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HYDROCARBONS CHEMICAL TESTS ORGANIC DERIVATIVES OF WATER CARBONYL COMPOUNDS CARBOHYDRATES, Study notes of Organic Chemistry

University of the Philippines Diliman (UPD)Organic Chemistry

HYDROCARBONS CHEMICAL TESTS ORGANIC DERIVATIVES OF WATER CARBONYL COMPOUNDS CARBOHYDRATES

Typology: Study notes

2022/2023

Available from 08/06/2023

shei_hernan 🇵🇭

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HYDROCARBONS

- Compounds containing H and C atoms

Classification:

1. Alkane

○ Saturated hydrocarbons because the C atoms contain the maximum number of H

that can bond.

○ Only C-C and C-H single bond

○ Straight chain: CnH(2n+2)

○ Cycloalkane: CnH(2n)

○ No functional groups present

○ 1 sigma

○ e.g. butane

2. Alkene

○ C-C double bond functional group

○ CnH(2n)

○

○ 1 sigma (overlap of sp2 orbitals) and 1 pi (overlap of p orbitals)

○ e.g. ethylene

3. Alkyne

○ C-C triple bond

○ CnH(2n-2)

○

○ 1 sigma (overlap of sp orbitals) and 2 pi bonds (overlap of 2p orbitals)

○ e.g. norethindrone

4. Aromatic hydrocarbons

○ Alternating double and single bonds forming a ring

○ Alkylbenzene - alkyl group attached to a benzene ring

○ overlap of 6 adjacent p orbital creates 2 rings of electron density (above and

below the plane = electron rich)

○ e.g. benzene

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HYDROCARBONS

Compounds containing H and C atoms Classification: 1. Alkane ○ Saturated hydrocarbons because the C atoms contain the maximum number of H that can bond. ○ Only C-C and C-H single bond ○ Straight chain: CnH(2n+2) ○ Cycloalkane: CnH(2n) ○ No functional groups present ○ 1 sigma ○ e.g. butane 2. Alkene ○ C-C double bond functional group ○ CnH(2n) ○ ○ 1 sigma (overlap of sp2 orbitals) and 1 pi (overlap of p orbitals) ○ e.g. ethylene

Alkyne ○ C-C triple bond ○ CnH(2n-2) ○ ○ 1 sigma (overlap of sp orbitals) and 2 pi bonds (overlap of 2p orbitals) ○ e.g. norethindrone
Aromatic hydrocarbons ○ Alternating double and single bonds forming a ring ○ Alkylbenzene - alkyl group attached to a benzene ring ○ overlap of 6 adjacent p orbital creates 2 rings of electron density (above and below the plane = electron rich) ○ e.g. benzene

CHEMICAL TESTS

** the only nonpolar solvent above is dichloromethane ● Hydrocarbons are soluble in dichloromethane but not in water because they are nonpolar (like dissolves like) ● Alkenes react with cold H2SO4 (Sulfonation) ● Reagent: Bromine in dichloromethane (red orange liquid) ● Positive: loss of red orange color ○ dichloromethane is a good solvent because it is nonpolar & inert towards hydrocarbon and bromine ● Free radical substitution ○ requires light ○ produce HBr as one of the products ■ How to test kung may HBr? Pag nag red ang blue litmus paper ○ Alkanes, alkylbenzene; toluene at faster rate

● Reagent: Ammoniacal AgNO ● Positive: formation of insoluble substance/gray precipitate ● Detects presence of terminal alkyne ● Acetylene reacts with reagent, forming silver acetylide + ammonia + ammoniacal ○ Only terminal alkynes can react with ammoniacal

ORGANIC DERIVATIVES OF WATER

compound containing C, H, O
replacement of H atoms of water by an organic group

Alcohol a. 1H replaced by alkyl b. Func group: hydroxyl group c. Primary (1R group), secondary, tertiary
Phenol a. 1H replaced by aryl b. hydroxyl group bonded to aromatic
Ether a. Both H replaced by alkyl or aryl

b. Inert molecules since stable ang C-O-C

CARBONYL COMPOUNDS

compounds with O
With carbonyl group:

Aldehyde - at least 1H attached to carbonyl
Ketone - 2 aryl/alkyl attached to carbonyl

Carbonyl group is polar; carbon bears positive charge ● Nucleophilic addition ○ Ketones < susceptible than Aldehyde because ○ Ketone > crowding than aldehyde ○ Non-stereospecific

CARBOHYDRATES

● polyhydroxy aldehyde/ketone ● according to: ○ carbon atoms (triose, tetrose … ) ○ kind of carbonyl group (aldose or ketose) ● Monosaccharide simplest unit of carbohydrate ● Intramolecular nucleophilic addition forms cyclic hemiacetal (pyranose-5; 6-furanose) ● Disaccharides 2 units ● Polysaccharides

Sucrose hydrolysed bc only 1 glycosidic linkage per molecule is broken. (disaccharide) Cellulose is not bc beta orientation of glycosidic bond is stable Starch hydrolysed bc alpha glycosidic bond is less stable

All monosaccharide + (glucose, fructose) due to aldehyde group for oxidation Lactose potential carbonyl group is not used/free in glycosidic bond Sucrose: both potential carbonyl groups are used in glycosidic bond

HYDROCARBONS CHEMICAL TESTS ORGANIC DERIVATIVES OF WATER CARBONYL COMPOUNDS CARBOHYDRATES, Study notes of Organic Chemistry

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HYDROCARBONS

CHEMICAL TESTS

ORGANIC DERIVATIVES OF WATER

CARBONYL COMPOUNDS

CARBOHYDRATES