Organic Chem Test 2

Which * class=”smfm-flex-item”>CH3 line n line ch3 two dots over n line down from n ch3
There are 8 isomers that have the molecular formula C5H11Br. How many of these are tertiary alkyl bromides?
1
Which of the following is sec-butyl alcohol?
CH3CH per OH close per CH2CH3
Identify the number of tertiary carbons in the following structure.
3
What is the common name for the following structure?
ch3-ch-ch3 WITH ch3 in bottom?
isobutane
Give the IUPAC name for the following structure:
4 slashs left with 3 slashes up 2 slashes on right with one down
4-Isopropyloctane
There is something wrong with the following name. Write the structure and correct the name: 2-ethylpropane.
ch3 line ch line ch3 down connect from ch line ch2 line ch3
2-methylbutane.
Give structures for the three isomers with molecular formula C5H12 and provide the common name of each.
up 4 swigs is pentane
up 3 swigs with line up is isopentane
cross is neopentane
Provide an acceptable name for the alkane shown below.

CH3CH2CH2CH2CH2CH3

hexane
Provide an acceptable name for the alkane shown below.
ch3 line ch line ch2ch2ch per ch3 closed per 2 with down connect from ch line ch2ch3
2,5-dimethylheptane
Provide an acceptable name for the alkane shown below.
ch3 up 7 swig fourth dip line down start ch3 up 3 swigs to ch3 end of main 3 lines ch3 at ends
5-sec-butyl-2,2-dimethylnonane
Provide an acceptable name for the alkane shown below.
ch3 to ch2 to ch2 to ch2 to ch2 to ch2 to ch to ch2 to ch2 to ch3 with line up from ch to ch per ch3 closed 2
4-isopropyldecane
Provide an acceptable name for the alkane shown below.
ch3 to ch2 to ch2 to ch to ch to ch2 to ch to ch2 to ch3 up connect from first ch line ch3 second ch line down ch2ch2ch3 third ch up line ch2ch3
3-ethyl-6-methyl-5-propylnonane
Provide an acceptable name for the alkane shown below.
ch3 to ch2 to ch2 line c line c line h connect first c up ch3 down ch3 second c up ch2ch3 down ch2ch3
3-ethyl-4, 4-dimethylheptane
Draw an acceptable structure for 4-t-butyloctane.
ch3 down 7 swigs end ch3 3rd dip down c per ch3 close per 3
Draw an acceptable structure for 3-ethyl-3-methylhexane
ch3 to ch2 to ch2 line to c line to ch2 to ch3 with up line from c to ch3 and line down to ch2 ch3
Draw an acceptable structure for 4-isopropyl-2-methylheptane.
ch3 to ch to ch2 to ch to ch2 to ch3 with line connect from first ch to ch3 and line down from sec ch to ch per ch3 close per 2
Draw an acceptable structure for 6-ethyl-2,6, 7-trimethyl-5-propylnonane.
ch3 up 8 swig lines to ch3 first dip line ch3 fourth dip line to two swig to left to ch 3 fifth dip v to ch3 on right and left line up to ch3 sixth dip to ch3
Provide an acceptable name for the alkane shown below.

ch3 line c line ch2ch2ch per ch3 closed per 2 line up from c c per ch3 closed per 3 line down h

2,2,3,6-tetramethylheptane
Provide an acceptable name for the alkane shown below.
ch3 ch2 ch2 ch2 line c up line h down line ch3 ch2 line c line up ch2 ch2 ch per ch3 closed per 2 line ch2 ch2 ch3
6-ethyl-2-methyl-5-propyldecane
Give the systematic name of the alkane shown below.
6 swigs three branch on right second dip line up line right fifth dip line down line right
4-ethyl-2,2,7-trimethylnonane
Give the systematic name of the alkane shown below.

6 swigs fourth dip line down with 4 swigs fifth dip line up

3-ethyl-4-isopropyloctane
Name the compound
ch3 line ch line ch line ch2 ch3 from first ch up ch2 ch3 from sec ch ch2 ch2 ch3
4-ethyl-3-methylheptane
Provide an acceptable name for the compound shown below.
up 5 swig dip 2 with down v dip four line down and right line
3,3,5-trimethylheptane
Provide an acceptable name for the compound shown below.

