ORGANIC CHEMISTRY

Alkanes

Alkenes Alkynes

CyclicStructures

Functional Groups

Ring Structures

Branches –Substituents

Chain Structures

TERMS

HYDROCARBONS

ORGANIC CHEMISTRY

carbon containing molecules

carbon & hydrogen molecules

BONDING PATTERNS/REQUIREMENTSBONDING PATTERNS/REQUIREMENTS

Hydrogen (1) Nitrogen (3) Oxygen (2) Halogens (1) carbon (4) X = F, Cl, Br, I

H N..

N..

N:

O.. ..

O..

..

X ..: ..

C

C

C

C

Nitrogen Ion, N+, (4) N+

ORGANIC NOMENCLATURE

alkANE

Single bond between all carbon atoms pg 131

Fromula: CnH2n+2

alkENE

Double bond (at least 1) between carbon atoms

Formula: CnH2n

alkYNE

Triple bond (at least 1) between carbon atoms

“Carbon to Carbon” -- bond identification

Formula: CnH2n-2

# C’s - ane - ene - yne

If structure is a substituent (branch)“yl” ending: methyl; butyl; hexyl

DRAWINGS

Line

Structural

Condensed

Skeletal

PREFIX --- PARENT -- SUFFIX

substituent # ofcarbons Family

-- ane-- ene-- yne

BASIC NAME PATTERNChain molecules

ORGANIC CHEMISTRY

name endingname endingsingle bond: -anedouble bond: -enetriple bond: -ynebranch (substituent): -yl

R, R group: carbon chain

# C single bond double bond triple bond 1 methane 2 ethane ethene ethyne 3 propane propene propyne 4 butane butene butyne

5 & more, use prefix for number (5, pent-; 6, hex-; 7, hept-; etc)

NAMING HYDROCARBONS

1. Find longest continuous carbon chain -- Parent2. Count from end closest to 1st branch -- Prefix3. Family, base bond type -- Suffix

Prefix - Parent - Suffix

“-” dashes bet. # & name

“,” comma bet. numbers & name

CH3

CHCH3 CH2 CH2

CH31

234

5

1

2 3 4

5

branchmethyl

off of C#4 CH3

CHCH3 CH2 CH2

CH3branchmethyl

off of C#2

Parent: 5 C’s, pent

Family: single bonds, Suffix; -anePrefix: branch, C#2 1C: methyl

2-Methylpentane

C

C C C C C

CC1

2 3 4 5 6

7

Name:

C C

C

C CC1 2 3 4 5

=: double bond, functional group, needs to be named & identified where

Name:

CH3

C CH2

CH

H2

CH2 CH3

CH2CH2

CH3

Name:

H2C

CH3

CH2

CH2CH2

CH3

C CH CH3

Name:

If same branch occurs more than once in same molecule; use 2-di, 3-tri, 4-tetra, etc.

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3

name:

If same branch occurs more than once in same molecule; use 2-di, 3-tri, 4-tetra, etc.

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3|CH3

name:

2

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3|CH3

Name:

H

O

2

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3|CH3

Name:

O

2

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3

Name:

O

HO

Name:

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3

OH

Name:

CH2

H3C CH2CH

CHCH2

CH3

CH3

CH3

OH

Name:

FUNCTIONAL GROUPS-ane -ene -yne

AromaticBenzene Ring:

Arene6 carbon ring w/ alt. dbl. bonds

Alcohol Ether Amine

CARBONYL; C=OAldehyde Ester Amide

ending:

ending:

-ol ether -amine

-al -oate -amide

..R CH2 O H.. R CH2 O CH2 R

..

..R CH2 N

..

R C H

O. .. .

R C C O C R

O

..

... .. .

R C C NH2

..O. .. .

Ketone Carboxcylic Acid

ending: -one -oic acid

R CH2 C CH2 R

O. .. .R C C OH

..

..

