Final exam orgo chem definitions

isomer

same molecular formula but different arrangement of atoms

stereoisomer

isomer that have same structural formula and bonding pattern, but dfferent 3D shape

hydrocarbon

molecule that contain only carbon and hydrogen

saturated

only C-C and C-H single bonds

unsaturated

contains double or triple bonds (C=C)

organic properties

covalent bond

intermolecular forces broken easily

not soluble in water

inorganic

ionic bonds

soluble in water

high MP and high BP

Ionic

electrons transfer from 1 atom to another

non-polar covalent

equal sharing of electrons

polar covalent

unequal sharing of electrons

alkene properties

CnH2n

rigid and flat

cis and trans

unsaturated hydrocarbon

alkyne properites

CnH2n-2

rigid and linear

unsaturated hydrocarbon

physical properties of both alkenes and alkynes

non-polar

not soluble

low melting/boiling point

highly soluble

saturated fats

animal fats

typically, solid at room temp

no double bonds

unsaturated fats

vegetable oils

typically, liquid at room temp

double bonds

trans-fatty acids

not naturally occurring

parsalmide

beneficial alkyne: pain reliever and anti-inflammatory properties

ethinylestradiol

beneficial alkyne: synthetic estrogen, in oral contraceptive

pargyline

beneficial alkyne: antihypertensive

capillin

toxic alkyne: wormwood plant → antifungal, may help plant survive

Ichthyothereol

toxic alkyne: plants and flowers →Latin American Natives used on fishing tips (helps kill fish)

cicutoxin

toxic alkyne: water hemlock (parsley/carrot family) → North American, is a neurotoxin; deadly if ingested

Markovnikov’s rule

the carbon of C=C that originally had more hydrogen atoms receives the new hydrogen atom (for hydration and hydrohalogenation rxns)

polymer

macromaolecules of repeating units called monomers

styrene

polymer of alkene: styrofoam containers

acrylonitrile

polymer of alkene: clothing

methyl methacrylate

polymer of alkene: basketball backboards

vinyl chloride

polymer of alkene: plastic pipe, credit cards

tetrafluoroethene

nonstick surfaces

ortho (o)

1,2 on ring

meta (m)

1,3 on ring

para (p)

1,4 on ring

Polynuclear aromatic Hydrocarbons and why They’re important

(PAH) are composed of two or more aromatic rings joined together

\-many have been shown to cause cancer

\-benzopyrene is one of the most potent carcinogens known; in coal tar, cigarette smoke, forest fires

carbinol carbon

carbon bearing the hydroxyl group

\-primary: attached to 1C

\-seconday: attached to 2 C

\-tertiary: attached to 3 C

alcohols MP and solubility

hydrogen bonds can form readily (intermolecular force)

\-more soluble in water

\-h-bonding increases attraction between molecules in solution resulting in higher MP

Naming alcohol

replace -e of the alkane name with -ol

\-if alcohol has multiple hydroxyls use diol and triol as a suffix--- 1,2-ethanediol

methanol

used as solvent

toxic, can cause blindness and death if ingested

can be used as fuel

ethanol

hand sanitizer

alcohol in alcoholic beverages

2-propanol (isopropyl alcohol)

rubbing alcohol

disinfectant

astringent

industrial solvent

1,2 ethanediol

automobile antifreeze

sweet taste, but is extremely poisonous

added to water

\-lowers the freezing point

\-raises the boiling point

zaitsev’s rule

in an elimination reaction, the alkene with the greatest number of alkyl groups on the double bonded carbon is the major product of the reaction

phenols

compounds in which the hydroxyl group is attached to a benzene ring

formula: Ar-OH

germicides

phenol in healthcare

agent that kills microorganisms

capsaicin

phenol food

riot control sprays

sensory nerve cells

chili peppers

gingerol

phenol in food

from ginger, gives it the “bite” flavor

resveratrol

phenol in food

green tea, chocolate, and red wine

antioxidant, anti-inflammatory, and anticarcinogenic

ether properties

more soluble-- O2 can H-bond to water

extremely volatile (evaporates easily)

highly flammable=easily oxidized in air

naming of ether

parent chain is based off of longest chain

the shorter alkoxy substituent

replace -ane with -oxy

reaction of ether

not reactive but flammable

Diethyl ether

ETHER-- anesthetic, very flammable

halogenated

ETHER- less side effects and safer- Desflurane, sevoflurane, isoflurane

Do thiols smell nice or smelly?

