Ch 1 - Nomenclature Flashcards
1
Q
What is the parent chain?
A
- longest carbon chain containing the highest-order functional group
- determines the root of the name
2
Q
How do you number a carbon chain?
A
- the carbon numbered 1 will be the one closest to the highest priority functional group
- the highest priority functional group should have the lowest possible number; if all substituents have the same priority, make their numbers as low as possible
3
Q
What are heteroatoms and how do they affect oxidation state?
A
- atoms beside carbon and hydrogen (like oxygen, nitrogen, phosphorous, and halogens)
- oxidation state increases with more bonds to heteroatoms and decreases with more bonds to hydrogen
4
Q
How do bonds affect priority of functional groups?
A
the double bond takes precedence over the triple bond
5
Q
What are substituents and how are they named?
A
- functional groups that are not part of the parent chain
- name is placed at the beginning of the compound name as a prefix followed by the name of the longest chain
6
Q
What determines the suffix of the compound?
A
only the highest priority functional group and must be part of the parent chain
7
Q
How do you assign a number to each substituent?
A
- pair the named substituents to the corresponding numbers in the parent chain
- multiple of the same type will get prefixes, even if they are on the same carbon
8
Q
How to complete the name of a compound?
A
- names always begin with the names of the substituents in alphabetical order (ignore number and hyphenated prefix), with each preceded by its number
- numbers separated by commas and words with hyphens
- finish with the name of the backbone chain, including the suffix for the functional group of highest priority
9
Q
What are the steps of IUPAC nomenclature?
A
- find the longest carbon chain
- number the chain
- name the substituents
- assign number to each substituent
- complete the name
10
Q
What are hydrocarbons?
A
- compounds that contain only carbon and hydrogen atoms
11
Q
What are alkanes and how are the named?
A
- simple hydrocarbon molecules with the formula CnH(2n+2)
- methane (1 carbon)
- ethane (2 carbon)
- propane (3 carbon)
- butane (4 carbon)
- from 5-12 they follow the prefix greek root: pentane, hexane, heptane, octain, nonane, decane, undecane, dodecane
12
Q
What are alkenes and alkynes?
A
- end in -ene (double bond) and -yne (triple bond)
13
Q
How are alcohols named?
A
- named by replacing the -e at the end of the name of the corresponding alkane with the suffix -ol
- chain numbered so that the carbon attacked to the OH group gets the lowest possible number, even when there is multiple bonds
14
Q
What are 2 examples of alcohols with common names?
A
- ethyl alcohol = ethanol
- isopropyl alcohol = 2-propanol
15
Q
What are diols?
A
- also termed glycols
- alcohols with 2 OH groups
- indicated with the suffix -diol
- when naming, must number each OH group
16
Q
What is the difference between geminal diols and vicinal diols?
A
- Vicinial diols are in the Vicinity of each other, on adjacent carbons; Geminal diols - like Gemini twinss - are paired on the same carbon
- geminal: diols with OH groups on the same carbon (not commonly seen because they spontaneously dehydrate to produce carbonyl compounds with the functional group C=O
- vicinal: diols with OH groups on adjacent carbons
17
Q
Why do alcohols take precedence over multiple bonds?
A
alcohols are more oxidized than multiple bonds, so they take priority in nomenclature and are indicated with the suffix -ol
18
Q
What is a carbonyl group?
A
- a carbon double-bonded to an oxygen
19
Q
What does chain-terminating mean?
A
- appear at the end of the parent chain
20
Q
What are the differences and similarities between an aldehyde and a ketone?
A
- differ in the placement of the carbonyl group; aldehydes are chain-terminating and ketones are found in the middle of the carbon chain
- they both do not have any leaving groups connected to the carbonyl carbon, they are only connected to alkyl chains or H
21
Q
What are aldehydes?
A
- have a carbonyl group found at the end of the carbon chain
- generally attached to carbon number 1 since terminal
22
Q
What are 3 most common aldehydes and their IUPAC name?
A
- formaldehyde = methanal
- acetalaldehyde = ethanal
- propionaldehyde = propanal
23
Q
What are ketones?
A
- contain a carbonyl group somewhere in the middle of the carbon chain
- always have to assign a number to the carbonyl carbon
24
Q
How are ketones named?
A
- by replacing the -e in the name of the parent alkane with the suffix -one
- give the carbonyl the lowest possible number
25
How are aldehydes named?
- by replacing the -e of the parent alkane with the suffix -al
- when at position 1, do not need to include this number in the chemical name
26
What are the most common ketones and the IUPAC name?
- propanone = acetone
27
What has the highest precedence: double bond, alcohol, aldehyde?
aldehyde
28
When and how are prefixes used with aldehydes and ketones?
- in a more complex molecule with a higher priority that takes precedence over the carbonyl, name substituents using oxo-
- sometimes ketones use keto-
29
How are carbons named relative to the carbonyl groups of aldehydes and ketones?
- the carbon adjacent to the carbonyl carbon on both sides is the alpha
- then the beta, gamma, and delta
30
What are carboxylic acids?
- contain both a carbonyl group (C=O) and a hydroxyl group (-OH) on a terminal carbon
- terminal function group, therefore their carbon is usually position 1
31
How are carboxylic acids named?
- by replacing the -e at the end of the parent alkane with the suffix -oic acid
- highest priority therefore all other groups are named as substituents using prefixes
32
What are the 3 most common carboxylic acids and their IUPAC name?
- formic acid = methanoic acid
- acetic acid = ethanoic acid
- propionic acid = propanoic acid
33
What are esters?
- derivative of carboxylic acid
| - the hydroxyl group (-OH) is replaced with an alkoxy group (-OR) where the R is a hydrocarbon chain
34
How are esters named?
- first term is the alkyl name of the esterfying group (R)
- second term is the name of the parent acid with -oate replaced -oic acid
- groups bonded directly to the ester oxygen are named as substituents and are not numbered
35
What are amides?
- derivative of caboxylic acid
- the hydroxyl group (-OH) is replaced with an amino group (nitrogen-containing group)
- amino nitrogen can be bonded to 0, 1, or 2 alkyl groups
36
How are amides named?
- first term is the amino group
- second term is the name of the parent acid with -amide replaced -oic acid
- substituents attached to the nitrogen atom are labeled with capital N- (not numbered), indicating that this group is bonded to the parent molecule via a nitrogen
37
What are anhydrides?
- derivative of carboxylic acid
- in the formation of an anhydride from 2 carboxylic acid molecules, one water molecule is removed
- many are cyclic
38
How are anhydrides named?
- replacing acid with anhydride in the name corresponding carboxylic acid if the anhydride is formed from only one type of carboxylic acid
- if the anhydride is not symmetrical, both carboxylic acids are named with the suffix -acid before anhydride is added to the name
39
What is the hierarchy of priority of the functional groups and their prefix/suffix?
- carboxylic acid (carboxy-, -oic acid)
- anhydride (alkanoloxycarboyl-, anhydride)
- ester (alkoxycarbonyl-, -oate)
- amide (amido-, -amide)
- aldehyde (oxo-, -al)
- ketone (oxo-, keto-, -one)
- alcohol (hydroxy-, -ol)
- alkene (alkenyl-, -ene)
- alkyne (alkynyl-, -yne)
- alkane (alkyl-, -ane_