up 6 swig first dip a v down fourth dip down line right 2 swig

5-ethyl-3,3-dimethyloctane
Give the systematic name of the cycloalkane shown below.
hexagon with line on right to h3c right down line to h3 left bottom line ch2 ch2 ch2 ch3
4-butyl-1,2-dimethylcyclohexane
Draw an acceptable structure for sec-butylcyclopentane.
pentagon left top dip half of a octogon
Provide the systematic name of the compound shown
hexagon with 4 swig bottom half pentagon right
4-butyl-1-ethyl-2-methylcycloheptane
Give the formula
looks like a rat
c8h14
Name the compound
pentagon with right line to ch down connect to ch2 up connect c to ch2 ch up ch3 down ch2 ch2
2-cyclopentyl-4-methylhexane
Determine the number of hydrogens in limonene.
16
Provide an acceptable name for the compound shown below.
hexagone with right bottom line out and down to v shape
isobutylcycloheptane
Provide an acceptable name for the compound shown below.

cl up 7 swig line third dip v shape with br attached to each

3,3-dibromo-1-chloroheptane
Provide the common name of the compound
h3c v line to ch v line down to h3c attached to ch line ch2 ch2 ch2 ch2 cl
isoheptyl chloride
Provide the IUPAC name of the compound.
h3c v line to ch v line down to h3c attached to ch line ch2 ch2 ch2 ch2 cl
1-chloro-5-methylhexane
What is the common name for the following structure?

ch3 line c line br up line from c ch3 down line from c ch3

t-Butyl bromide
Give the IUPAC name for the following compound:
hexagone right up line ch3 right down line cl
1-chloro-2-methylcyclohexane
Which of the following is di isopropyl ether?
per CH3 close per 2CHOCH per CH3 close per 2
Draw all ethers with molecular formula C4H10O.
up 4 swigs first dip circle
down 4 swigs sec dip circle
up three swig first dip circle sec dip line down
Draw all possible constitutional isomers for C2H6O and give common names for each structure.
H to c to c to oh two dots low n high each c connect to h up n down ethyl alcohol

h to c to o with dots top n bottom to c to h with h connect to c both top n bottom dimethyl ether

Give the IUPAC name for the following structure:

hexagon with ch3 oh cl attached

5-chloro-2-methylcyclohexanol
Which of the following compounds does not have the molecular formula C6H14O?
cyclohexanol
Give the structure of isopentyl alcohol.
side v end ch3 connect to ch line to ch2 ch2 oh
Provide the systematic name of the compound shown.

up 6 swig first dip up with v fourth dip line to oh

6,7-dimethyl-3-octanol
Name the structure.

h3c line ch line ch2 ch2 ch2 ch2 cl with line down from ch to oh

6-chloro-2-hexanol
Provide an acceptable name for the compound shown below.
hexagon top line up n right bottom line down to right low line to oh
5-ethyl-2-methylcyclohexanol
Provide an acceptable name for the compound shown below.

up 4 swig third dip up line to hn up 2 swig

N-ethyl-2-pentanamine or N-ethylpentan-2-amine
Classify the following amines as primary, secondary, or tertiary
prime , sec , sec
Provide the common name of the compound.

h3c line c line ch3 connect from c up line ch3 down line n v shape h3c on right ch3 left

tert-butyldimethylamine
Provide the IUPAC name of the compound.

h3c line c line ch3 connect from c up line ch3 down line n v shape h3c on right ch3 left