Which functional group is smelly?

Geraniol

scent in geraniums; in natural insect repellents

D-Limonene

oil from rind of citrus fruits; flavor/fragrance extract, cleaning products, solvent

Mycrene

from bayberry; spicy scent in perfume and candles

Farnesol

from roses, orange blossom, Lilly of the valley; skin care, may fight wrinkles and increase skin elasticity

retinol

form of vitamin A, penetrates outer layers of skin to stimulate formation of collagen and elastin, acne treatment

parsalmide

pain reliever and anti-inflammatory properties

ethinylestradiol

synthetic estrogen, in oral contraceptive

pargyline

antihypertensive

capilin

wormwood plant, anti-fungal, may help plant survive

Ichthyothereol

plants and flowers, Latin American Natives used on fishing tips

cicutoxin

Water Hemlock (parsley/carrot family), North America, is a neurotoxin; deadly if ingested

methanal

formaldehyde, AQ embalming fluid

ethanal

produced in liver, hangovers

benzaldehyde

almonds

propanone

nail polish and remover, solvents, paints, etc

low molar mass carboxylic acid

sharp, sour, unpleasant aromas

high molar mass carboxylic acid

fatty acids important in biochemistry

lactones

cyclic esters

Do esters smell nice or smelly

What functional group smells nice?

how to name esters

\-oic acid to -oate

how to name ketones

\-e to -one

how to name aldehyde

\-e to -al

Acid Chlorides and how to name them(draw them out later chpt 14)

noxious and an irritant

same BP as aldehydes and ketones

\-oic acid to -oyl

VIOLENT

acid anhydrides(draw them out later chp 14)

Super reactive

phosphoesters(draw out later chpt 14)

first stage breakdown in glycolysis- glucose to glucose-6-phosphate

phosphoanhydride(draw out later chpt 14)

like an organic acid anhydride but based on phosphorous

common in biological systems

Acetyl CoA

the main function is to deliver the acetyl group to the citric acid cycle to be oxidized for energy production

smell of an Amine?

very pungent smell (rotting fish) is from which functional group?

amphetamines

medically important Amines

elevate blood pressure and pulse; decrease fatigue

analegsics

medically important amines

pan relievers/painkillers

anesthetics

medically important amines

pain blockers, cause lack of sensation

opioid

medically important amines

2 types: oxycodone(the baine) and hydrocodone(the codeine)

decongestants

medically important amines

ephedrine

alkaloids

heterocyclic amine

cocaine, morphine, codeine, heroin, nicotine, quinine, LSD, caffeine

barbiturates

medically important amides- “downers”

acetaminophen

medically important amide- tylenol(relieves pain and reduces fever--NOT an anti-inflammatory drug)

Dopmaine

catecholamines (neurotransmitter), critical for good health

epinephrine

catecholamines (neurotransmitter), stimulates glycogen breakdown to get glucose ADRENALINE

which two neurotransmitters (catecholamines) do the “fight or flight” response

epinephrine and norepinephrine

norepinephrine

catecholamines (neurotransmitter) stimulates other glands and CNS and constricts blood vessels

histamine

neurotransmitter

vasodilator, stimulates secretion of stomach acid which can result in chronic heartburn

acetylcholine

neurotransmitter

nerve to muscle transmitter

nicotine

succinylcholine

constitutional isomer

structural isomer (atoms are attached in a completely different arrangement)

Achiral

no stereogenic centers(no chiral centers)-- an example is cis/trans

enantiomers

mirror image isomers (all chiral carbons change)

diastereomers

non-mirror image isomer (not all chiral carbons change)

Fischer projection lines

horizontal lines- projecting out of page

vertical lines- projecting into page

meso compound

one whose molecules are superimposable on their mirror images even though they contain chiral centers