Nomenclature

Creating this from the Kaplan books. I am reading a chapter then creating flashcards from what I think is important to know for the exam

What are the steps to naming a compound?

What are the steps to naming a compound?

1. identify parent chain

2. number the chain

3. name substituents

4. assign number to each substituent

5. complete name

Which chain is the parent chain if there is more than one of equal length connected?

the more substituted chain

Where is C1 when there is a highest order functional group?

C closest to the high-priority functional group

Where is C1 if all substituents are of equal priority?

Where the substituents have the lowest numbers

If double/triple bonds have a tie for lowest number, which takes priority?

double bond

How do you name alkanes?

replace -ane with -yl

How do you name substituents that occur multiple times?

Use prefixes: di-, tri-, tetra-

What is the common name?

t-butyl

What is the common name?

neopentyl

What is the common name?

isopropyl

What is the common name?

sec-butyl

What is the common name?

isobutyl

How do you number the substituents?

It is the same as the C they are attached to

How do you put the name together?

• substituents are placed in abc order

• number goes in front of substituent

• numbers are separated by commas

• words are separated by dashes

• finish with parent chain name including highest functional group

What is the name of this compound?

4-ethyl-5-isopropyl-3,3-dimethyloctane

What is a hydrocarbon?

molecule that only contains C and H

What is an alcohol?

molecule that contains at least one -OH group

What is the general formula for hydrocarbons?

CnH(2n+2)

How do you name alkyl halides?

prefix: fluoro-, chloro-, bromo-, iodo-

How do you name double bonds?

replace -ane with -ene

How do you name triple bonds?

replace -ane with -yne

Which number in the double/triple bond gets added to the name?

whichever is lower

What is the alkane nomenclature for 1-8C chains?

1. methane

2. ethane

3. propane

4. butane

5. pentane

6. hexane

7. heptane

   1. octane

How do you name alcohols?

replace -e with -ol

What is the prefix for alcohols if they’re not the highest functional group?

hydroxy-

What is the name?

ethanol

What is the name?

5-methyl-2-heptanol

What is the name?

6-hepten-1-ol

What is the common name formula for alcohols?

alkyl group + alcohol

What is the common name?

isopropyl alcohol

How do you name an alcohol with 2 hydroxyl groups?

replace -ol with -diol and add both numbers to front

What is a geminal diol?

alcohol with two hydroxyl groups on the came C

What is a vicinal diol?

alcohol with two hydroxyl groups on adjacent Cs

What is another name for geminal diols?

hydrates

Why are geminal diols not commonly seen?

they spontaneously dehydrate to create a carbonyl compound (has C=O)

What’s the difference between aldehydes and ketones?

aldehydes are on terminal C while ketones are on a C in the middle of the chain

How do you name an aldehyde?

replace -e with -al

What is the name?

butanal

What is the name?

5,5-dimethylhexanal

What is the common name?

formaldehyde

What is the common name?

acetaldehyde

What is the common name?

propionaldehyde

How do you name a ketone?

replace -e with -one

What is the common name formula for ketones?

alkyl groups in ABC order + ketone

What is the name?

2-pentanone

What is the IUPAC name

IUPAC: 2-propanone

What is the common name using the formula?

dimethylketone

What is the common name?

acetone

What is the prefix for aldehydes if not highest priority?

oxo-

What is the prefix for ketones if not highest priority?

keto- or oxo-

With carbonyls, how else may the adjacent Cs be named?

greek letters

alpha ⍺ → beta β → gamma 𝛄 → delta 𝛅

What is the IUPAC and common name?

IUPAC: 3-butene-2-one

Common: methylvinylketone

What is a Carboxylic Acid?

terminal COOH

How do you name carboxylic acids?

replace -e with -oic acid

What is the common name?

formic acid

What is the common name?

acetic acid

What is the common name?

propionic acid

What is an ester?

COOR

What is the R group in an ester?

hydrocarbon chain

How do you name an ester?

first term: alkyl name of R group

second term: parent acid with -oate instead of -oic acid

What is the name?

ethyl propanoate

What is the name?

propyl methanoate

What is the name?

methyl butanoate

What is an amide?

CONR

How many R groups can there be in an amide?

up to 3

How do you number the R groups in an amide?

N instead of a number

How do you name an amide?

first term: alkyl groups attached to N

second term: parent acid with -amide suffix

What is the name?

N-ethyl-N-methylbutanamide

What is the name?

propanamide

What is the name?

N,N-dimethylethanamide

What is an anhydride?

2 carboxylic acids attached with a water removed

What is the structure of most anhydrides?

cyclic

How do you name a symmetric anhydride?

replace -acid with -anhydride

How do you name an asymmetric anyhydride?

name both acids followed by anhydride

What is the name?

ethanoic propanoic anhydride

What is the IUPAC and common name?

IUPAC: ethanoic anhydride

Common: acetic anhydride

What is the priority list of functional groups from highest to lowest?

1. carboxylic acid

2. anhydride

3. ester

4. amide

5. aldehyde

6. ketone

7. alcohol

8. alkene

9. alkyne

10. alkane

What is the prefix and suffix of carboxylic acids?

prefix: carboxy-

suffix: -oic acid

What is the prefix and suffix of anhydrides?

prefix: alkyloxycarbonyl-

suffix: -anhydride

What is the prefix and suffix of esters?

prefix: alkoxycarbonyl-

suffix: -oate

What is the prefix and suffix of amides?

prefix: carbamoyl- or amido-

suffix: -amide

What is the prefix and suffix of aldehydes?

prefix: oxo-

suffix: -al

What is the prefix and suffix of ketones?

prefix: oxo- or keto-

suffix: -one

What is the prefix and suffix of alcohols?

prefix: hydroxy-

suffix: -ol

What is the prefix and suffix of alkenes?

prefix: alkenyl-

Suffix: -ene

What is the prefix and suffix of alkynes?

prefix: alkenyl-

suffix: -yl

What is the prefix and suffix of alkanes?

prefix: alkyl-

suffix: -ane

What is a structural isomer?

Two molecules that have the same formula

What must be the same for structural isomers?

Molecular weight

For structural isomers, are chemical properties same or different?

different

For structural isomers, are physical properties same or different?

Different

What kind of isomer are these?

Structural

What are stereoisomers?

share same atomic connectivity but differ in 3D orientation

What are conformational isomers?

molecules that differ in rotation around a single bond

What are configurational isomers?

molecules that can only be interconverted by breaking a bond

What is a good way to visualize conformational isomers?

Newman Projections

Where is a Newman projection visualized?

along line extending through C-C bond axis

What conformation is the lowest energy-state for straight-chain conformational isomers?

anti conformation

What is staggered conformation?

No overlap of atoms along line of sight

What is Anti Conformation?

Two largest groups are in same plane but on opposite sides