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O1 Review Questions Update .pdf


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Title: Basics and Isomerism Review Questions
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O-Chem Day 1 Review Questions
1) What is the name of the following molecule:

A)
B)
C)
D)

2-propyl-4-methylhexane
4,6-dimethyloctane
3,5-dimethyloctane
4,6-diethyloctane

2) What is the name the following molecule?
Br

A)
B)
C)
D)

1-methyl-2-ethyl-4-bromocyclohexane
1-bromo-3-ethyl-4-methylcyclohexane
5-bromo-2-ethyl-1-methylcyclohexane
4-bromo-1-ethyl-2-methylcyclohexane

3) What is the name of the following molecule?

A)
B)
C)
D)

3-ethyl-2,2,4,5-tetramethylheptane
3-tert-butyl-4,5-dimethylheptane
3,4-dimethyl-5-tert-butylheptane
3,5-diethyl-2,2,4-trimethylhexane

4) What is the name of the following molecule?
O

O

A)
B)
C)
D)

phenylethanoate
ethyl benzoate
ethoxybenzenone
phenylpropanoate

5) What is the name of the following molecule?
O

O

A)
B)
C)
D)

2-methoxycyclopentanone
methylcylcopentanoate
methoxycylcopentanal
2-methoxy-1-pentanone

6) How many sigma bonds are in the following molecule?
O

A)
B)
C)
D)

24
25
26
27

7) How many pi bonds are in the following molecule?
O

A)
B)
C)
D)

3
4
5
6

8) What are the hybridization and bond angles respectively around the indicated atom?
O

A)
B)
C)
D)

sp3, 109.5°
sp3, 120°
sp2, 109.5°
sp2, 120°

9) What are the hybridization and bond angles respectively around the indicated atom?

H

N

H

H

A)
B)
C)
D)

sp3, 109.5°
sp3, 120°
sp2, 109.5°
sp2, 120°

10) Which of the following has the highest boiling point?
A)
B)
C)
D)

CH3CH2CH2F
CH3CH2CH3
CH3CH2CH2OH
CH3CH2CH2CH3

11) Which of the following has the lowest boiling point?
A)
B)
C)
D)

CH3CH2CH2F
CH3CH2CH3
CH3CH2CH2OH
CH3CH2CH2CH3

12) Which of the following has the highest boiling point?

A)

B)
C)

D)

13) Which of the following is most soluble in H2O?
A)
B)
C)
D)

CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2CH2OH
HOCH2CH2CH2CH2OH
CH3CH2CH2CH2OH

14) Which of the following is most soluble in benzene (C6H6)?
A)
B)
C)
D)

CH3CH2CH2OH
CH3CH2OH
HOCH2CH2OH
CH3CH2CH2CH2OH

15) Which of the following is the strongest acid?
O

A)

OH

OH

B)

O

OH
F

C)

D)

O

OH

Cl

16) Which of the following is the strongest base?
O

A)
S

B)
O
O
S

C)

O
O

O

D)

17) How are the following two compounds related?

OH

A)
B)
C)
D)

OH

same compound
enantiomers
diastereomers
different compounds

18) How are the following two compounds related?
Br

Br

A)
B)
C)
D)

same compound
enantiomers
diastereomers
different compounds

19) How are the following two compounds related?
O

O

H

HO
H

H

H

OH

OH

H

OH
CH3

CH3

A)
B)
C)
D)

H

same compound
enantiomers
diastereomers
different compounds

20) How are the following two compounds related?
CH3

CH3

H

Br

Br

H

H

Br

Br

H

CH3

A)
B)
C)
D)

same compound
enantiomers
diastereomers
different compounds

CH3

O-Chem Day 1 Answer Key
1) What is the name of the following molecule:

A)
B)
C)
D)

2-propyl-4-methylhexane
4,6-dimethyloctane
3,5-dimethyloctane
4,6-diethyloctane
4

2
3

methyl

5

1
6

7

methyl

8

The longest carbon chain is 8. Numbering it as above the 1st substituent is at carbon 3; had we
numbered the chain the other way the 1st substituent would have been at carbon 4 so the lower
number wins. Finally, there are methyl substituents at carbons 3 and 5 and hence choice C is the
correct answer.
2) What is the name the following molecule?
Br

A)
B)
C)
D)

