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Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure문제 45
Draw 1,2,3,4,5,6-hexachlorocyclohexane with
a. all the chloro groups in axial positions.
b. all the chloro groups in equatorial positions.
문제 46
Using the data in Table 3.9, calculate the percentage of molecules of cyclohexanol that have the OH group in an equatorial position at 25 °C.
문제 47
The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C1−C2 bond?
문제 48a,b,c
Is each of the following a cis isomer or a trans isomer?
a,
b.
c.
문제 48d,e,f
Is each of the following a cis isomer or a trans isomer?
d.
e.
f.
문제 49
Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxialsubstituted conformer: trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?
문제 50a
Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane.
문제 50c
Which compound is more stable: cis-1-ethyl-2-methylcyclohexane or trans-1-ethyl-2-methylcyclohexane?
문제 51a,b
For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:
a. cis-1,2-
b. trans-1,2-
문제 51c,d
For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:
c. cis-1,3-
d. trans-1,3-
문제 51e,f
For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:
e. cis-1,4-
f. trans-1,4-
문제 53
a. Draw Newman projections of the two conformers of trans-1,3-dimethylcyclohexane.
b. Which of the conformers predominates at equilibrium?
문제 54a
Calculate the energy difference between the two chair conformers of trans-1,4-dimethylcyclohexane.
문제 54b
What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?
문제 55a
Draw a condensed structure and a skeletal structure for each of the following:
a. sec-butyl tert-butyl ether
문제 55a,b
Draw a condensed structure and a skeletal structure for each of the following:
a. sec-butyl tert-butyl ether
b. isoheptyl alcohol
문제 55c,d
Draw a condensed structure and a skeletal structure for each of the following:
c. sec-butylamine
d. isopentyl bromide
문제 55g
Draw a condensed structure and a skeletal structure for each of the following:
g. 4-(1,1-dimethylethyl)heptane
문제 55h
Draw a condensed structure and a skeletal structure for each of the following:
h. 5,5-dibromo-2-methyloctane
문제 55i
Draw a condensed structure and a skeletal structure for each of the following:
i. 3-ethoxy-2-methylhexane
문제 55k
Draw a condensed structure and a skeletal structure for each of the following:
k. 3,4-dimethyloctane
문제 55l
Draw a condensed structure and a skeletal structure for each of the following:
l. 5-isopropyldecane
문제 57(7,8)
a. What is each compound’s systematic name?
b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.
7.
8. CH3OCH2CH2CH2OCH3
문제 57(3,4)
a. What is each compound’s systematic name?
b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.
3.
4. (CH3CH2)4C
문제 57(1,2)
a. What is each compound’s systematic name?
b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.
1. (CH3)3CCH2CH2CH2CH(CH3)2
2.
문제 57(5,6)
a. What is each compound’s systematic name?
b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.
5. BrCH2CH2CH2CH2CH2NHCH2CH3
6.
문제 58
Which of the following represents a cis isomer?
문제 59(1)
a. How many primary carbons does each of the following compounds have?
b. How many secondary carbons does each one have?
c. How many tertiary carbons does each one have?
1.
문제 59(2)
a. How many primary carbons does each of the following compounds have?
b. How many secondary carbons does each one have?
c. How many tertiary carbons does each one have?
2.
문제 60
Which of the following conformers of isobutyl chloride is the most stable?
