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Relative Acid Strength I

Problem A B C D Which is the
strongest acid 		Which is the
weakest acid
1
Tetrahydropyran, a six-membered cyclic ether (oxane)
Cyclopentanecarboxylic acid
Cyclohexanone
Cyclopentylmethanol, a primary alcohol
A
B
C
D
A
B
C
D
2
Phenol, benzene ring bearing an OH group
Anisole, benzene ring bearing a methoxy (OCH3) group
Cyclohexanol
4-Nitrophenol, phenol with a nitro group para to OH
A
B
C
D
A
B
C
D
3
Succinimide, a five-membered cyclic imide with an N-H
Piperidine, a six-membered amine ring with an N-H
2-Piperidinone (delta-valerolactam), a six-membered cyclic amide
1-Methylpyrrolidine, a five-membered amine with N-methyl, no N-H
A
B
C
D
A
B
C
D
4
Cyclopentylacetic acid
2-Chloro-2-cyclopentylacetic acid, single Cl on the alpha carbon
Cyclopentylacetic acid with two chlorines on the ring carbon next to the alpha carbon
2,2-Dichloro-2-cyclopentylacetic acid, two Cl on the alpha carbon
A
B
C
D
A
B
C
D

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