salicyl alcohol acetyl salicylic acid. saturated carbon chains c c-c c-c-c

Salicyl alcohol acetyl salicylic acid

Saturated carbon chains

C

C-C

C-C-C

CATENATION: OLD (CHEM 1):

Valence

IONIC COVALENT

CH3

morphine = Acylated morphine=Heroine

CH3

Name the following alkanes:

C2H6

C4H10

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned. Include specific examples.

Saturated carbon chains

ROOT NAME EXAMPLE

C

C-C

C-C-C

C-C-C-C

5 C

6 C

7-C

8 C

9 C

10 C

-OH is the alcohol functional group

Generic alcohol can be written R-OH

R, represents a carbon chain of some sort

There is an interesting legend surrounding the discovery of soap making. This legend accords the discovery of soap to the Romans so it must be a Roman legend to confront the Celtic claim to soap making. Probably both of these inventive peoples discovered soap making independently.

The legend says soap was first discovered by women washing clothes along the Tiber River at the bottom of Sapo Hill. The women noticed the clothes became cleaner with far less effort at that particular location. What was happening? The ashes and the grease of animals from the sacrificial fires of the temples situated on the top of Sapo Hill mixed with the rain, making soap which ran down the slope in the streams of rain water giving the women a wash day bonus.

You can see at a glance saponification, the chemical name for the soap making reaction, bears the name of that hill in Rome long ago, which caused one Roman washer women to comment to another, "My wash is cleaner than yours".

Organic compounds are those that are made mostly of carbon

Carbon chain molecules, with hydrogen filling up the extra bonding areas.

Can be one carbon, 2,3,….20… Non carbon parts are known as functional groups.

What are esters? Esters are derived

from carboxylic acids. A carboxylic acid contains the -COOH group, and in an ester the hydrogen in this group is replaced by a hydrocarbon group of some kind

Lipids are a group of water INSOLUBLE compounds that include Fats Oils Waxes

Your cells are made of a lipid bi-layer.

In a strong base or acid water , H-OH, willbreak apart the

R-COO-RInto

R-COOH and R-OH

Carboxylic Acid and Alcohol

Hydrolyzing fats in the presence of a base Like NaOH…sodium hydroxide.

Soaps are alkali metal salts (Na, K, or Li)of carboxylic “fatty” acids.When put into a NaCl mixture,

the soap separates from the glycerol

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned. Include specific examples.

Review the work from your notebook from the past week.

Spend 5 minutes writing/reflecting about what you learned.

Insoluble in water

~Apple wax C27H56

Broccoli C29

Tobacco C31

Low boiling points compared to similar weight molecules.

(only London/Van der Waal’s dispersion forces)

Branched alkanes have lower boiling points than straight.

More spherical molecules are more difficult to induce dispersion forces. (=weaker)

Pentane36

2-methyl butane 28 (isopentane)

2,2 dimethyl propane10

Petroleum-liquid mixture of

organic compounds: mostly alkanes and cycloalkanes.

From decayed animal and vegetable matter

Parts are separated by distillation

Natural Gas- Gas mixture of

methane (80%) and ethane (10%) and other alkanes

- Often found near deposits of petroleum

2- butene

2-3 dimethyl butane

Cis = same side

Cis 1,2 dimethlycyclopentane

Trans = opposite side

Oxidation of an alkane, replace C-H bond(s)with C-O

bond(s)

Alkanes used as fuels

Alkane + O2 CO2 + H2O - ∆H

heat energy released

Substitution reactions

A halogen replaces a hydrogen

R-H + Cl-Cl R-Cl + H-Cl

Chloroethene

(Vinyl chloride)

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Family of organic acids.Weak acids

Functional group COOH

or CO2H

Carbonyl C=O Hydroxyl -OH

A carboxylic acid derivative replaces the -OH (hydroxyl) group with another functional group.

Examples:• esters• acyl halides

Alkane = ethaneCarboxylic acid =

ethanoic acid

Replace the final e of the alkane with “–oic” add the word “acid”

Alkane = benzeneCarboxylic acid =Benzenoic acid(benzoic)

The hydroxyl group -OH of the carboxylic acid is replaced by

-OR’

R first-OR’ next. Change ”ic” to “ate”

Our favorite results so far:

Alcohol Carboxylic acid Name Odor

C8H8O2 COOH (Ester)

Alkanes, Alkanes, they're driving me insane.

