CH14 LEC: CMPNDS W/ O, S, OR HALOGENS

OSU BIOPHRM 3311

disulfide originates from what rxn?

oxidation of 2 thiols

Alpha Carbon (Cα) definition

the C atom directly attached to a functional group of interest

alpha Cα always had ___ bonds

4 single

alcohol functional group definition

an organic compound w/ an —OH group usually linked to a saturated C atom (AKA alpha C)

ID this structure

typical structure of an alcohol, where R, R’, R” can be H, alkyl group, or similar groups, alone or in combination

ID the family of this structure

alcohol

ID the family of this structure

alcohol (NOT phenol)

ID this structure

• phenol — not classified as an alcohol!

• no primary, secondary, or tertiary alcohols

aliphatic alcohols definition

organic compounds in which the —OH group is attached to an aliphatic C [straight-chain, branched, or non-aromatic ring structures]

alcohols are classified as ___, ___, and ___ according to the number of Cs substituents (alkyl or R-groups) bonded to the alpha C (—C—OH)

primary, secondary, tertiary

methanol’s (CH3OH) classification is considered ___ despite no alkyl group bond to the alkyl carbon

primary

phenol compound definition

alcoholic aromatic compound w/ an —OH group replacing 1 H atom in a benzene ring

benzene ring affects phenol’s ___ and ___, distinguishing it from aliphatic alcohols.

reactivity and properties

recognize this: C6H6

benzene

recognize this: C6H5OH or C6H6O

phenol

recognize this: —C—O—C— …or… —R—O—R—

ether

ether compound definition

any class of organic compounds that contains O b/t 2 alkyl or aryl groups (functional groups derived from aromatic ring)

aryl group definition

functional group derived from an aromatic ring

prefix in common naming of aliphatic alcohols: n—

indicates a straight chain

prefix in common naming of aliphatic alcohols: iso—

branch at second-to-last C (Y shape)

prefix in common naming of aliphatic alcohols: sec—

OH on a secondary C

prefix in common naming of aliphatic alcohols: tert—

OH on a tertiary C

prefix in common naming of aliphatic alcohols: neo—

C skeleton ends in quaternary C

naming common names of aliphatic alcohols: what do we add as the suffix?

“alcohol” — i.e., “alkyl alcohol”

naming common names of aliphatic alcohols: what number do we apply to the position of the —OH group?

the smallest number

naming alcohols — IUPAC names: alcohols are named by replacing the suffix “—ane” of alkanes w/ ___.

“—anol”

naming alcohols w/ alkyl substituent(s): the parent H—C chain includes the ___.

—OHs

naming alcohols w/ alkyl substituent(s): number the C atoms of the parent chain beginning at ___.

the end nearer the alcohol functional group — then the other substituent groups.

naming alcohols w/ alkyl substituent(s): add the location of the alcohol group by placing the number that locates the —OH group ___. 

immediately before the parent-suffix.

naming alcohols w/ alkyl substituent(s): name and number the positions of the alkyl substituents___.

after you have numbered the —OH group

• REMEMBER TO ALPHABETIZE 🙂

naming alcohols w/ alkyl substituent(s): for alcohols w/ 2 OH groups, name as ___.

alkanediol — keep the “e”.

naming alcohols w/ alkyl substituent(s): for alcohols w/ 3 OH groups, name as ___.

alkanetriol, and so on.

naming alcohols w/ alkyl substituent(s): the chain is numbered so as to give one of the —OH groups the ___.

lowest possible number

polyhydric alcohols definition

alcohols w/ 2 or 3 hydroxyl groups (—OH)

cyclic alcohols definition

alcohols w/ cyclic hydrocarbons chains

for cyclic alkanes and alkenes that contain an —OH group, name them as ___ and ___, respectively.

cycloalkanol and cycloalkenol

for cyclic alkanes/enes naming: the —OH is presumed to be bound to the ___ and proceeds in the direction that gives the other substituent(s) or functional groups the ___.

• 1st carbon — do not write!

• lowest possible number

to name compounds w/ a phenol or one other substituent: the parent is ___ and we assign the C attached to ___ as C1. 

• phenol

• —OH

to name compounds w/ a phenol or one other substituent: number the Cs in the ring so that the substituent ___.

get the smallest number.

to name compounds w/ a phenol or one other substituent: sometimes ___, ___, and ___ are used instead of numbers

o, m, and p

naming alcohols as substituent: named as a substituent when other functional group w/ a ___ is present.

higher ranking (such as aldehyde)

naming alcohols as substituent: as a substituent, the prefix for alcohol is ___.

