Final Exam Chem 131

Green River. Final exam

Organic compound

\-always contains C and H sometimes N,O,P,S, or halogens

\-NO metal atoms, covalent bonds

\-low melting and boiling points

\-flammable

\-not soluble in eater if no polar (hydrophobic)

methyl

CH3-

ethyl

CH3-CH2-

propyl

CH3-CH2-CH2

isopropyl

CH3-CH2-CH3

|

butyl

CH3-CH2-CH2-CH2-

isobutyl

CH3-CH-CH2-

|

CH3

sec-butyl

CH3-CH-CH2-CH3

|

tert-butyl

CH3

|

CH2-C-CH3

|

fluoro

F-

chlorophyll

Cl-

bromo

Br-

iodo

I-Pre

prefixes

1 = mono-

2= di-

3= tri-

4= tetra-

5= penta-

6= hexa-

7= hepta-

8= octa

9= nona-

10= deca-

methane

CH4

Ethane

CH3-CH3

Propane

CH3-CH2-CH3

Butane

CH3-CH2-CH2-CH3

Pentane

CH3-CH2-CH2-CH2-CH3

Hexane

CH3-CH2-CH2-CH2-CH2-CH3

Heptane

CH3-CH2-CH2-CH2-CH2-CH2-CH3

Octane

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3

Nonane

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

Decane

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

IUPAC name with cycloalkanes

\-no number for single alkyl group or halogen atoms

IUPAC name with alikanes and substituents

\-muliple sub of same name use greek prefix (never mono)

Alkanes

\-lowest melitng/boiling point, weak disperson forces

\-Branched alkanes lower boiling point than straight-chain isomer

\-longer chain more disperson force (more carbons)

\-CYCLOalkanes high boiling point than striaght-chain isomer

Alkenes and cycloalkenes

\-C=C bond

Alkynes ad cycloalkanes

* Triple bond carbon- carbon

cis-trans isomers

\-cis:larger groups on the same side of the double bond

\-trans:larger group on the opposite side of double bond

bonding benzenes

\-ring with 3 alternating double bonds

\-use circle in middle for drawing line angle and three lines for condensed structure

Aromatic Copounds

Step 1: write name for aromatic compound. aromatic base with one of the common names instead of benzene

Step 2: if tow or more substituents, give lowest values to substituends

Step 3: name each substituent include common and put in alphabetical order

Common name for alcohols

\-name of alkyl gorup follwed by alcohol( methyl alchohol,cyclohexyl alcohol)

common name for phenols

\-methylphenal is called cresol

alcohol, phenol, thiol draw-

\-alchohol has a-OH attacted to carbon

\-phenol has a-OH attached to benzene ring

\-thiol has a-SH attached to catbon

\-S or O always attached, never H

Common name for ethers

\-two alkyl or aromatic group written in alphabetical order

\-end name is ether

drawing ether

\-oxygen atom attached by two single bonds to two carbon groups

\-two carbon groups will alwys be alkyl group or aromatic group

Classification of alchohols

\

boiling point of alcohols and ethers

\-alcohol and ether boiling point increases as carbons are added

\-ether has lower boiling point thann alcohol becasue it doesn’t intiate hydrogen bonding

solubility of alcohols phenols and ethers

\-alcohols 1-3 carbons soluble in water 4 carbons slightly soluble

\-ethers 2-4 carbons slightly soluble in water 5 carbons insoluble

\-phenol slightly soluble in water

dehydration reaction for alcohol

\-alkene(2 double bonned c)+ water

\-loses -H and -OH from adjacent carbon atoms of the same alcohol

oxidation reaction for primary alcohol

\-primary oxidize to produce aldehyle (double doned c-c and h)

oxidation of secondary alcohol

\-secondary alcohols oxiixe to produce a ketone( double bonded c-c and c)

oxidation of tertiary alcohols

\-can’t oxide because there si no H on the a-carbon

Oxidation of aldehydes

\-aldehydes oxidize to produce carboxylic acid (H turns into OH)

catalyst for different reactions

\-oxidation \[O\]

\-reduction: pt, ni, or pd

\-dehydration: H+, heat

compounds with carbonyl groups as aldehydes and ketones

\-O=C

\-aldehyde is -CHO

\-ketoen is -CO-

common names for aldehydes and ketones

\-greek prefix -aldehyde (acetaldehyde)

