: A Molecular Approach

naming carboxylic acids
Naming Carboxylic Acids

Tro, Chemistry: A Molecular Approach

esters

methyl butanoate

aspirin

Esters
  • R–COO–R
  • sweet odor
  • made by reacting carboxylic acid with an alcohol

RaCOOH + RbOH  RaCOORb + H2O

  • name alkyl group from alcohol, then acid name with oate ending
    • precedence over carbonyls, but not carboxylic acid
    • number from end with ester group

Tro, Chemistry: A Molecular Approach

naming esters
Naming Esters

Tro, Chemistry: A Molecular Approach

condensation reactions

esters are made by the condensation reaction

  • between a carboxylic acid and an alcohol
          • the reaction is acid catalyzed
  • acid anhydrides are made by the condensation
  • reaction between 2 carboxylic acid molecules
          • the reaction is driven by heat
Condensation Reactions
  • a condensation reaction is any organic reaction driven by the removal of a small molecule, like water

Tro, Chemistry: A Molecular Approach

synthesis of aspirin acetylsalicylic acid
Synthesis of Aspirin(Acetylsalicylic Acid)

Tro, Chemistry: A Molecular Approach

ethers
Ethers
  • R– O – R
  • ether = diethyl ether = CH3CH2OCH2CH3
    • anesthetic
  • to name ethers, name each alkyl group attached to the O, then add the word ether to the end

diethyl ether

Tro, Chemistry: A Molecular Approach

amines
Amines
  • N containing organic molecules
  • very bad smelling
  • form when proteins decompose
  • organic bases
  • name alkyl groups attached to the N, then add the word amine to the end

putrescine

ethylamine

ethylmethylamine

cadaverine

Tro, Chemistry: A Molecular Approach

amines108
Amines
  • many amines are biologically active
    • dopamine – a neurotransmitter
    • epinephrine – an adrenal hormone
    • pyridoxine – vitamin B6
  • alkaloids are plant products that are alkaline and biologically active
    • toxic
    • coniine from hemlock
    • cocaine from coca leaves
    • nicotine from tobacco leaves
    • mescaline from peyote cactus
    • morphine from opium poppies

Tro, Chemistry: A Molecular Approach

amine reactions
Amine Reactions
  • weak bases
    • react with strong acids to form ammonium salts

RNH2 + HCl → RNH3+Cl−

  • react with carboxylic acids in a condensation reaction to form amides

RCOOH + HNHR’  RCONHR’ + H2O

Tro, Chemistry: A Molecular Approach