O. .. .

RINGS

single bonds

Name: cyclo-parent cyclopentane

Multiple bonds

cyclopentene cyclopentyne

FUNCTIONAL GROUP SERIES

- OH

- O -

H - C = O

C = O

- COOH

- COO -

Ethers

Esters

Ketones

Carboxcyclic Acids

Alcohols

Aldehydes

Identify functional group present in each molecule displayed

1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde

B OC C C

C OC C O C

A H H H C C = O H

1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde

E OC C C OH

F OC C C H

D CH3 CH CH3

OH

1: Carboxcyclic Acid 2: Ester 3: Alcohol 4: Carbonyl - Ketone 5: Carbonyl - Aldehyde

G OCH3 C CH2 CH3

H OC C C O C OH

FTIR -- InfraRed

IR1. Bet vis & microwave2. Organic chemists use 4000 - 400 cm-1

3. cm-1 E of vibration

No 2 cmpds give exact sample IR (enantimoers)

2 types of molecular vibration stretching bending

3 vibrations

symmetrical asymmetrical scrissoring

Stretching Frequencies ()C-C C-O C-N 1300 - 1500 cm-1

C=C C=O C=N N=O 1900 - 1500C C C N 2300 - 2000C-H O-H N-H 3800 - 2700

2 imprt areas for prelim exam of spectra 4000 - 1300 900 - 650 1300 - 900 fct group region fingerprint complex

Imprt for -OH NH C=Ostrong bands 1600 - 1310 aromatics (benzene ring) 900 - 650 strong out-of-plane bending & ring bending

C - H Stretch

Alkanes 3000 - 2840(s)

other: near 1375 & 1450Cycloalkanes 3100 - 2990(m)

other: near 1450(m)

Alkenes above 3000(s)

other: near 1416(m); 1000-650(w); near 850(s)

Alkynes 3333 - 3267(n,s) stronger-narrower than OH & NH other: 700-610(b,s); 1370-1220(w,o)

Aromatics 3100 - 3000 & 2000 - 1650(w,o)

other: 900-675(s); 1300-1000(m)

Aldehydes 2830 - 2695(2:s) w/ near 1390 other: near 2720(m)

C to C

Alkanes below 500; 1200 - 800(w) are of little value best is C-H CH3 2962 & 2872 CH2 near 2926 & near 2853 (+/-10) CH near 1375 & near 1450

Alkenes 1667 - 1640(m)

Alkynes 2260 - 2100(w)

ALCOHOLS -- PHENOLS

Alkenes - Phenols -OH & C-O OH 3650 - 3584(b,s); 1420 - 1330(m)

CO 1260 - 1000(s)

Ethers C-O-C similar to C-C-C but more intense 1150 - 1085(s)

ETHERS

Ethers C-O-C similar to C-C-C but more intense 1150 - 1085(s)

CARBONYL C=O containing

Carbonyls (ketones, aldehydes, carboxylic acids, esters, anhydrides, amides) C=O 1870 - 1540(s)

Ketones 1300 - 1100(m)

Aldehydes 1740 - 1720 C-H 2830-2695(2:m) & near 2720(m)

Carboxylic Acids O-H 3300 - 2500(b,s)

C=O near 1766(s)

C-O & O-H near 1320-1210(m) & near 1440-1395(m)

Esters C=O 1750 - 1715(s) higher freq than ketones C-O 1210- 1163(2:s)

NITROGEN CONTAINING

Amides NH2 or NH 1650 - 1515 other: near 3520(m) & near 3400(m)

C=O 1694 & 1650(s)

C-N near 1400(m)

Amine NH near 3500(w) & near 3400(w)

other: NH 1650-1580(m)

C-N 1250 - 1020(m)

aromatic C-N 1342-1266(s)

Nitriles CN 2260 - 2222(m)

SUMMARY

Alkanes, alkyl groups C-H 2850 – 2960 m – s

Alkenes =C-H 3020 – 3100 m C=C 1640 – 1680 m

Alkynes C-H 3300 s -CC- 2100 – 2260 m

Alcohols O-H 3400 – 3650 s,b C-O 1050 – 1150 s

Aromatics =C-H 3030 m ring 1600, 1500 s

Amines N-H 3300 – 3500 m C-N 1030, 1230 m

Carbonyl Cmpds C=O 1680 – 1750 s,bCarboxylic Acids O-H 2500 – 3100 s,bNitriles CN 2210 – 2260 mNitro NO2 1540 s

N-H

O-H

C-H

CN

CC

C=O

C=N

C=C

Fingerprint

Region

4000 3000 2000 1600 1200 1000 800 600

(cm-1)

% T

rans

mitt

ance

ALKENE

4000 3000 2000 1600 1200 1000 800 600

(cm-1)

% T

rans

mitt

ance

ALKYNE

4000 3000 2000 1600 1200 1000 800 600

(cm-1)

% T

rans

mitt

ance

ALCOHOL

Website for spectral information of molecules

http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng