Organic and Biochemistryorganic chemistry:

-- molecular shape is crucial

3-D structure ofsalicylic acid

3-D structure ofacetylsalicylic acid

(asp

irin)

the study of carbon-containing compounds

biochemistry: the chemistry of living things

Carbon is unique amongthe elements because:

it can have up to four bonds per C atom --

single, double, or triple bonds

--

--

it can form REALLY long chains of C atoms

its bonds are strong

–C–C– C=C –C=C–

Basic Definitions

hydrocarbons: compounds containing only __ and __

alkanes: hydrocarbons having only ______ bonds single

-- ALKANES = FUEL

–C–C–C–

–C–

H H

HHH

H

HHHH

–C–C–C–C–

H H HH

H HH H HH

H C

-- very stable; no rxn w/acids, bases, strong oxidizers

-- –anes are saturated

structural isomers: same molecular formula, different…bonding arrangements

alkenes: hydrocarbons having at least one ____ bond C=C

alkynes: hydrocarbons having at least one ____ bond C=C

C=CH

C

H

HH H

H

H–C–C=C–C–C–C–H

H

H

H H H

H H H

CH2CHCH3

CH3CC(CH2)2CH3

The simplest alkyne,ethyne (i.e., acetylene)– C2H2 – is the fuel in oxyacetylene torches.

aromatic hydrocarbons: benzene and compounds w/a benzene-related structure

-- –enes, –ynes,and aromaticsare __________ unsaturated

6 C atoms in a planar ringw/“tweener” bonds (C6H6)

August Kekule(1829–1896), whoclaimed that a dreamgave him insight into the structure of benzene.

“Finer-Point” Definitions

Straight-chain compounds have…

a single carbon backbone.

Branched-chain compounds have…

a main carbon backboneAND one or more branches

Substituted compounds have…

one or more H atomsremoved, with otheratoms in their place(s)(often halogens) Br

CH3(CH2)3CH3

C8H18

C5H11Br

C5H12

CH3CH2CH2CH2CH3

Branches and H-replacing atoms/groupsare collectively called… substituents.

–C–C–C–C–C–C–

HCl

HH

HCl

HH

HCl

HHPolyvinylchloride (PVC) is a material

made of long-chain carbons that havemany chloride substituents.

Functional group: a characteristic pattern that makes up a portion of a larger m’cule

-- specific atoms, specific bonding arrangements

-- importance: fgs largely determine the behaviorof their m’cules

–OH

alcohols ketones carboxylic acids

–C–

=

O

–C–

=

O

OH

-- several examples of fgs:

O O

OH

–COOH

Many organic compoundsare combinations ofseveral categories.

Cl

OH

Cl

O

OH

O Br

C6H11Br

Brsub.

br. + sub.

C10H21Cl

fg + sub.

C6H13OCl

fg

C6H12O2

fg + sub. + br.

C9H17OBr

Organic Nomenclature

Memorize the prefixes that tellthe # of C atoms in a chain.

1 =2 =3 =4 =5 =6 =7 =8 =9 =

10 =

meth–eth–prop–but–pent–hex–hept–oct–non–dec–

pent–

non–

dec–

hept–

Naming Straight-Chain Alkanes

1. Find the longest continuous chain of C atoms. Choose the appropriate prefix.

2. The name ends with –ane.

Provide the counterpart to the given.

propane

heptane

(C3H8)

(C7H16)

Alkanes: modification for substituent hydrocarbon (HC) groups

1. Number the “longest chain” carbons. Start with the end nearest a branch.

2. Name and give the #ed location of each substituent.

-- HC substituent groups use the prefixes, but end in –yl.

3. List substituents in alphabetical order.

(i.e., branches)

Provide each counterpart.

4-ethyl-2-methylhexane

octane

1

2

3

4

5

6

7

8

5-ethyl-3-methyl

(C11H24)

(C9H20)

Alkanes: modification for non-HC substituents

1. The “longest chain” MUST contain the substituent.

-- example substituents:

–NO2 –NH2 –F –Br –I nitro amino fluoro bromo iodo

2. Number the chain carbons, starting with the end nearest a substituent.

-- A non-HC substituent takes precedence over an HC branch.

3. Name and give the #ed location of each substituent.

-- If necessary, choose #s so that their sum is as low as possible.

Provide each counterpart.

3-bromo-2-chlorohexane

heptane

2-methyl-1-nitrobutane

heptane2-amino-6-nitro-3-propyl

2-ethyl-1,1-diiodo I

I

Cl

Br

NO2

NH2 NO2

Alkanes: modification for cycloalkanes

-- Use the cyclo- prefix before the word “alkane.”

Provide each counterpart.

1-bromo-1-chloro-2-methylcyclopentane

ethyl

Br

Cl

(C6H10BrCl)

(C8H16)

cyclohexane