Organic CHEM: Weeks 1-3

Question 1

What are the steps of IUPAC naming?

Answer 1

1. Find the longest hydrocarbon chain.
2. Number the chain.
3. Name the substituents.
4. NUmber the substituents.
5. Create full name with substituents in alphabetical order.

Question 2

The highest priority functional group (substituent) will be:

Answer 2

The most oxidized.

Question 3

If a molecule presents with two or more hydrocarbon chains of equal length, which factor will determine which is the parent chain?

Answer 3

The most substituted chain will be the parent chain.

Question 4

Does the oxidation state increase or decrease with more bonds to heteroatoms?

Answer 4

Increases (single atoms like O, N, S, bonded to carbon chain)

Question 5

Does oxidation state increase or decrease with more bonds to hydrogen?

Answer 5

Decreases.

Question 6

When will an alkene take priority over a alkyne in IUPAC naming?

Answer 6

When in a ring.

Question 7

The highest priority substituent on a molecule will determine what?

Answer 7

It’s suffix.

Question 8

True or false: IUPAC rules name substituents in alphabetical order, where hyphenated prefixes are taken into consideration.

Answer 8

FALSE: Name in alphabetical order where hyphenated prefixes are not considered, while non-hyphenated prefixes (iso, neo, cyclo) are considered.

Question 9

Define alkane:

Answer 9

A hydrocarbon molecule with no double/triple bonds. The suffix of these molecules will be -ane. Ex: Hexane (C6H14)

Question 10

Define alkyl halide:

Answer 10

An alkane with a halogen substituent - Flouride, chloride, iodide, bromide, astatine, tennesine.

Question 11

Define alkene:

Answer 11

A hydrocarbon molecule with double bonds, suffix is changed to -ene.

Question 12

Define alkyne:

Answer 12

A hydrocarbon molecule with triple bonds, suffix is changed to -yne.

Question 13

If there is an alcohol substituent, what will the suffix change to?

Answer 13

-ol (methanol)

Question 14

What is it called when a molecule has two alcohol groups attached to it?

Answer 14

Diol.

Question 15

Compare a vicinal diol and a geminal diol:

Answer 15

1. Vicinal diols have two OH groups, which are on neighboring carbons.
2. Geminal diols have two OH groups, which originate from the same carbon.

Question 16

What is another name for geminal diols? Why is this not often seen?

Answer 16

Hydrates, which are not commonly seen as they easily lose a water molecule to form a alkene carbonyl.

Question 17

In a molecule with two double bonds adjacent to each other and an alcohol, which substituent takes priority?

Answer 17

The alcohol.

Question 18

What is the highest priority substituent on the MCAT?

Answer 18

Carboxylic acids

Question 19

**Common name for 2-propanol:

Answer 19

Isopropyl alcohol.

Question 20

**Common name for ethanol:

Answer 20

Ethyl alcohol.

Question 21

How do we distinguish between aldehydes and ketones?

Answer 21

1. Aldehydes: Are at the termination of a hydrocarbon chain - binding to at least one hydrogen.
2. Ketones: Are in the middle of a hydrocarbon chain - binding to carbon on either side.

Question 22

What will the suffix change to in aldehydes?

Answer 22

-al (Butanal)

Question 23

Common name for methanal:

Answer 23

Formaldehyde.

Question 24

Common name for ethanal:

Answer 24

Acetaldehyde.

Question 25

Common name for propanal:

Answer 25

proprionaldehyde

Question 26

What do we call an aldehyde sugar?

Answer 26

Aldoses.

Question 27

What do we call a ketone sugar?

Answer 27

Ketoses.

Question 28

What will the suffix change to in a ketone?

Answer 28

-one (2-pentone)

Question 29

If there is a substituent with higher priority than an aldehyde or ketone, what prefix should we give to the ketone/aldehyde?

Answer 29

1. Aldehyde = oxo- 2. Ketone = Oxo- or Keto-

Question 30

What is the common name for propanone?

Answer 30

Acetone.

Question 31

What will the suffix change to in a carboxylic acid?

Answer 31

-oic acid. (valproic acid)

Question 32

Common name for methanoic acid?

Answer 32

Formic acid.

Question 33

Common name for ethanoic acid?

Answer 33

Acetic acid.

Question 34

Common name for propanoic acid?

Answer 34

Propionic acid.

Question 35

Define an ester:

Answer 35

A carboxylic acid molecule, where the OH is replaced with an O-R. (Aloxy group).

Question 36

How are esters names?

Answer 36

The first word is the esterified group (O-R), the second word is the name of the parent carboxylic acid - suffix being -oate instead of -oic acid.

Question 37

Define an amide:

Answer 37

A carboxylic acid where the OH is replaced by a nitrogen - that may be unsubstituted or substituted. The suffix will change to -amide.

Question 38

In IUPAC naming how do we distinguish the substituents that are bound to the nitrogen?

Answer 38

Placing a N in front of their name. (N-ethylpropanamide)

Question 39

Define an anhydride:

Answer 39

A molecule formed by the combination of two carboxylic acids, where H2O is removed. Suffix will change to anhydride.

Question 40

If an anhydride is unsymmetrical, what must change in naming?

Answer 40

Each carboxylic acid will be named before the word anyhydride (ethanoic propanoic anhydride)

Question 41

Functional groups ranked in priority:

Answer 41

1. Carboxylic acids. 2. Anhydrides. 3. Esters. 4. Amides. 5. Aldehydes. 6. Ketones. 7. Alcohol. 8. Alkane/alkene/alkyne.

Question 42

1 carbon molecule

Answer 42

met-

Question 43

2 carbon molecule:

Answer 43

Eth-

Question 44

3 carbon molecule:

Answer 44

Prop-

Question 45

4 carbon molecule:

Answer 45

But-

Question 46

5 carbon molecule:

Answer 46

Pent-

Question 47

6 carbon molecule:

Answer 47

Hex-

Question 48

7 carbon molecule:

Answer 48

Hept-

Question 49

8 carbon molecule:

Answer 49

Oct-

Question 50

9 carbon molecule:

Answer 50

Non-

Question 51

10 carbon molecule:

Answer 51

Dec-