Structure

Question 1

How do you determine the acidity of a compound?

Answer 1

Comparing acidity of organic molecules can be accomplished by looking at the stability of their conjugate base.

Question 2

Which is more acidic and why: Phenol or Cyclohexanol

Answer 2

Phenol is more acidic. The conjugate base of phenol has more resonance delocalization of its negative charge than cyclohexanol, which means that phenol has a more stable conjugate base and is more acidic than cyclohexanol.

Question 3

Put the following in order of increasing acidity:

Phenol, benzoic acid, cyclohexanol

Answer 3

Most acidic: Benzoic acid, then Phenol, then cyclohexanol

Question 4

R-COOH

Answer 4

Carboxylic Acid

Question 5

R-COO-R

Answer 5

Ester

Question 6

R-CO-X

Answer 6

Acid Halide

Question 7

R-CO-NR2

Answer 7

Amide

Question 8

R-CHO

Answer 8

Aldehyde

Question 9

R-C=O-R

Answer 9

Ketone

Question 10

R-OH

Answer 10

Alcohol

Question 11

R-SH

Answer 11

Thiols

Question 12

NR3

Answer 12

Amine

Question 13

Name the compound

Answer 13

4-penten-2-ol

Question 14

Name the compound:

Answer 14

Butanoic Acid

Question 15

Answer 15

4-Hydroxy-3-methylbutanoic acid. If we follow IUPAC naming conventions, the highest-priority group on this molecule is the carboxylic acid because it has the highest oxidation state. We thus know that the rightmost carbon should be given the number “1” and that the suffix should be “-oic acid.” The other functional groups (“hydroxy” and “methyl”) are then listed in alphabetical order with the numbered carbon to which they are attached.

Question 16

List the following from lowest to highest priroity in IUPAC naming and how did you know:

alcohol, carboxylic acid, aldehyde, amine

Answer 16

amine, then alcohol, then aldehyde, and finally carboxylic acid. It goes from least to most oxidized

Question 17

Name the compound:

Answer 17

trans-4-methyl-2-hexene. The double bond takes priority when numbering.The parent chain is six carbons long, giving us the “hex” root. Since there is a double bond, it will have the “-ene” suffix. The double bond should be at the lowest number carbon possible, so numbering begins at the left end of the parent chain, and the alkene therefore begins at the second carbon. Because the two hydrogens are on opposite sides of the alkene double bond, it is in the trans configuration.

Question 18

Name the following compound:

Answer 18

3-methyl-4-pentyne-2,3-diol

Question 19

Why does hydrogenation of the following compound release 120 kj but if you were to hydrogenate benzene it wouldnt release 120 x 3?

Answer 19

The following wouldn’t happen. It would only release about 200 kJ/mol because benzene is resonance stabilized. Resonance made the internal energy of benzene lower so it had less energy available to release.

Question 20

Why are carboxylic acids stronger than alcohols?

Answer 20

Resonance stabilization

Question 21

What is the definition of aromatic?

Answer 21

Aromatic compounds are those that contain planar, conjugated rings and follow Hückel’s rule, which stipulates that the system must possess 4n + 2 pi electrons

Question 22

Considering only carbon-carbon bonds, how does the bond length between ring carbons on the structure differ from the length of the single bonds outside of the ring?

Answer 22

The ring component of serotonin is aromatic; additionally, it displays resonance, allowing each C-C bond to display a bond order of 1.5. In other words, these bonds are halfway between single and double bonds. Higher order bonds have a greater bond energy than single bonds - that means that the heat energy required to break the bond is greater (with triple bonds requiring the most energy). Remember, bonds with higher bond dissociation energies are shorter and stronger.

Question 23

What are the bond orders for single, double, and triple bonds?

Answer 23

In a covalent bond between two atoms, a single bond has a bond order of one, a double bond has a bond order of two, a triple bond has a bond order of three, and so on

Question 24

Name the structure:

Answer 24

2,2-dichloro-3-phenylpropanoic acid

Question 25

Why would 1,3,5-Hexatriene release less energy upon hydrogenation when compared to 1,2,3-Hexatriene?

Answer 25

!,3,5-Hexatriene is a conjugated system

Question 26

True or False: Carboxylic acids are stronger acids than phenols because of their resonance stabilization in the conjugate base form

Answer 26

True

Question 27

Identify the arrangement

Answer 27

Sec-butyl

Question 28

How do the presence of double and triple bonds impact reactivity of hydrocarbons?

Answer 28

Hydrocarbon reactivity increases as electron density is increased. Double bonds increase electron density and triple bonds increase it even more. So molecules with triple bonds will be more reactive than those with double bonds and those with only single bonds will be the least reactive.

Question 29

How do you identify a conjugated system?

Answer 29

Alkenes with alternating carbon-carbon double bonds form conjugated systems. 1,3,5-hexatriene has alternating double bonds, making it a conjugated system also 2,4,6-heptatriene has alternating double bonds, making it a conjugated system.

Question 30

True or False: Decreasing the amount of bonds to oxygen can be considered a reduction

Answer 30

True

Question 31

Ethene is exposed to H2 in a solution containing a chunk of solid palladium. If it reacts successfully, the original alkene will…

Answer 31

Be reduced to ethane

Question 32

A 5 carbon alkane would have what prefix?

Answer 32

Penta

Question 33

A 7 carbon alkane would have what prefex?

Answer 33

Hepta

Question 34

A 9 carbon alkane would have what prefex?

Answer 34

non-

Question 35

A 10 carbon alkane would have what prefex?

Answer 35

dec-

Question 36

Identify the group arrangements on the molecule

Answer 36

Question 37

Identify the branched substituent

Answer 37

isopropyl