Isomers of C5H12O by Dr.Gergens

Draw all fourteen isomers of C5H12O Goals: draw all isomers & identify functional groups; alcohols (eight) & ethers (six) identify methyl, primary, secondary & tertiary carbon centers define a heteroatom and give examples identify alcohol type as primary, secondary & tertiary alcohols identify, name & draw branch names for methyl ethyl n-propyl isopropyl n-butyl sec-butyl iso-butyl t-butyl • amyl isoamyl sec-amyl • sec-isoamyl • neopentyl • tert-amyl • give abbreviations for branch names Me, Et, nPr, iPr, nBu, sec-Bu, iBu, t-Bu give common and IUPAC to ethers and alcohols identify chiral centers identify planes of symmetry

The fourteen isomers of C5H12O - alcohols (eight)

The fourteen isomers of C5H12O - ethers (six)

The fourteen isomers of C5H12O - carbon centers a CH3 bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon C 1° a carbon bonded to only one carbon is 1° primary C 2° a carbon bound to two carbons is 2° secondary 3° C a carbon bound to three carbons is 3° tertiary

The fourteen isomers of C5H12O - ethers (six) 1° primary carbons

The fourteen isomers of C5H12O - ethers (six) 2° secondary carbons

The fourteen isomers of C5H12O - ethers (six) 3° tertiary carbons

The fourteen isomers of C5H12O - alcohols (eight) 1° primary carbons

The fourteen isomers of C5H12O - alcohols (eight) 3° tertiary carbons

The fourteen isomers of C5H12O - alcohols (eight) 4° quaternary

The fourteen isomers of C5H12O - heteroatom centers a CH3 methyl group bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon CH3 N O F Me C 1° NH2 C 1° OH C 1° F a heteroatom bonded to a 1° primary center is considered primary 2° C N H a nitrogen heteroatom bonded to two carbons as a secondary amine 3° C N a nitrogen heteroatom bonded to three carbons as a 3° tertiary amine

The fourteen isomers of C5H12O - heteroatom centers a CH3 bonded to a heteroatom is a methyl group a heteroatom is an atom other than carbon CH3 N O F Me C 1° OH a hydroxyl bonded to a primary carbon center is a 1° alcohol 2° C OH a hydroxyl bonded to secondary carbon center is a 2° alcohol 3° C OH a hydroxyl bonded to tertiary carbon center is a 3° alcohol

The fourteen isomers of C5H12O - 1°, 2° & 3° alcohols

The fourteen isomers of C5H12O - ethers (six) - branch names methyl C methyl C methyl C methyl C

The fourteen isomers of C5H12O - ethers (six) - branch names ethyl C ethyl

The fourteen isomers of C5H12O - ethers (six) - branch names isopropyl C C 2° C C n-propyl 1°

The fourteen isomers of C5H12O - ethers (six) - branch names sec-butyl C 2° n-butyl C 1°

The fourteen isomers of C5H12O - ethers (six) - branch names 3° C t-butyl isobutyl 3° C C C C C C 1° C 3° 1° C C

The fourteen isomers of C5H12O - branch name abbreviations t-butyl tBu isobutyl, iBu methyl, Me methyl, Me ethyl, Et sec-butyl sec-Bu isopropyl iPr methyl, Me n-propyl, nPr n-butyl nBu ethyl, Et methyl,Me

The fourteen isomers of C5H12O - additional branch names neopentyl C 3° tert-amyl or t-pentyl C 3° C 2° sec-isoamyl sec-isopentyl or isoamyl C 1° isopentyl or sec-pentyl or sec-amyl n-pentyl or n-amyl C C C 1° C C C C 2° C C C

The fourteen isomers of C5H12O - common naming of ethers t-butyl methyl ether isobutyl methyl ether sec-butyl methyl ether ethyl isopropyl ether n-butyl methyl ether ethyl n-propyl ether KNOW these branch names used in these commonly named ethers. Simple branch name are also used in naming alcohols and alkyl halides.

The fourteen isomers of C5H12O - IUPAC naming 2,2-dimethyl-1-propanol 1,1-dimethyl-1-propanol 3-methyl-2-butanol 2-methyl-1-butanol 3-methyl-1-butanol 3-pentanol 2-pentanol 1-pentanol KNOW IUPAC traditional naming rules in naming alcohols, ALWAYS 1 & 2: 1) circle the longest continuous chain & 2) start numbering to the closest hydroxyl

The fourteen isomers of C5H12O - IUPAC naming 1,1-dimethyl-1-methoxyethane 2-methyl-1-methoxypropane 2-methoxybutane 2-ethoxy-2-propane 1-methoxybutane 1-ethoxypropane KNOW IUPAC traditional naming rules, ALWAYS 1 & 2: 1) circle the longest continuous chain & 2) number to the closest branch

The fourteen isomers of C5H12O - chiral centers, asymmetric centers

The fourteen isomers of C5H12O - chiral centers, asymmetric centers

Identifying Chiral Centers by Dr.Gergens

Not chiral-molecule has a plane of symmetery Not chiral-molecule has Chiral-molecule is asymmeteric Not chiral-molecule has a plane of symmetery

Not chiral-molecule has a plane of symmetery Not chiral-molecule has Chiral-molecule is asymmeteric This carbon center is NOT chiral

Not chiral-molecule has a plane of symmetery This carbon center is NOT chiral This carbon center is NOT chiral

This carbon center is NOT chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral This carbon center is chiral

This carbon center is NOT chiral This carbon center is chiral This carbon center is chiral

This carbon center is NOT chiral This carbon center is NOT chiral

This carbon center is chiral This carbon center is chiral

This carbon center is chiral This carbon center is chiral

These carbons center are NOT chiral This carbon center is NOT chiral These carbons center are chiral This carbon center is chiral These carbons center are chiral This carbon center is chiral

The fourteen isomers of C5H12O - alcohols (eight) - branch names sec-pentyl or sec-amyl n-pentyl or n-amyl C C C 1° C C C C 2° C C C

The fourteen isomers of C5H12O - alcohols (eight) - branch names 2° sec-isoamyl sec-isopentyl or isoamyl C 1° isopentyl or

The fourteen isomers of C5H12O - alcohols (eight) - branch names neopentyl C 3° t-tert-amyl or t-pentyl C 3°

The fourteen isomers of C5H12O - alcohols (eight) - branch names neopentyl C 3° t-tert-amyl or t-pentyl C 3° C 2° sec-isoamyl sec-isopentyl or isoamyl C 1° isopentyl or sec-pentyl or sec-amyl n-pentyl or n-amyl C C C 1° C C C C 2° C C C

The fourteen isomers of C5H12O - ethers (six) - branch names t-butyl isobutyl methyl methyl ethyl sec-butyl isopropyl methyl n-propyl n-butyl ethyl methyl

The fourteen isomers of C5H12O - ethers (six) t-butyl 1° isobutyl 1° methyl 3° methyl 3° ethyl sec-butyl isopropyl 1° 1° 2° methyl 2° 2° n-propyl n-butyl ethyl 1° 1° 2° 2° 2° methyl

The fourteen isomers of C5H12O - alcohols (eight) neopentyl 1° t-tert-amyl t-pentyl 1° 3° 4° 2° 1° sec-isoamyl 1° 3° 2° 3° 2° isopentyl 1° 2° 3° 1° 2° 2° 2° sec-amyl n-pentyl 1° 2° 2° 1° 2° 2° 2° 2°