1. Which statements are true about constitutional isomers?
a. They have the same molecular formula.
b. They have the same molecular weight
c. They have the same order of attachment of atoms
d. They have the same physical properties.
2. Explain the meaning of the designations D and L as used to specify the configuration of
carbohydrates.
The D and L are used to describe the position of the OH group on the penultimate carbon. If
the OH is on the left, then it is an L-sugar. If on the right then it is a D-sugar
3. Reducing agents normally contain what element?
Hydrogen
4. What are the two requirements for organic compounds to aromatic?
Containing a magic number of pi electrons defined by the equation 4n+2
and moving the pi electrons in a circular direction using resonance forms
5. All organic acid derivatives can be hydrolyzed to what type of an organic compound?
Carboxylic acids
6. Do all enantiomers have a non-superimposable mirror image?
Yes
7. What is the requirement for a sugar to be a non-reducing sugar?
Must be an acetal
8. Below is a Fisher structure for glucose. Beside it draw a Fischer structure of the C-4 epimer of
glucose.
9. Other than hydrogen and carbon, what other element is common to all amines?
Nitrogen
10. Give two reasons for the chair conformation of cyclohexane being more stable than the boat
conformation.
Bond angles are 109.5° and no eclipsing of hydrogen atoms
11. Give an acceptable name for the following. Be sure to include stereochemistry when applicable.
R-1-bromopropan-1-ol
R-2-bromo-2methylbutanoic acid
R-2-bromo-2-methylbutanamide
Cis-hex-5-yn-2-ene
2-cyclohexenone
Trans-5-cyclodecenol
4--tbutylheptane
Trans-3-oxo-4-hexenal
Trans-4-phenylpropen-1-ol
Methanoic anhydride
2-aminobutanoic acid
Cis,cis-2,4-hexdiene
benzophenone
2-methylnaphthalene
3-hydroxy-2-methyl-5-cyclohexenone
Cyclohexane carboxylic acid
(2R,3S)-2,3,4-trihydroxybutanal
12.
Cyclohexane carbaldehyde
13. Give mechanisms for the following transformations.
a.
b
.
c.
14. Label the following as reducing or non-reducing sugars.
H OH
H OH
H OH
a. HO
HO
HO
HO
O
HO
H
H HO
H
H HO
H
b.
HO
HO
HO
OH
H
H HO
Lactose
reducing
OH
CH 2OH
OH O
c.
OH
d. HO
HO
CH 2OH
methyl-D-ribofuranoside
nonreducing
CH 2OH
Sucrose nonreducing
H OH
OCH 3
O
CH 2OH
OH O
HO
O CH 3
H
H HO
methyl-D-glucopyranoside
nonreducing
15. Starting from cyclohexanone and any other reagents, give a synthesis for the following organic
molecules.
a.
b.
c.
d.
16. Give major products for the following