esterification & dehydration

how is cyclohexanol converted to cyclohexene

dehydration where H2O is removed from the compound

dehydration experiment is an example of

an acid-catalyzed dehydration reaction and proceeds via an E1 elimination mechanism

purpose of strong acid in dehydration

cyclohexanol contains a secondary hydroxyl group which is not a good leaving group. exposure to strong acid leads to protonation of the alcohol which makes it a good leaving group

purpose of base in the reaction medium

deprotonates a hydrogen atom adjacent to the C-O bond, which forms a c-c pi bond and displaces the leaving group, producing the dehydrated product.

cyclohexene color and odor

colorless, sweet

cyclohexene fire

severe

cyclohexene inhalation

irritation, cns depression, ha, dizziness, drowsiness, labored breathing, kidney/liver damage

cyclohexene skin

defatting of the skin, redness, burning sensation

cyclohexene eyes

redness and irritation

cyclohexene ingestion

nausea, labored breathing, cns involvement, pulmonary aspiration, pneumonia

cyclohexene carcinogenicity

not a known carcinogen

cyclohexene mutagenicity

not a known mutagen

cyclohexanol color and odor

colorless, pungent

cyclohexanol fire

moderate

cyclohexanol inhalation

irritation, cns depression, dizziness, drowsiness, ha, nausea, vomiting

cyclohexanol skin

irritation, defatting of the skin, absorption may head to cns depression, headache, dizziness, drowsiness, nausea, vomiting

cyclohexanol eyes

irritation, redness, pain

cyclohexanol ingestion

irritation, coughing, abdominal pain, diarrhea, cns depression, ha, weakness, dizziness, drowsiness, nausea, and vomiting

cyclohexanol carcinogenicity

not a known carcinogen

cyclohexanol mutagenicity

possible mutagen

dichloromethane color and odor

colorless, sweet

dichloromethane fire

slight

dichloromethane inhlataion

irritation, lightheadedness, dizziness, tingling, numbness of the extremities, sensation of heat, sensation of fullness in the head, drunkenness mental confusion, nausea, headache, fatigue

dichloromethane skin

irritation, possibly burns, skin absorption may occur causing effects similar to inhalation

dichloromethane eye

pain, extreme irritation

dichloromethane ingestion

rapid, then slowed respiration, GI ulceration and hemorrhage, unconsciousness, cns depression, liver & kidney damage

dichloromethane carcinogen

known carcinogen

dichloromethane mutagenicity

possible mutagen

bromine color and odor

brown to red, irritating

bromine fire

negligible

bromine inhlation

irritation, copious mucous secreation, coughing, nosebleeds, headache, delayed nausea, diarrhea/abdominal pains, pulmonary edema, pneumonitis/pneumonia

bromine skin

cooling sensation, burning sensation, redness, pain, brown discoloration, blisters, discharging pustules, destructive burns and deep-seated ulcers

bromine eyes

redness, pain, blurred vision, burns, lacrimation, photophobia, loss of vision

bromine ingestion

burns of the mouth, throat, and stomach, brown discoloration and corrosion of the tounge and mucous membranes, sore throat, vomiting

bromine carcinogenicity

not a known carcinogen

bromine mutagenicity

not a known mutagen

potassium carbonate color and odor

colorless/white, no odor

potassium carbonate fire

negligible fire hazard

potassium carbonate inhalation

irritation, coughing, choking, pain, burns of the mucous membranes, pulmonary edema

potassium carbonate skin

severe pain, burns, brownish stains

potassium carbonate eyes

pain, burns, edema, corneal opacification, permanent opacity, blindness

potassium carbonate ingestion

immediate pain, corrosion of the mucous membranes, SOB, laryngitis, headache, nausea, vomiting, profuse salivation, difficulty or inability to swallow or speak

potassium carbonate carcinogenicity

not a known carcinogen

potassium carbonate mutagenicity

not a known mutagen

sulfuric acid solutions color and odor

colorless, no odor

sulfuric acid solutions fire

negligible

sulfuric acid solutions inhalation

irritation, shallowed/more rapid breathing, sneezing, burning/tickling sensation in the nose, throat, cough

sulfuric acid solutions skin

second and third degree skin burns, necrosis, charring, shock

sulfuric acid solutions eye contact

burning or stinging sensation, lacrimation, blurred vision, conjunctival congestion

sulfuric acid solutions ingestion

burning pain in the mouth, throat esophagus and abdomen, nausea, vomiting

sulfuric acid solutions carcinogenicity

known carcinogen

sulfuric acid solutions mutagenicity

not a known mutagen

Fischer esterification

reaction that converts a carboxylic acid into an ester. the -OH portion of the carboxylic acid is replaced by an -OR group from an alcohol.

water in esterification

The byproduct of this reaction is water, but since water is also a nucleophile, it can add back into the compound and hydrolyze the newly formed ester to regenerate the starting carboxylic acid

how do we circumvent reversibility

running the reaction in excess alcohol to drive the reaction towards the product

methanol color and odor

colorless and alcohollike

methanol fire

severe

methanol inhalation

irritation, coughing, unsteady gait, twitching, constipation, numbness and shooting pains in hands and forearms

methanol skin

irritation, skin absorption may lead to metabolic acidosis and effects on the eyes and cns given in acute ingestion

methanol eye

irritation, violent inflammation of the conjunctiva, and epithelial defects on the cornea

methanol ingestion

inebriation, drowsiness, coughing, headache, dullness, weakness, vertigo, dizziness, nausea, vomiting, occasional diarrhea, blindness

methanol carcinogenicity

not a known carcinogen

methanol mutagenicity

possible mutagen

methyl benzoate color and odor

colorless, fruity

methyl benzoate fire

moderate

methyl benzoate inhalation

irritation, sore throat, coughing

methyl benzoate skin

irritation

methyl benzoate eyes

redness, pain, irritation

methyl benzoate ingestion

abdominal pain, vomiting, diarrhea, depression

methyl benzoate carcinogenicity

not a known carcinogen

methyl benzoate mutagenicity

not a known mutagen

benzoic acid color and odor

white, varying sharp

benzoic acid fire

slight

benzoic acid inhalation

irritation, sore throat, coughing

benzoic acid skin

irritation, redness

benzoic acid eye

irritation, redness

benzoic acid ingestion

sore throat, gastric pain, nausea, vomiting, allergic reactions

benzoic acid carcinogenicity

not a known carcinogen

benzoic acid mutagenicity

not a known mutagen

sodium sulfate color and odor

white, odorless

sodium sulfate fire

negligible

sodium sulfate inhlation

irritation

sodium sulfate skin

irritation

sodium sulfate eye

irritation

sodium sulfate ingestion

diarrhea, fluid loss, blood in stools, hypotension

sodium sulfate carcinogen

known carcinogen

sodium sulfate mutageniciy

known mutagen

NaCl color and odor

colorless to white, no odor

NaCl fire

negligible

NaCl inhalation

coughing, dryness, sore throat

NaCl skin

irritation

NaCl eye

redness, pain, irritation and a stinging sensatioin

NaCl ingestion

dryness of mucous mebranes, violent inflammatory reaction of gi tract, ulceration in large dose

NaCl carcinogenicity

not a known carcinogen

NaCl mutagenicity

not a known mutagen

sodium carbonate color and odor

colorless to white, odorless

sodium carbonate fire

negligible

sodium carbonate inhalation

irritation, coughing, sob

sodium carbonate skin

irritation, redness

sodium carbonate eyes

severe irritation, redness, pain, and blurred vision