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MCAT Ochem > Ch 1 - Nomenclature > Flashcards

Ch 1 - Nomenclature Flashcards

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MCAT flashcards
1
Q

What is the parent chain?

A
  • longest carbon chain containing the highest-order functional group
  • determines the root of the name
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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
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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
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4
Q

How do bonds affect priority of functional groups?

A

the double bond takes precedence over the triple bond

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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

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6
Q

What determines the suffix of the compound?

A

only the highest priority functional group and must be part of the parent chain

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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
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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
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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
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10
Q

What are hydrocarbons?

A
  • compounds that contain only carbon and hydrogen atoms
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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
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12
Q

What are alkenes and alkynes?

A
  • end in -ene (double bond) and -yne (triple bond)
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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
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14
Q

What are 2 examples of alcohols with common names?

A
  • ethyl alcohol = ethanol

- isopropyl alcohol = 2-propanol

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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
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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
Q

How are aldehydes named?

A
  • 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
Q

What are the most common ketones and the IUPAC name?

A
  • propanone = acetone
27
Q

What has the highest precedence: double bond, alcohol, aldehyde?

A

aldehyde

28
Q

When and how are prefixes used with aldehydes and ketones?

A
  • in a more complex molecule with a higher priority that takes precedence over the carbonyl, name substituents using oxo-
  • sometimes ketones use keto-
29
Q

How are carbons named relative to the carbonyl groups of aldehydes and ketones?

A
  • the carbon adjacent to the carbonyl carbon on both sides is the alpha
  • then the beta, gamma, and delta
30
Q

What are carboxylic acids?

A
  • 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
Q

How are carboxylic acids named?

A
  • 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
Q

What are the 3 most common carboxylic acids and their IUPAC name?

A
  • formic acid = methanoic acid
  • acetic acid = ethanoic acid
  • propionic acid = propanoic acid
33
Q

What are esters?

A
  • derivative of carboxylic acid

- the hydroxyl group (-OH) is replaced with an alkoxy group (-OR) where the R is a hydrocarbon chain

34
Q

How are esters named?

A
  • 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
Q

What are amides?

A
  • 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
Q

How are amides named?

A
  • 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
Q

What are anhydrides?

A
  • derivative of carboxylic acid
  • in the formation of an anhydride from 2 carboxylic acid molecules, one water molecule is removed
  • many are cyclic
38
Q

How are anhydrides named?

A
  • 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
Q

What is the hierarchy of priority of the functional groups and their prefix/suffix?

A
  • 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_

MCAT Ochem (12 decks)

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