Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2 ¬ C3 bond (b) 3,3-dimethylhexane about the C3 ¬ C4 bond
Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2 ¬ C3 bond (b) 3,3-dimethylhexane about the C3 ¬ C4 bond
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter11: Alkanes
Section: Chapter Questions
Problem 11.69P: Dodecane, C12H26, is an unbranched alkane Predict the following: Will it dissolve in water? Will it...
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1. Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2 ¬ C3 bond (b) 3,3-dimethylhexane about the C3 ¬ C4 bond
2. refer to the questions below:
Transcribed Image Text:H
(e)
CH3
CH3
-CH3
Hu
CH3
H
H-
H
CH3
ČH3
H
H
H CH3
H
CH,
CH3
CH3
CH, H
CH, H
(f)
CH3
H.
CH3
H.
H
H.
CH3
H;C.
CH3
H.
CH3
CH(CH3)2
HạC
CH;CH3
H*
CH3
CH3
H3C
CH3
H
H
CH,
CH3
(g) Name the structures given in Problem 3-34, parts (a), (c), (e), and (f). Make sure your names are the same for struc-
tures that are the same, and different for structures that are different.
*3-35
(a) Draw and name the five cycloalkane structures of formula C3H10. Can any of these structures give rise to geometric
(cis-trans) isomerism? If so, show the cis and trans stereoisomers.
(b) Draw and name the eight cycloalkane structures of formula C,H12 that do not show geometric isomerism.
(c) Draw and name the four cycloalkanes of formula C,H12 that do have cis-trans isomers.
Draw the structure that corresponds with each name.
(a) 3-ethyloctane
(d) 2,3-dimethyl-4-propylnonane
(g) cis-1-ethyl-4-methylcyclohexane
(G) pentylcyclohexane
Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match
the description.
(a) an isopropylheptane
(d) a trans-dihalocyclopentane
Write structures for a homologous series of alcohols (R-OH) having from one to six carbons.
3-36
(b) 4-isopropyldecane
(e) 2,2,4,4-tetramethylhexane
(h) isobutylcyclopentane
(k) cyclobutylcyclohexane
(c) sec-butylcycloheptane
(f) trans-1,3-diethylcyclopentane
(i) tert-butylcyclohexane
(1) cis-1-bromo-3-chlorocyclohexane
3-37
(b) a diethyldecane
(e) a (2,3-dimethylpentyl)cycloalkane
(c) a cis-diethylcyclohexane
(f) a bicyclononane
3-38
3-39
Give the IUPAC names of the following alkanes.
(a) CH;C(CH3)2CH(CH2CH3)CH,CH;CH(CH;)2
(b) CН,CH, — ҫн—CH,CH, — ҫн—CH,
CH,CHCH,
CH,CHCH,
tx
(c)
(d)
CH,CH,
(e)
CH,CH,
CH,
(f)
ÇH,CH,
(g)
C(CH,CH,),
(h)
ÇH,CH,
CH,CH,CH,
CH(CH,),
3-40
Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentane along the C2-C3 bond. Place C2 in
front, represented by three bonds coming together in a Y shape, and C3 in back, represented by a circle with three bonds
pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and the ethyl
group on the back carbon. Begin your graph at the 0° dihedral angle and begin to turn the front carbon. Show the Newman
projection and the approximate energy at each 60° of rotation. Indicate which conformations are the most stable (lowest
energy) and the least stable (highest energy).
3-41
The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.
(a) 2-ethylpentane
(d) 2-dimethylbutane
(b) 3-isopropylhexane
(e) 2-cyclohexylbutane
(c) 5-chloro-4-methylhexane
(f) 2,3-diethylcyclopentane
Transcribed Image Text:(a) There are 18 isomeric alkanes of molecular formula C;H18. Draw and name any eight of them.
(b) Draw and name the six isomeric cyclopentanes of molecular formula C,H4. These will include four constitutional
isomers, of which two show geometric (cis-trans) stereoisomerism.
3-33
Which of the following structures represent the same compound? Which ones represent different compounds?
н сн,
3-34
H H H
H H H H
H CH;
CH, CH,
(a)
Н-с—с—с—н н—с—с-с-с-н н-с—с— н Н-с—с- н н—с—с—н
CH, H
нн CH,
H H HH
H CH,
нн
(b)
CH,
(c)
CH,
„CH,
CH;
"H
CH
CH, Н,
"H
CH,
H
"CH,
H
CH,
CH,
H
(d)
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