Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.55P
For each compound drawn below:
a. Label each
b. Classify each conformation as cis or trans.
c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.
d. Draw the second possible chair condformation for each compound.
[1] 
[b] 
[c] 
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Students have asked these similar questions
5.
Use the MS data to answer the questions on the next page.
14.0
1.4
15.0
8.1
100-
MS-IW-5644
26.0
2.8
27.0
6.7
28.0
1.8
29.0
80
4.4
38.0
1.0
39.0
1.5
41.0
1.2
42.0
11.2
43.0
100.0
44.0
4.3
79.0
1.9
80.0
2.6
Relative Intensity
40
81.0
1.9
82.0
2.5
93.0
8.7
20-
95.0
8.2
121.0
2.0
123.0
2.0
136.0
11.8
0
138.0
11.5
20
40
8.
60
a.
Br
- 0
80
100
120
140
160
180
200
220
m/z
Identify the m/z of the base peak and molecular ion.
2
b.
Draw structures for each of the following fragments (include electrons and charges): 43.0, 93.0,
95.0, 136.0, and 138.0 m/z.
C.
Draw a reasonable a-fragmentation mechanism for the fragmentation of the molecular ion to
fragment 43.0 m/z. Be sure to include all electrons and formal charges.
6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium
ion (CsH6N) and show your work.
None
Stereochemistry: Three possible answers- diastereomers, enantiomers
OH
CH₂OH
I
-c=0
21108 1101
41745 HOR
CH₂OH
IL
Но
CH₂OH
TIL
a. Compounds I and III have this relationship with each other: enantiomers
b. Compounds II and IV have this relationship with each other:
c. Compounds I and II have this relationship with each other:
d. *Draw one structure that is a stereoisomer of II, but neither a
diastereomer nor an enantiomer. (more than one correct answer)
Chapter 4 Solutions
Organic Chemistry-Package(Custom)
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - (a) Classify the carbon atoms in each compound as...Ch. 4 - Problem 3.3 Classify a carbon atom by the number...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Give the IUPAC name for each compound. a. c. b. ...Ch. 4 - Give the IUPAC name for each compound. a....
Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.12PCh. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.17PCh. 4 - a.Draw the three staggered and three eclipsed...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Prob. 4.23PCh. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.26PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.29PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.32PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.35PCh. 4 - 3.31 For each alkane: (a) classify each carbon...Ch. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Give the IUPAC name for each compound. a. h.k....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - Considering rotation around the bond highlighted...Ch. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - Prob. 4.52PCh. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Which of the following compounds are lipids?Ch. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.74PCh. 4 - Prob. 4.75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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