1-methyl-2-ethyl-4-bromocyclohexane
1-bromo-3-ethyl-4-methylcyclohexane
5-bromo-2-ethyl-1-methylcyclohexane
4-bromo-1-ethyl-2-methylcyclohexane
4

5

Br

4

6

Br

5

3

2

3

Br

1
4

2

1

6
5

1

6

3

2

B
C
D
First of all there is no way to number this so as to arrive at answer choice A so it is eliminated.
There are 3 possible ways of numbering the cyclohexane that will have the 1st substituent at
carbon-1 (choices B, C, and D). There are then 2 ways of numbering it to give the 2nd substituent
at carbon-2 (choices C and D) whereas B has the 2nd substituent at carbon-3 and is therefore
eliminated. Between choices C and D, choice D has the 3rd substituent at carbon-4 whereas
choice C has the 3rd substituent at carbon-5 and is therefore eliminated. Choice D ultimately
numbers so as to give the substituents successively the lowest numbers and is therefore the
proper way of numbering the chain. Don’t forget that we only use the alphabet to break a
numerical tie which was not the case in this question.

3) What is the name of the following molecule?

E)
F)
G)
H)

3-ethyl-2,2,4,5-tetramethylheptane
3-tert-butyl-4,5-dimethylheptane
3,4-dimethyl-5-tert-butylheptane
3,5-diethyl-2,2,4-trimethylhexane
methyl

ethyl

6

4
3

5
7

2

2
1

methyl

1

6

4
3

5
7

methyl

methyl

There is more than one way to number this to get the longest chain of 7 carbons. The proper way
is then to choose the way that has the most substituents. The correct way on the left has 5
substituents whereas the incorrect way on the right only has 3 substituents. The correct way is
then numbered so as to give the lowest number to the 1st substituent. Finally the substituents are
named in alphabetical order (ethyl before methyl) which leads us to A.
4) What is the name of the following molecule?
O

O

A)
B)
C)
D)

phenylethanoate
ethyl benzoate
ethoxybenzenone
phenylpropanoate
O

O

O

O

Esters are named after the carboxylate that is part of their structure (in this case the benzoate ion
shown to the right). First name the substituent that is attached to the oxygen of the carboxylate
(in this case an ethyl group) and then finish with the second word as the correct carboxylate
giving us ethyl benzoate.

5) What is the name of the following molecule?
O

O

A)
B)
C)
D)

2-methoxycyclopentanone
methylcylcopentanoate
methoxycylcopentanal
2-methoxy-1-pentanone

O
1

5

2

O

4
3

The ketone is the major functional group that will be named using a suffix (-one for a ketone) as
part of the main carbon chain and on a cyclic alkane is by default at carbon-1. The chain is then
numbered starting there to give the substituent (a methoxy group here) the lowest possible
number. And thus we arrive at 2-methoxycyclopentanone. And we don’t give the location of the
carbonyl because it had to be at carbon-1 by default as stated earlier.
6) How many sigma bonds are in the following molecule?
O

A)
B)
C)
D)

24
25
26
27
H

H

H

H

H

H

H

O

H

H
H
H H

H
H
H
H

To be careful, you should draw out all of the bonds to the hydrogens that aren’t shown in the
original structure. There are 24 single bonds, 2 double bonds and 1 triple bond. All single bonds
are sigma bonds and the 1st bond of a double or triple bond is always a sigma bond. The gives us
24+2+1=27.

7) How many pi bonds are in the following molecule?
O

A)
B)
C)
D)

3
4
5
6

All single bonds are sigma bonds and the 1st bond of a double or triple bond is always a sigma
bond but any additional bonds are pi bonds. Therefore a double bond is 1 sigma and 1 pi bond
and a triple bond is 1 sigma and 2 pi bonds. With 2 double bonds and 1 triple bond this molecule
has a total of 4 pi bonds.
8) What are the hybridization and bond angles respectively around the indicated atom?
O

A)
B)
C)
D)

sp3, 109.5°
sp3, 120°
sp2, 109.5°
sp2, 120°

The indicated atom has 3 electron domains. According to VSEPR theory, the bond angles will
be maximized and be ~120°. For 3 electron domains, the atom is sp2 hybridized. Ultimately,
with 3 electron domains it will need 3 hybrid orbitals and will need to mix 3 orbitals to make 3
hybrids. The 1st 3 orbitals available for making hybrids are an ‘s’ orbital and 2 ‘p’ orbitals,
hence sp2.


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