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Reactions that Generate Aldehydes & Ketones

Consider the possible formation of an aldehyde or ketone product when each of the ten compounds in the column on the left is treated with each of the reagents shown in the top row. Check the designated answer box if you believe an aldehyde or ketone will be formed.
Assume that the reagents may be present in excess. For each checked reaction, try to draw the structure of the major product(s).

Starting
Material		 Reagents
PCC
C5H5NHCrO3Cl		 Jones' Reagent
CrO3 in aq. acid		 Pb(OAc)4
[ or HIO4 ]		 (i) O3
(ii) Zn dust		 H3O+ &
HgSO4 		(i) BH3 in THF
(ii) H2O2 + NaOH
Structure of cyclohexanol, a cyclohexane ring bearing one hydroxyl group
Structure of 2,5-dimethyl-3-hexyne, an internal alkyne flanked by two isopropyl groups
Structure of benzyl alcohol, a benzene ring bearing a CH2OH group
Structure of benzene, a six-membered aromatic ring
Structure of 5-methyl-4-hexen-2-ol, a trisubstituted allylic secondary alcohol
Structure of tert-butanol (2-methyl-2-propanol), a tertiary alcohol
Structure of 2,3-dimethyl-2-butene, a tetrasubstituted alkene
Structure of 1-methylcyclopentene, a cyclopentene ring with a methyl on the double bond

Structure of 1,3-propanediol, HOCH2CH2CH2OH
Structure of 2-methyl-2,3-pentanediol, a vicinal diol with adjacent tertiary and secondary OH groups


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