N,N,2-trimethyl-2-propanamine
Provide the IUPAC name of the compound.
h2nch2ch2ch2ch2oh
4-amino-1-butanol
Draw the structure of 3-chloro-N-ethyl-2-hexanamine.
hexagon no right side line from the right ch3 n with line connect to h down to next dip line out to h3c next dip line cl then add two swig to ch3
Give the structure of tetramethylammonium chloride.
ch3 line n line ch3cl from n line up ch3 line down ch3
+ on m neg on cl
Draw the structure of N-ethyl-5-methyl-3-hexanamine.
two hexagon together on left no line to h3c bottom h on right outer line out and v connect ch3 and ch3 with end to ch3
Fluorine is more electronegative than chlorine yet the carbon-fluorine bond in CH3-F is shorter than CH3-Cl
Chlorine is a larger atom than fluorine and uses a 3p rather than 2p orbital. The overlap of a 2sp3 orbital with a 3p orbital is not as good as the overlap of a 2sp3 orbital with a 2p orbital, causing the bond to be longer and weaker.
Identify the compound with the highest bond angle.
the C-N-C bond in a quaternary amine
Identify the compound with the highest boiling point.
CH3CH2CH2CH2OH
Identify the compound(s) that do not have hydrogen bonding.
CH3CH2CH2CH2Cl and CH3CH2CH2OCH3
Which of the following will have the lowest boiling point?
CH4
Which of the compounds below will form hydrogen bonds between its molecules?
CH3NHCH2CH3
Which of the following has the greatest van der Waal’s interaction between molecules of the same kind?
ch3ch2ch2ch2ch3
Which of the following has the lowest boiling point?
CH3CH2CH2CH2CH2CH2CH3
Which of the following has the greatest solubility in CH3CH2CH2CH3?
(CH3)3CH
Which of the following is the most soluble in H2O?
CH3CH2OH
Which of the following would have the highest boiling point?
HO line CH2CH2CH2CH2 line OH
Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point?
2, 3-dimethylbutane < 2-methylpentane < n-hexane
What is the strongest intermolecular force present in liquid ethanol?
dipole-dipole, specifically hydrogen bonding
Assuming roughly equivalent molecular weights, which of the following would have the highest boiling point?
a quaternary ammonium salt
Explain why the molecule shown below has a lower boiling point than CH3CH2CH2CH3.
it has a greater contact area than isobutane
Primary and secondary amines exhibit hydrogen bonding; tertiary amines do not. Explain.
because nitrogen is not connected to hydrogen
Explain why trimethylamine, (CH3)3N:, has a considerably lower boiling point than propylamine CH3CH2CH2NH2, even though both compounds have the same molecular formula.
because boiling point is higher for propylamine
Which of the molecules below has the higher boiling point? Briefly explain your choice.
CH3CH2CH2OH
it is capable of intermolecular hydrogen bonding.
Would you expect sodium chloride (NaCl) to be highly soluble in the organic solvent hexane (CH3CH2CH2CH2CH2CH3)? Briefly explain your answer.
Nonpolar solvent molecules do not solvate ions well. The attractions of oppositely charged ions to each other are vastly greater than the weak attractions of the ions for the solvent.
Which compound is more soluble in water? Briefly explain your choice.
CH3CH2OH is more soluble in water since it can donate a hydrogen bond to water and accept a hydrogen bond from water
Which compound is more soluble in water? Briefly explain your choice.
(CH3)2NH is more soluble in water since it can hydrogen bond with water
Which intermolecular force is primarily responsible for the interactions among alkane molecules?
van de waal’s
What is polarizability and how is it related to the size of an atom?
Polarizability indicates the ease with which an electron cloud can be distorted larger atoms = loose nucleus = more distortion
Arrange the following amines in order of increasing boiling point, lowest bp to highest bp: (CH3)2CHCH2CH2NH2, (CH3)2CHN(CH3)2, and (CH3)2CHCH2NHCH3.
per CH3 closed 2CHN per CH3 closed 2 < per CH3 closed 2CHCH2NHCH3 < per CH3 closed 2CHCH2CH2NH2
The eclipsed and staggered forms of ethane are said to differ in ________.
conformation
Which of the following is the staggered conformation for rotation about the C1—C2 bond in the following structure?
one
Among the butane conformers, which occur at energy minima on a graph of potential energy versus dihedral angle?
gauche and anti
Which of the following best explains the relative stabilities of the eclipsed and staggered forms of ethane? The ________ form has the most ________ strain.
eclipsed; torsional
Which of the following best explains the reason for the relative stabilities of the conformers shown?
II has more torsional strain.
Which of the following statements about the conformers that result from rotation about the C2-C3 bond of butane is correct?
none
Draw the Newman projection that represents the most stable conformation of 3,3-dimethylhexane viewed along the C3-C4 bond.
circle peace sign top going right ch2ch3 to h to ch3 to ch2ch3 to h3c to h
Draw the Newman projection that represents the least stable conformation of 3,3-dimethylhexane viewed along the C3-C4 bond.
circle peace sign top to right ch2ch3 to h close to ch3 to h close to h3c to h3ch2c close
Draw the Newman structure for the most stable conformation of 1-bromopropane considering rotation about the C1-C2 bond.
circle peace sign from top to right br to h to h to ch3 to h to h
Draw a Newman projection of the most stable conformation of 2-methylpropane.
circle peace sign from top to right ch3 to h to ch3 to h to h to h
Define the term conformation.
Conformations are different arrangements of the same molecule formed by rotations about single bonds.
View a butane molecule along the C2-C3 bond and provide a Newman projection of the lowest energy conformer.
circle peace sign top to right ch3 to h to h to ch3 to h to h
Provide a representation of the gauche conformer of butane.
circle peace sign top to right ch3 to ch3 to h to h to h to h
Draw the Newman projection of the most stable conformation that results due to rotation about the C2-C3 bond in 2,3-dimethylbutane.
circle peace sign from top to right h to ch3 to ch3 to h to h3c to h3c
Identify the most stable conformation of butane.
anti
List the conformations in order of decreasing stability.
6 to 3 and 5 to 1 and 4 to 2
Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?
cyclohexane < cyclopentane < cyclobutane < cyclopropane
Describe the source of angle strain and torsional strain present in cyclopropane.
The angle strain arises from the compression of the ideal tetrahedral bond angle of 109.5° to 60°. The large torsional strain occurs since all C-H bonds on adjacent carbons are eclipsed.
Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?
chair < twist-boat < boat < half-chair
Which of the following is the most stable conformation of bromocyclohexane?
3
In the boat conformation of cyclohexane, the “flagpole” hydrogens are located on ________.
C-1 and C-4
Which conformer is at a local energy minimum on the potential energy diagram in the chair-chair interconversion of cyclohexane?
twist-boat
The Keq for the interconversion for the two chair forms of methylcyclohexane at 25 °C is 18. What % of the chair conformers feature an axial methyl group?
5
The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at Calculate the percentage of the axial conformer at the temperature.
Keq = eq over ax = 1.5

