Online Homework for Exam 3
I . (8 points each; 24 total points) Give the IUPAC name for the following compounds.
H OH
A.
B.
C C C
H
H
HO
HO
HO
C.
N
H
H
H
OH
OH
1-Name of A: A. 3,4-octadiene B. 4,5-octadiene C. 3,5-octadiene D. 1-ethyl-3-propyldiene E. 1-propyl3-ethyldiene
2-Name of B: A. hexylamine B. cyclohexylamine C. pyridine D. cyclohexenamine E.
nitrogencyclothing
3-Name of B: A. sucrose B. -glucose C. -galactose D. -glucose E. sugar
II. (5 points each; 50 total points) As indicated by the boxes, provide the reagents, starting materials or
major product(s) of the following reaction. Show stereochemistry/regiochemistry where appropriate.
OH OH
OH OH
NaBH4
HO
4-A.HHO
H
H
OH
OH
OH OH
H
H
OH
OH
H
A.
H OH
H
HO
H
H
H
B.
OH OH
H OH
H
HO
HH
H
HO
CH3OH
OH OH
H
OH
H
H
H
H
H
D.
OH OH
H OH
H
HO
H
OH
OH
H
HO
HO
C. H
OH
H
E.
H OH
H
HO
OH
CH 2OH
OH
H
H
OH
CH 2OH
H
H
OH
OH
OH
F.
O
O
CH 3 O
5-B. A.
B.
C.
D
heat
+
O
O
O
E.
F.
6-C.
G.
H
I.
O
O
O
O
1. EtNH2
Cl
CH 3 O
Cl
2. LAH, THF
NHEt
NHEt
A.
O
B.
C.
NHEt
D.
1
AlH
E.
Online Homework for Exam 3
2
Online Homework for Exam 3
III. (20 points) Give the mechanisms and label the thermodynamic and kinetic products for the following
reaction (use electron flow arrows). Explain your choice for both products.
Br
Br
H-Br
1 eq
A.
B.
C.
Br
D.
E.
B.
C. Br
E.
F.
Br
D.
F.
16-Which intermediate(s) should be drawn?__
Br
Br
A. Br
17-Which is the thermodynamic product?__
18-Which is the kinetic product?__
IV. A. (12 points) (i) Circle the more stable structure of D-glucose. (ii) Give the mechanism for the
interconversion of the two forms of D-glucose (use electron flow arrows). (iii) Explain why acid
enhances the reaction rate.
OH
HO
HO
OH
H+
O
H2O
OH
O
HO
HO
OH
A.
19-Which is more stable?___
B.
OH
OH
O
HO
HO
OH
H2O
OH
HO
HO
O
HO
HO
OH
OH
OH
OH
B.
OH 2+
OH
O
HO
HO
OH
O H
A.
OH
OH
C.
HO
HO
OH 2+
O
HO
HO
OH
D.
O
OH
OH
E.
F.
20-Which structure(s) could be drawn for the conversion mechanism(s)?___
B. (5 points) Explain why the isomerization of -OH is much slower for t-butylcyclohexanol than for
glucose.
H+
OH
H
H
OH
H
H
H
OH2
O
A.
B.
C.
OH
D.
21-Which structure(s) should be drawn for the conversion mechanism(s)?____
3
O
E.
H
Online Homework for Exam 3
V. (10 total points) Draw a typical phospholipid. Draw the structure it spontaneously forms in water
(you can use the simple depiction of a phospholipid as I did in class). Indicate where glucose and a
steroid would be positioned if they were in water when the structure formed.
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
_
A.
B.
_
C.
D
E
22-Which structure best represents a phospholipid?____
HOH
HO
H
H
_
HOH
H
OH
OH
HOH
_
_
HO
HO
HO
H
H
HO
HO
HO
H
OH
OH
_
HO
HO
H
H
H
OH
OH
HOH
HO
HO
HO
H
H
A.
B.
C.