\-1C= form-, 2C= acet, 3C= propion, 4C= butyr

\-alkyl group bonded to carbon group are listed alphabetically -ketone (ethyl methyl ketone)

boiling point and solubility of aldehydes and ketones

-boiling point increased as carbons increase

• 1-4 carbons soluble in water, 5 carbons slightly soluble, 6+ carbons insoluble

• -both accept hydrogen bonds, not initiate

formulas of aldehydes and ketones

\-condense as CHO or CO

reactants and products in oxidation /reduction reactions of aldehydes and ketones

\-aldehydes oxidize into carboxylic acid

\-ketones don’t oxidize because they don’t have a hydrogen

Oxidation of Aldehydes

\-aldehydes reduce into primary alcohols

\-ketones reduce into secondary alcohols

reduction of aldehydes and ketones

difference between tollen and benedict’s test

\-tollens oxidizes aldehydes and forms a silver mirror but not ketones (negative for ketones

\-benedict turns brick red when reacting with aldehyde

hemiacetals and acetals

\-meniacetals contain an -OH and -OR group on the same carbons atoms

\-acetals contain two -OR groups on the same carbons

monosaccharides as aldose or ketose

\-alsoses have a H-C+O (aldehyde) group at the top in the Fischer structures

\-ketoses have CH2OH-C=O (ketone) group at the top of fisher strctures

Number of carbons in monosaccharides

\-triose (3 carbons atoms)

\-tetrose (4 carbon atoms)

\-pentose (5 carbon atoms)

\-hexose (6 carbon atoms)

chiral and a-chiral in organic molecules

\-carbon atoms are chiral if they have four different atoms or groups

D or L enontiomers of monosaccharides with fisher projections

\-D= right Oh on the last chiral carbon

\-L= left HO on last chiral carbon

common monosaccharides based on thier structures and functions

\-D-glucose: blood sugar) aldohexose

\-D-galactose (found in milk) aldohexose

\-D-Fructose (fruit sugar) ketohexose

haworth stuctures for monosaccharides

\-turn figher projection 90 clockwise, bond O on carbon 5 to carbon 1, draw Oh on carbon 1 accround to the isomer

\-pentagon if fructose or ketohexose

\-a isomers hav -OH below carbon 1

\-B isomer have -Oh above carbon 1

oxidation or reduction of monosaccharides

\-oxidation converts top form H-C+O to HO-C=o

\-oxidation renames -ose ending to -onic acid

\-reduction converts top from H-C-O to CH2OH

\-reduction renames -ose ending to -itol

carbohydrate is a reducing sugar

\-all aldoses are reducing sufars that can oxidize to carboxylic acids

\-all ketoses are reducting sufars due to rearrangement

monosaccharides in disaccharides

\-glucose+glucose = maltose

\-a-1,4 glycosidic bond

\-glucose_galatose = lactose

\-B-1,4 glycosidic bond

\-glucose+fructose = sucrose

\-a,B- 1,2 glycosidic bonds

Amylose

\-20% of starch: storage form of glucose in plants

\-glucose molecules connected by a-1,4 glycosidic bonds

Amylopectin

\-80% of starch

\-glucose molecules connected by a-1,4 and a-1,6 glycosidic bonds

Glycogen

\-glucose stored in liver and muscle to provide energy between meals

\-glucose molecules connected by a-1,4 glycosidic bonds with branches attached by a-1,6 glycosidic bonds

\-like amylopectin but more highly branched

Cellulose

\-structural unit of woods and plants

\-unbranched chain of B-1.4 glycosidic bonds

\-can’t be digested by humans

carboxylic acid

\-prefix for carbon is ic acid

\-substituted carboxylic acids, the carbon next to COOH is called a and followed by B, y, and delta

draw corboxylic acid

\-carboxylic acid contains a carboxyl grou consists fo hydroxyl group (-OH) attached to the carbon in carbonyl group (C=O)

\-con carbon in carboxyl group as first carbon

Boiling points and solubility of carboxylic acids

\-polar carboxyl group allows carboxylic acid to form multiple hydrogen bonds with carboxylic acids wihc gives the carboxylic acid a higher boiling point than alcohols,ketones, and aldehydes of similar molar mass

\-carboxylic acids with 1-5 carbon atoms are very soluanlt n water, 6+ are slightly soluble

Neutralization reactions of carboxylic acids

\-carboxylate salts are a products of neautralization of carboxylic acids with strong base like NaOH or KOH

