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- 1. Draw the structure of cis-CH3CH=CHCH2CH3 showing the pi bond with its proper geometry. 2. Draw the trans isomer, and circle the coplanar atoms. Are there still six?
문제 1
문제 1a
If a hydrocarbon has nine carbon atoms, three double bonds, and one ring, how many hydrogen atoms must it have?
Hint: If you prefer to use a formula, elements of unsaturation = 1/2(2C + 2 - H)
C = number of carbons
H = number of hydrogens
문제 1b
Calculate the number of elements of unsaturation implied by the molecular formula C6H12.
Hint: If you prefer to use a formula, elements of unsaturation = 1/2(2C + 2 - H)
C = number of carbons
H = number of hydrogens
문제 1c
Give five examples of structures with this formula (C6H12). At least one should contain a ring, and at least one should contain a double bond.
Hint: If you prefer to use a formula, elements of unsaturation = 1/2(2C + 2 - H)
C = number of carbons
H = number of hydrogens
문제 2
Determine the number of elements of unsaturation in the molecular formula C4H6. Give all nine possible structures having this formula. Remember that
a double bond = one element of unsaturation
a ring = one element of unsaturation
a triple bond = two elements of unsaturation
문제 3a
Draw five more compounds of formula C4H6NOCl.
문제 4a,b,c
For each of the following molecular formulas, determine the number of elements of unsaturation, and draw three examples.
a. C4H4Cl2
b. C4H8O
c. C6H8O2
문제 4d,e
For each of the following molecular formulas, determine the number of elements of unsaturation, and draw three examples.
d. C5H5NO2
e. C6H3NClBr
문제 5a,b
Give the systematic (IUPAC) names of the following alkenes.
(a)
(b)
문제 5d,e
Give the systematic (IUPAC) names of the following alkenes.
(d)
(e)
문제 5f,g
Give the systematic (IUPAC) names of the following alkenes.
(f)
(g)
문제 6a,b
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
a. hex-3-ene
b.buta-1,3-diene
문제 6c,d
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
c. hexa-2,4-diene
d. 3-methylpent-2-ene
문제 6e,f
1. Determine which of the following compounds show cis-trans isomerism.
2. Draw and name the cis and trans (or Z and E) isomers of those that do.
e. 2,3-dimethylpent-2-ene
f. 3,4-dibromocyclopentene
문제 7a,b
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
a. cis-dimethylpent-2-ene
b. 3-vinylhex-4-ene
문제 7-25b
For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.
b. 1-bromo-1-methylcyclohexane + triethylamine(Et3N:)
문제 7c,d
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
c. 2-methylcyclopentene
d. 6-chlorocyclohexadiene
문제 7e
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
e. 2,5-dimethylcyclohexene
문제 8a,b
Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
a. 3-bromo-2-chloropent-2-ene
b. 3-ethylhexa-2,4-diene
문제 8c,d
Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
c. 3-bromo-2-methylhex-3-ene
d. penta-1,3-diene
문제 8e,f
Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
e. 3-ethyl-5-methyloct-3-ene
f. 3,7-dichloroocta-2,5-diene
문제 8g,h
Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
(g)
(h)
문제 8i
Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
(i)
문제 9a
How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.
문제 9b
Draw the six stereoisomers of octa-2,4,6-triene. Explain why there are only six stereoisomers, rather than the eight we might expect for a compound with three stereogenic double bonds.
문제 10a
Teflon-coated frying pans routinely endure temperatures that would cause polyethylene or polypropylene to oxidize and decompose. Decomposition of polyethylene is initiated by free-radical abstraction of a hydrogen atom by O2. Bond-dissociation energies of C—H bonds are about 400 kJ/mol, and C—F bonds are about 460 kJ/mol. The BDE of the H—OO bond is about 192 kJ/mol, and the F—OO bond is about 63 kJ/mol. Show why Teflon (Figure 7-5) is much more resistant to oxidation than polyethylene is.
문제 11a
For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?
a. cis-1,2-dichloroethene or cis-1,2-dibromoethene
문제 11b
For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?
b. cis- or trans-2,3-dichlorobut-2-ene
문제 11c
For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?
c. cyclohexene or 1,2-dichlorocyclohexene
문제 12
Use the data in Table 7-2 to predict the energy difference between 2,3-dimethylbut-1-ene and 2,3-dimethylbut-2-ene. Which of these double-bond isomers is more stable?
