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Advanced level organic chemistry PART 14.7: Structural isomers of molecular formula C5H12O

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Doc Brown's Advanced Chemistry: Part 14.7

Structural isomers of molecular formula C5H12O

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See also Examples of the effects of isomerism on the similarity or difference in the physical and chemical properties of structural isomers

and Examples of comparing the physical and chemical properties of R/S (optical) isomers (enantiomers)

The 14 aliphatic non-cyclic alcohol and ether structural isomers of molecular formula C5H12O (Mr = 88)

This is an example of functional group isomerism (alcohol C-O-H linkage, ether C-O-C linkage)

There are eight isomeric alcohols and six isomeric ethers.

The eight alcohols

(1) pentan-1-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b (a primary alcohol)

(2) pentan-2-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

(secondary alcohol), and will exhibit optical (R/S) isomerism, the 2nd carbon atom is a chiral centre.

(3) pentan-3-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

 (secondary alcohol)

(4) 2-methylbutan-1-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

a primary alcohol that will exhibit optical (R/S) isomerism, the 2nd carbon atom is a chiral centre.

(5) 3-methylbutan-1-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

a primary alcohol

(6) 2-methylbutan-2-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

a tertiary alcohol

(7) 3-methylbutan-2-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b ,

a secondary alcohol, will exhibit optical (R/S) isomerism

(8) 2,2-dimethylpropan-1-ol isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

a primary alcohol

The six ethers

(9) 1-methoxybutane isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

(10) 2-methoxybutane, isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

this ether will exhibit optical (R/S) isomerism, 2nd carbon atom is chiral

(11) 1-ethoxypropane isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

(12) 2-ethoxypropane isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

(13) 1-methoxy-2-methylpropane isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b

(14) 2-methoxy-2-methylpropane isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b , isomers of C5H12O  structural formula alcohols and ether structure and naming (c) doc b


Associated links

Index of sets of isomers for a given molecular formula

The molecular structure and naming of aliphatic ALCOHOLS including isomeric ethers

INDEX of ALL revision notes on the chemistry of ALCOHOLS (and mention of ethers)

Isomerism: introduction, structural isomerism - chain, positional, functional group, tautomerism

Stereoisomerism: introduction, definition, priority rules, E/Z isomerism (cis/trans isomerism)

Stereoisomerism - R/S isomerism (optical isomerism) - definition - examples explained

index for all isomerism pages

Website content Dr Phil Brown 2000+. All copyrights reserved on revision notes, images, quizzes, worksheets etc. Copying of website material is NOT permitted. Exam revision summaries & references to science course specifications are unofficial.

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