\-carboxylate ion is named by replacing ic acid ending with ate

Esterfication

\-equalibrium reaction of a carbocylic avid and alcohol in the presence of an acid catalyst and heat to produce an ester

common names for esters

\-first word indicated alkyl part from alcohol

\-sec word carboxylate from carboxylic acid

Ester structure

Products form base hydrolysis of esters

\-ester reaction with strong base to produce carboxylate salt and alcohol

\-heat requried

Boling point and solubility of esters

\-boiling point higher than alkanes and ethers, lower than alcohols and carboxylic acids

\-ester don’t have hydroxyl groups so they can’t hydrogen bond to each other

\-esters with 2-5 carbons are soluble

Summary of reactions

lipids

\-steriods

\-fatty acids

fatty acids

\-long unbranched carbon chains with a carboxylic acid group at the end.

\-insoluble in water becasue of long chain

Fatty acids as saturated or unsaturated

\-saturated when theyhave single c-c bond in carbon chain

\-unsaturated when they have c=c bond in carbon chain

wax produced by reaction of fatty acid and alcohol or glycerol

\-wax is a ester of long chain fatty acid and alcohol, with 14-30 carbon atoms

triacylglycerol produced by reaction of fatty acid and alcohol or glycerol

triaclyglycerols are ester of fatty acids and glycerol

Triacylglycerol that undergoes hydrogenation

\-Double bonds in unstaruated fatty acids react with hydrogen gas to produce c-c bond

Triacylglycerol that undergoes hydrolysis

\-triacylglycerols are hydrolyzed (split by water) to produce glycerol and 3 fatty acids in presence of strong acids

Triacylglycerol that undergoes saponification

\-A fat and strong base react to produce glycerol and the soaps in presence of heat

Glycerophospholipids

\-Glycerol 2fatty acids, phosphoric acid and amino alcohol

Sphingomyelin

sphingosine, fatty acid, phosphate, amino acid

\*Amino Alcohols in glycerophospholipids are choline, serine, and ethanol amine

Steriod Nucleus

\-3 cyclohexane rings and 1 cyclopentane ring fused together

steriod compounds

\-cholesterol: synthesized in liver needed to make brain and nerve tussue, steriod hormones, vitamin D, bile salts

\-bile salts: emulsify fat globules, allowing fat to easily digester, synthesized in liver, sotred in gallbladder, help absorb cholesterol

\-steroid hormones: aldosterone and cortisone, regulate water balance and glucose levels in cells

Lipoprotiens

• surround nonpolar lipids with polr lipids and protiedn for transport to cells

• primary function to transport triglycerides and cholesterol around the body

• LDL bad lipoprotien transports cholesterol to make cell membranes and deposits excess into arteries

• HDL good lipoprotein transprots cholesterol from tissues to liver to make bile salts that can be eliminated

Lipid bilayer

\-cell membranes separate cellular contents from the external environment, consists of 2 rows of phospholipids

\-barrier to molecules passing in and out of cell

\-one layer facing out and other facing in so polar on the outside and nonpolar on the inside

Transprot through cell membranes

\-diffusion: moves particles from higher to lower concentration

\-Facilitated transport: uses protein channels to increase the rate of diffusion

\-active transport: move ions against a concentration gradient

Amines

\-alkyl groups not branched

\-alkyl groups banded to the N atom in alphabetical order in front of amine

\-prefixes di- and tri- to identify duplicate alkyl substituents

\-amine benzene is named aniline by IUPAC

Draw amines

\-shows amine molecules with alkyl groups bonded to nitrogen atom

Amines as primary secondary or tertiary

\-primary 1 carbon group bonded to nitrogen

\-secondary 2 carbon groups bonded to nitrogen

\-tertiary 3 carbon groups bonded to nitrogen

boiling points and solubility of amines

\-boiling point is higher than alkanes but lower than alcohols

\-primanry amines have higher boiling points than secondary amines becasuse they can form more hydrogen bonds

\-tertiary amines have lower boiling points than primary and secondary amines becasue they can’t form hydrogen bonds with each other

\-amines with 1-6 carbon atoms are soluble in water

reaction of amines with acids

\-amine + acid = ammonium salt

Heterocyclic amines

\-simplest 5 atoms ring is pyrrolidine

\-imines have double bonded nitrogens

\-amines have single bonded nitrogen

\-6atom ring purine is a combination of pyrimidine and imidazole

exciatory and inhibitoy neurotransmitters

\-excitatory increase the signal of activity in nerve cells

\-inhibitory decrease the signal of activity in nerve cells