% axial ax over eq + ax = x 100%
= 1 over 1.5 + 1 x 100%
= 40%

Which of the following describes the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane?
The tert-butyl group is equatorial and the methyl group is axial.
Name the compound shown below.
side hour glass left top line to cl right top line to cl
cis-1,3-dichlorocyclohexane
Which of the following has two equatorial alkyl substituents in its most stable conformation?
cis-1,3-diethylcyclohexane
Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane.
side hour bottom dip line up ch3 right top line out c per ch3 closed 3
Draw the most stable conformer of cis-1-isopropyl-2-methylcyclohexane.
side hour top line up ch3 low line ch per ch3 closed 2
Draw the most stable conformation of trans-1-isopropyl-2-methylcyclohexane.
side hour top line ch per ch3 closed 2 bottom line out ch3
Identify the number of secondary hydrogens in the following structure.

look like a rat

8
Identify the compound where the groups are axial and equatorial.
cis-1,4-dibromocyclohexane
Identify the least stable conformation for 1-tert-butyl-3-methylcyclohexane
tert-butyl is axial and the methyl is axial.
Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.
side hour right top line out ch2ch3 bottom line out ch3
Draw the most stable conformer of trans-1-ethyl-2-methylcyclohexane.
side hour top right line out to ch2ch3 bottom line out to ch3
Draw the most stable conformer of cis-1-ethyl-3-methylcyclohexane.
side hour top right line out ch2ch3 low dip line down h3c
Draw the most stable conformer of trans-1-ethyl-3-methylcyclohexane.
side hour top right line out ch2ch3 bottom dip ch3
Draw the most stable conformer of cis-1-ethyl-4-methylcyclohexane.
side hour right top line out ch2ch3 left low line out ch3
Draw the most stable conformer of trans-1-ethyl-4-methylcyclohexane.
side hour top right line out ch2ch3 low left line out h3c
) What aspect of the fused ring systems present in cholesterol make it an ideal compound to lend rigidity to cell membranes?
The trans-fused ring systems present in cholesterol are not able to undergo chair-chair interconversion (ring flip). This renders them a high degree of conformational rigidity.
If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?
2n + 2
How many constitutional isomers are possible for C6H14?
5
What type of isomers are CH3CH2OCH3 and CH3CH2CH2OH?
constitutional
What is the relationship between the following compounds?
configurational isomers
What is the relationship between the following compounds?

with wedges

constitutional isomers
What is the relationship between the structures shown below?

hour glass

constitutional isomers
What is the relationship between the structures shown below?

pentagons

constitutional isomers
Identify the pair of compounds.

lines

configurational isomers
Which of the following cannot exhibit chirality?
1, 4-dibromobutane
Which of the following compounds is chiral?
h with 3 lines down to h with 2 t connects left both ch3 right is br and cl
Is the molecule shown below chiral or achiral?
square with wedge to oh
achiral
Is the molecule shown below chiral or achiral?
square with dark wedge up oh light wedge down oh
chiral
Is the molecule shown below chiral or achiral?

square dark wedges up to oh down oh

achiral
Is the molecule shown below chiral or achiral?

hexagon dark wedge right ch3 left wedge light oh

achiral
Identify the compounds that are not chiral.
a b d
Which of the following compounds has an asymmetric center?
3
How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?
How many asymmetric centers are present in the compound shown below?
two hexagon together light wedge middle is h and bottom middle dark wedge is h right top wedge dark ch per ch3 closed 2 left bottom two wedge light to h3c dark h3c
3
How many asymmetric centers are present in the compound below?