“hydroxy”

lower rankings below alcohols are ___, ___, and ___.

alkyl groups, alkanes/ynes, and halogens

common names for methanol

methyl alcohol or wood alcohol

uses of methanol

antifreeze, solvent, fuel, and to denature ethanol

what does denaturing ethanol do

makes it undrinkable

how is methanol toxic

it is not directly harmful, rather when it is metabolized in the body, it converts into toxic compounds (methanal and methanoic acid)

• 15 mL leads to blindness

• 30 mL leads to death

recognize this: CH3OH

methanol

recognize this: CH3CH2OH …or… C2H5OH …or… C2H6O

ethanol

commons names for ethanol

ethyl alcohol or grain alcohol

why is ethanol called grain alcohol

b/c it can be fermented from grains by a process called alcohol fermentation in yeast - it is present in all alcoholic beverages

industrial ethanol production via ___

• hydration of ethene in an addition rxn

• ethene + water → ethanol

ethanol is treated with denaturants ___ or ___ to make it unfit for human consumption

methanol or isopropanol

industrial purpose of ethanol vs. beverage purpose of ethanol

ethanol used in beverages is subject to taxes, but when used in industrial purposes (cleaning products, fuels, solvents), these taxes can be avoided by adding denaturants to make it undrinkable

recognize this: C3H8O

2-propanol

common names for 2-propanol

isopropanol, isopryl alcohol, or rubbing alcohol

uses of 2-propanol

common solvent, used to sterilize instruments, and as a skin cleanser before drawing blood or giving injections

hand sanitizer contains 70—80% of ___.

ethanol

ID this structure: common and IUPAC name

• common: ethylene glycol (EG)

• IUPAC: 1,2-ethanediol

ethylene glycol does NOT contain ___.

C=C

characteristics of ethylene glycol

• 2 —OH groups

• colorless liquid

• miscible w/ H2O

• sweet taste

• lethal to humans and dogs

common use of ethylene glycol

antifreeze

ID this structure: common and IUPAC name

• common: glycerol or glycerin

• IUPAC: 1,2,3-propanetriol

characteristics of glycerol 

• contains 3 Cs, each bound to an —OH group

• nontoxic liquid

• miscible w/ H2O

• forms structural backbone of fats and oils

common use of glycerol

used as moisturizer b/c —OH groups interact w/ H2O

ID this structure

triacylglycerol

ID this structure

serine

ID this structure

glucose

ID this structure

threonine

ID this structure

cholesterol

ID this structure

ribose

ID this structure

deoxyribose

2 kinds of alcohols

aliphatic and phenols

2 kinds of ethers

saturated (alkyl) and unsaturated (aryl)

ID this structure

ether

aryl group definition

• indicates aromatic functional group

• Ar—OH

ethers can be present in (attached to or integrated in) these four forms

linear, cyclic, ring, or benzene rings

ether common naming: the prefix “di—” is used if ___.

both the alkyl groups are the same

ether common naming: ID the ___ groups attached in the O atom

2 alkyl 

ether common naming: put the alkyl groups in ___ w/ spaces b/t the names and followed by the word ___.

• alphabetical order

• ether

ether IUPAC naming: ID ___ groups connected to O atom

alkane/alkyl

ether IUPAC naming: select the ___ alkyl group as the parent chain, and name it as an ___.

• longer (if there is one)

• alkane

ether IUPAC naming: name the shorter alkyl group and add the suffix ___ to indicate it is part of the ether

“—oxy”

ether IUPAC naming: number the C atoms in the parent chain to provide the lowest numbers for the ___.

O atom

ether IUPAC naming: ethers are typically names as ___ w/in a larger molecule(s)

substituents

ether IUPAC naming: the smaller, shorter alkyl group becomes the ___, and the larger alkyl group becomes the ___.

• alkoxy substituent

• alkane root name

ether IUPAC naming: in ROR’, R’ is larger than R and is named as ___.

alkoxyalkane

ether IUPAC naming: an —OR group is referred to as an ___.

alkoxy group

3 major types of intermolecular forces

1. London dispersion forces

2. Dipole-dipole

3. Hydrogen bonding

all molecules experience this force

london dispersion forces

london dispersion forces definition

at any given moment, there might be an unequal distribution of e- w/in a molecule, leading to a momentary polarity and then a temporary attractive force

LDFs strength

weak force

LDFs intensity influenced by what

size and structure of molecules

LDFs are the only intermolecular interactions for ___ molecules

nonpolar - i.e., hydrocarbons

larger the molecular weight and surface area, the ___ the forces, and ___ BP

• greater

• higher

BP ___ as alkanes increase in size

increase

branching ___ intermolecular interactions mainly b/c it ___ the surface area available for contact b/t molecules

• decreases

• decreases

BP ___ w/ ___ branching in isomers

• decreases

• increased

dipole-dipole forces definition

electrostatic attraction force b/t positive and negative ends of polar molecules

strength of dipole-dipole

stronger than LDFs and weaker than H-bonding