1) pi bonds ( π ) are broken

( π )1) sigma bonds ( σ )

formed to 2 new atoms

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation

Br2 to an alkeneCl2 to an alkeneIThe addition of a single halogen to each

carbon of the double bond.

The reaction is spontaneous, occurs at room temperatures, and needs no additional energy input.

electrophilic addition

Reaction of :1-hexene with bromine.

Cyclopentene with bromine.

1) pi bonds ( π ) are broken

( π )1) sigma bonds ( σ )

formed to 2 new atoms

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation

Water H- OH adds to the double bond of an alkene.

An acid is required to act as a catalyst (H+)

ProblemAcid catalyzed hydration of

2-butene

Br2

H2O

H2

HBr

Problem:Hydration of 2-methyl-2-butene

Addition products of unsymmetric reagents to unsymmetric alkenes are called regioisomers.

REGIOSPECIFICREGIOSELECTIVE

Determines where an unsymmetrical reagent will react. Which regioisomer will be favored.

The electronegative part bonds to the carbon with the least number of hydrogens.

problems1-butene + HBrHydration of 1-chloro-2-butene (using an acid

catlalyst)

3.8 (pg 85)3.9 (pg 85)3.10 (pg 86)3.11 (pg 88)

look up the following terms:electrophile , nucleophile, and

carbocation.

Electrophile: E+

electron poor reactant; seeks electrons

Nucleophile: Nu-

electron rich reactant; forms bonds by donating electrons. (to electrophiles)

How many sigma bonds, and how many pi bonds are there?

In a multistep process, bromine is added to all the pi electrons.

First mole of Br2 produces a trans product.

Second mole of Br2 produces a fully halogenated procudt.

Ethyne (Acetylene)+ Br2

With a Ni or Pt catalyst

Alkynes are fully hydrogenated

C2H2 + H2

With palladium catalyst (Lindlar’s catalyst)

Only 1 mole of H2 is added and you end up with a cis alkene

Ni

CH3CCH + H-Br

Follow Markovinkov for each step.

3.40 a-f

3.42 a-e

3.53a

Alcohols ACETIC PROPIONOIC BENZOIC

SALICYLIC

Methyl

Ethyl

Propyl

Isoamyl

Octyl

Charcoal is used as a filtering material

The charcoal has a very large surface area per unit mass

1g has 500-1000m2 of reactive surface area

Has an affinity for organic compounds, gases, halogens.

Great to remove contaminants.

Charcoal filtration of Grape Juice.Sketch your lab set up, describe the

procedures, and results.

Molecules with empirical formula CH2O they are ‘hydrates’ of Carbon

Examples: glucose, fructose, dextrose Uses:

cell energy requirements cell structures

Monosaccharides (ex. Glucose) Simples carbohydrates Are the building blocks of other

carbohydrates Disaccharides

2 mono-sacs bonded together Polysaccharides

Large carbohydrates, polymers built of many monos

Aldehyde

Ketone

Aldose Ketose

Describe an isomer

Structrual = different bond pattern

Stereoisomers = same bond pattern

Two 3-d forms of a molecule with different orientations in space.

Stereoisomers are chiral. (Show handedness)

Try to superimpose your left and right hand.

Build chlro-bromo methanol. (use different color for the 2 halogens)

Determine if you have the R, or S version1. Locate the sterocenter.2. Assign priority based on molecular weight to each

attached atom.3. Orient the molecule so the lowest priority is

pointed away from you.4. Trace your finger in a circle beginning with the

highest priority to the lowest priority.5. IF the circle is clockwise, you have an R isomer. if the circle is counterclockwise you have an S

isomer.

The mirror image of a chiral molecule cannot be superimposed on the molecule itself.

(an achiral molecule can be superimposed)

Build the following molecule(s).

2- butanol2-propanol

Stereocenter is a carbon with 4 unique attachements.

Build/Draw 2 chlorobutane 3 chloro cyclohexene

Identify the stereocenter in each molecule

Stereoisomers have identical chemical and physical properties.

Stereoisomers are OPTICALLY active. Our enzymes typically only react with 1

of the 2 stereoisomers. The binding sites for enzymes are based on a specific chirality.