Worksheet No.

8
Aldehydes and Ketones: Structure and Reactions

I. Draw the structures or give the systematic name the following.

O O

1. CH3CHCH2CCHCH3 2. CH3CHCH2CH

Cl CH2CH3 HC

CH2

O
4. 5.
CH
OH
C

ANSWERS:

1. 5-chloro-2-ethyl-3-hexanal
2. 3-methylpent-4-en-1-al
3. 5-Ethyl-4-methylcyclopent-2-ene carbaldehyde
4. 4-hydroxy-5-methyl-2-phenylhexan-1-al
5. 1-cyclopropylpropan-1-one

6. Bromoacetone

7. (S)-2-Hydroxypropanal
8. 2-Methyl-3-heptanone

9. (2S,3R)-2,3,4-Trihydroxybutanal

10. 2,2,4,4-Tetramethyl-3-pentanone

II. Write the structural formulas of the product(s) formed when

A. propanal B. acetophenone reacts with the following reagents.

propanal acetophenone

1. NaBH4 in Methanol
 no reaction
32 2. Ag(NH ) +

3. C6H5MgBr, then
H3O+

4. H2 in Pt

5. Hydroxylamine

6. Phenlhydrazine

7. LiAlH4 then water

8. HCN
 9. Diethylamine

10. 2 CH3OH, HCl

catalyst
 III. Show how benzaldehyde could be synthesized from Benzyl alcohol.

Pyridinium chlorochromate (PCC) is a reagent known for its mild oxidation properties. When
it's used to oxidize a primary alcohol, it selectively converts it into an aldehyde. This
selectivity arises from the reaction mechanism, where PCC facilitates the oxidation process
without overoxidizing the aldehyde to a carboxylic acid. This makes PCC particularly useful
in organic synthesis when the desired product is an aldehyde rather than a carboxylic acid.
Additionally, PCC is often dissolved in solvents like dichloromethane (CH2Cl2) to facilitate
the reaction and improve its efficiency. The combination of PCC's selectivity and its
compatibility with organic solvents makes it a valuable tool in synthetic chemistry.