H
OH
OH
D
23-Which structure best represents the position of the compounds in a phospholipid?____
VI. (8 points) (i) The circles represent the core and surface of a protein. Place were you expect to find the
following amino acid side chains for a protein that folded in water.
O
O
NH3+
O-
ONH3+
O
O
NH3+
-
O
-
core
surface
core
surface
core
O
surface
core
surface
NH3+
A.
B.
C.
24-Which structure best represents the position of the side chains in a protein?____
4
D
Online Homework for Exam 3
VII. (7 total points) (i) Draw the H-bonds (straight lines) that hold these two peptides together. What is
the name of this secondary structure?
R
N
H
H
N
O
R
N
H
O
O
N
H
R
H
N
R
O
R
H
N
O
R
N
H
N
H
R
H
N
O
R
O
H
N
O
N
H
R
H
N
O
O
R
A.
R
N
H
R
R
O
O
H
N
O
R
N
H
O
N
H
R
H
N
O
R
O
H
N
O
R
N
H
R
B.
O
O
N
H
R
H
N
R
O
R
H
N
O
R
N
H
O
R
H
N
O
O
R
C.
25-Which is the best structure?____
26-What is the structure’s name A. -sheet B. anti parallel -sheet C. -helix D. parallel -sheet?___
(ii) (7 points) For which side chain, would the secondary structure be more stable: H-atom (glycine) or
isobutyl group (leucine) in water (circle one). Explain your answer.
O
N
H
H
N
O
O
N
H
H
N
O
27-The more stable would be A. glycine or B. leucine?___
28-What term(s) should you use in your discussion A. grease B. H-bond C. hydrophilic or D.
hydrophobic?____
5
Online Homework for Exam 3
VIII. (16 points) Each pair of molecules interact differently when placed in water. Show, label, and
explain the interactions and structures that form between the molecules (if any) and between the
molecules and water.
CH 3NH 3+
(i)
H
O
H
CH 3CO 2- H
O
-
H
+
O2CCH 3 CH 3NH 3
A.
CH 3NH 3+
B.
-
O2CCH 3
C.
29-Which arrangement is most likely?___
CO 2-
NH 3+
(ii)
A.
NH 3+
H
O
-
NH 3+ O2C
O2C
B.
C.
CO 2-
+
H
O
H
H
-
H3N
O2C
-
NH 3+
O2C
D.
30-Which arrangement is most likely?___
E.
NH 3+
(iii)
CO 2-
A.
NH 3+
H
O
H
O
H
B.
-
H -O2C
O2C
CO 2NH 3+
NH 3+
C.
D.
+
CO 2-
H3N
NH 3+
-
31-Which arrangement is most likely?___
6
O2C
E.
NH 3+
Online Homework for Exam 3
IX. As indicated by the boxes, provide the reagents, starting materials or major product(s) of the
following reaction. Show stereochemistry/regiochemistry where appropriate.
X. ( 35 points) (i) Give the major product formed in each reaction and the mechanisms for their formation.
(ii) Circle the aromatic ring that is more reactive for electrophilic addition, and explain your choice.
(iii) Explain the regiocontrol for addition (ortho, meta, or para), showing key resonance structures.
Make sure to explain why the other isomers are minor products.
7
Online Homework for Exam 3
36-Which structure is the key resonance structure _______?
37-Which structure(s) is the major product _______?
:
CH 3
O
O
:
O
CH 3
O:
CH 3
O
O
O
CH 3
O
:
HNO3
NO 2
NO 2
A.
B.
C.
38-Which structure is a key resonance structure _______?
O
O
CH 3
O
CH 3
O
O
O2N
NO 2
O
CH 3
O
O2N
H2SO4
CH 3
O
O
CH 3
O
NO 2
A.
B.
C.
39-Which structure(s) is the major product _______?
8
NO 2
NO 2
D.
E.
Online Homework for Exam 3
9
:
40- Which molecule is more reactive for electrophilic addition? A.
O
CH 3
O:
:
O
:
O
B.