Answers

JASPERSE CHEM 350 FINAL EXAM VERSION 1

150 points total

1. Provide names or structures for the following. 2 points each. Specify stereochemistry when
appropriate!
Note: Version 1 is relatively
trans-4-methyl-1- representative in terms of length.
Cl CH3 chlorocyclohexane Version 2 is longer than the real test
will be. But provides lots more
or trans-4-chloro-1- practice.
methylcyclohexane

Br
(R)-2-bromobutane

m-isopropylphenol

Cl

Z-2-chloro-2-hexene

HO
m-butylphenol
or meta-butylphenol
or 2-butylphenol

2. Identify the functional groups in the following molecule. (4 points)

O

OCH3

1
3. Predict the major products for the following reactions. Pay careful attention when orientation
is a factor. Draw just one major product in each case. (3 points each)

CN
+
CN
OCH3

Br2 , hv

NaOCH3
Br

1. O3

2. Me2S

HBr

OsO4, H2O2

O 1. Br2, FeBr3
2. Zn(Hg), HCl

3. Br2, hv

1. H2O, Hg(OAc)2

2. NaBH4

2
4. Classify the pairs of molecules as totally different, identical, structural isomers,
diastereomers, or enantiomers. (2 points each)

Br

Br Br Br

Br

Br Br Br

Cl CH3 Cl H

Br H Br CH3

5. Classify each chiral carbon as R or S. (2 points each)

HO H

H
CH3

6. Classify the hybridization and bond angles (109, 120, or 180) at the labelled atoms. (5 points)
O
4
2 OH
1 3

C-1 C-2 C-3 O-4

3
7. Draw the mechanisms for the following reactions. For any radical reactions, draw
propagation steps only. 5 points each.

OCH3 OCH3
Cl2

AlCl3
Cl Draw the resonance structures for the cation intermediate.

H H H Br
Br2 , hv
Ph Ph

Br2 , H 2 O Br

OH

4
8. Draw the products of the following multi-step sequences. (4 points each)

Me Br 1. NaOH

2. HBr, peroxides
Ph 3. NaOMe

CH3 1. SO3, H2SO4

2. 2-bromopropane, AlCl3

3. H2O, H+

OH 1. H2SO4
2. HBr, Peroxides

3. NEt3

9. Draw as many structural isomers as you can for C6H14. Circle any that are chiral. (Note: be
careful! You will lose points for any repeats!) (6 points)

None are chiral

5
T
e 10. Rank the Following, from most to least. 2 points each.
Cl
x a. Reactivity toward S N2 Br
t

I Cl
T T
e e
x •
b. Stability x
• • t •
t

CH3 H
c. Stability H CH3
H
Me2CH H
CH3 1. Equatorial preferred
H Me2CH Me2CH 2. If forces to be axial,
H
worse for big group than for
smaller group

d. Acidity PhCO2 H (CH3 )2 NH HCl CH3 CH2 OH 1. Anion stability

2. HCl by memory is
strong
3. Electronegativity factor
4. Resonance factor
Me HMe Me Me
H H Me H Me
e. Stability 1. staggered vs eclipsed
H H H H
H H H 2. Anti > gauche
Me H H
H HH
Me 3. Eclipsed > total eclipsed

OH OH OH
f. Reactivity toward
H2 SO4 /Î catalyzed Cation stability is key
dehydration

OH
g. Boiling Point
OH

1. Hydrogen bonding
2. Molecular weight factor
6
11. Provide reagents for the following transformations. You may use anything you like. Each
can be done within ≤3 steps. (4 points each)

Br
OH T
e
x Br
t

H2N Br

12. Provide the appropriate reactant for the following transformation. (3 points)

H OH
CH3 CO3 H, H 2 O

HO H

7
13. Suggest a structure for X, given the following info: (5 points)

• Formula: C8H12O
• It Reacts With excess H2/Pt to produce C8H16O
• When it reacts with O3/Me2S, one of the products is CH2=O.

14. Which of the following are aromatic

H
N

15. Draw the products and mechanism for the following reaction:

1 H-Br

16. Rank the following:

O Combined
O O
Diels-Alder
+ O Reactivity
+ + O
O
O

Br Cl Br Combined
+ + O + O SN2
Reactivity
ONa ONa ONa