honey comb right top per ch3 closed 2n bottom 0 right cch3

5
Identify the pair of compounds.
configurational isomers
Give the number of asymmetric centers in limonene.
1
Identify the compound(s) with asymmetric centers.
cross shape with ch2ch2ch3 in bottom
A and B are stereoisomers. They are nonsuperimposable and are mirror images of one another. Which of the following best describes the relationship between A and B?
enantiomers
What is the relationship between the structures shown below?
left has cross ch3 bottom right has h in bottom
identical compounds
Which of the following compounds is an enantiomer of the structure below?
it doesnt have an enantiomer
Which of the following statements correctly describes the molecule shown below?
The mirror image of this molecule is its enantiomer.
Choose the enantiomer of the compound below.
e
The compound CH3CHClCH2CH=CHCH2CH3 contains only one asymmetric center. Explain why it has four stereoisomers.
In addition to the single asymmetric center which may be either R or S, it also contains a carbon-carbon double bond which may be either E or Z. Thus, the four stereoisomers can be designated E, R; E, S; Z, R; and Z, S.
Draw the enantiomer of the compound below.

up 4 swigs first dip dark wedge up oh sec dip wedge down br

down 4 swigs first dip wedge down oh sec dip up wedge to br
Identify the following compounds as R or S.
cross
horse
cross with f

all s

Identify all pairs of enantiomers.
mirror images
b and d
Identify all identical compounds.
look for mirror images
A and C
Which of the following compounds has an S configuration?
cross with ch2cl top cl bottom h on right ch3 on left
Which of the following compounds has an R configuration?
cross with h on top ch=ch2 bottom ch3ch2 left br right
Which of the following groups has the highest priority using the Cahn, Ingold, Prelog rules?
line to o line to ch3
The configuration of R-(+)-glyceraldehyde is as follows:
What is the absolute configuration of (-)-lactic acid?
R configuration
Indicate whether each of the following structures has the R or S configuration. What is the relationship between the two structures?
top br is 1 left 2 bot 3 right 4 is r
top oh is 2 right 1 bottom 4 left 3 is s
both are enantiomers
Label each asymmetric center in the compound below as R or S.
hexagon low right dark wedge oh light wedge ch3
s at dark wedge oH
Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate three-dimensional stereochemistry detail properly.
up 3 swigs first dip two wedges dark is br light is h
Provide the structure of (R)-4-octanol. Be careful to indicate proper stereochemistry.
up h3c 7 swigs end ch3 3rd dip two wedges left light h right dark oh
Identify the following compounds as R or S. crosses
h top is r
oh top is s
br top is r
Provide a careful structure for (2R,3S)-2,3-dibromohexane.
h3c up 5 swigs end ch3 first dip dark wedge br sec dip light wedge br
Provide a careful structure for (2S,3S)-2,3-dibromohexane.
h3c up 5 swigs end ch3 first and sec dip light wedge br
Provide a careful structure for (2S,3R)-2,3-dibromohexane.
h3c up 5 swigs end ch3 first dip light wedge br sec dip dark wedge br
Label each asymmetric center as R or S.
looks like a rat with h and cl on right
s next to triangle
r at bottom dip
s between h and cl
Provide a careful structure for (2R,3S,4S)-2-bromo-4-methyl-3-hexanol.
up 5 swigs first dip dark wedge br sec dip down light wedge oh third dip up dark wedge ch3
Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
up 5 swigs first dip light wedge br sec dip down light wedge oh third dip up light wedge ch3
Which of the following is a true statement?
A mixture of achiral compounds will be optically inactive.
Which of the following is not true of enantiomers?
They have the same specific rotation.
Which of the following is/are optically inactive?
all the above
Which of the following statements correctly pertains to a pair of enantiomers?
They rotate the plane of polarized light by exactly the same amount and in opposite directions.
If (S)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (R)-glyceraldehyde?
+8.7°
A mixture of equal amounts of two enantiomers ________.
is called a racemic mixture
is optically inactive
both
A solution containing 0.96 g of 2-bromooctane in 10 mL ether solution gave an observed rotation of -1.8° in a 10 cm cell at Calculate the specific rotation of this solution.
[?] t over d = a over 1c

[?] 20 degrees c over d = 1dm times .96 g over 10 ml = -18.75° in ether

A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?
+2.57°
Twenty grams of a compound was dissolved in 100 mL of solvent and gave an observed rotation of -20 degrees. The sample tube is 4 dm long. Calculate the specific rotation.
-25°

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