17.6 Alcoholic Reactions (2023)

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    After completing this section, you should be able to:

    1. Discuss the reactions of alcohols presented in the previous units. These reactions include:
      1. Alcohols are converted to haloalkanes.
      2. Alcohols are converted to tosylate.
      3. Dehydration of alcohols to alkenes.
      4. Alcohols are converted to esters.
    study notes

    As you read Section 17.6, you should be ready to review some of the alcohol reactions discussed above:

    • Dehydration to alkenes – Section 8.1.
    • Conversion to haloalkanes - Section 10.5.

    You might also want to read the discussion of the acid constant, found in Section 2.8.

    Remember that when alcohol reacts with tosyl chloride to form tosylate, the O‡H bonds in the alcohol are destroyed, not the C‡O bonds. This means that the absolute configuration of the carbon atom attached to the hydroxyl group remains unchanged during the reaction. Read on to illustrate how this fact can be used to control stereochemistry in organic synthesis.

    Finally, the screen showed the formation of esters from alcohols and acid chlorides. In Section 21.3, we discussed the Fischer esterification reaction, a well-known reaction that uses alcohols and carboxylic acids to form esters.

    Conversion of alcohols to alkyl halides

    When alcohols react with hydrogen halides, substitution occurs to form haloalkanes and water:

    17.6 Alcoholic Reactions (1)

    • The order of reactivity of alcohols is 3° > 2° > 1° methyl.
    • The order of reactivity for hydrogen halides is HI > HBr > HCl (HF is generally unreactive).

    The reaction is catalyzed by acid. Alcohols react with the strongly acidic hydrogen halides HCl, HBr, and HI, but not with the nonacids NaCl, NaBr, or NaI. Primary and secondary alcohols can be converted to alkyl chlorides and bromides by reaction with a mixture of sodium halide and sulfuric acid:

    17.6 Alcoholic Reactions (2)

    Reaction mechanism of alcohols with HX

    Secondary, tertiary, allylic, and benzylic alcohols appear to react through a mechanism involving the formation of carbocations, with protonated alcohols serving as substrates in the \(S_N1\) reactions.

    The \(S_N1\) mechanism is illustrated by the reaction of tert-butanol and aqueous hydrochloric acid (\(H_3O^+\), \(Cl^-\) ) . The first two steps of this substitution mechanism \(S_n1\) are the protonation of the alcohol to form the oxonium ion. Although the oxonium ion arises from the protonation of an alcohol, it can also be seen as a Lewis acid-base complex between the cation (\(R^+\)) ​​and \(H_2O\). Protonation of the alcohol converts a bad leaving group (OH-) to a good leaving group (\)H_2O\_), which makes the dissociation step of the \(S_N1\) mechanism more favourable.

    17.6 Alcoholic Reactions (3)

    In step 3, the carbocation reacts with a nucleophile (halide ion) to complete the substitution.

    (Video) Organic chemistry (II) 232 CH 17.6: Reactions of alcohols, conversion of alcohol to alkyl halide

    17.6 Alcoholic Reactions (4)

    When we convert an alcohol to an alkyl halide, we are carrying out the reaction in the presence of an acid and a halide ion, not at a high temperature. Halide ions are good nucleophiles (they are much stronger nucleophiles than water) and because halide ions are present in high concentrations, most of the carbocations react with lone pairs of halide ions to form one more species. stable, the alkyl halide product. The overall result is a response \(S_n1\).

    Not all acid-catalyzed conversions of alcohols to alkyl halides result from the formation of carbocations.Under acidic conditions, primary alcohols and methanol react via S to form haloalkanes.NO2 mechanisms.

    In these reactions, the job of the acid is to produceprotonated alcohol.so the halide ion displaces a water molecule (a good leaving group) from carbon, creating an alkyl halide:

    17.6 Alcoholic Reactions (5)

    Acid is also needed here. Although halide ions (particularly iodide and bromide ions) are strong nucleophiles, they alone are not sufficient for substitution reactions with alcohols.There is no direct displacement of the hydroxyl group since the leaving group must be a strongly basic hydroxide ion:

    17.6 Alcoholic Reactions (6)

    Now we can understand why the acid promotes the reaction of alcohols with hydrogen halides.

    Carbocation rearrangements are extremely common in organic chemical reactions and are defined as the movement of carbocations from an unstable state to a more stable state through a "transition" using various structural rearrangements within the molecule. Once the carbocation is transferred to another carbon, we can say that there are structural isomers of the original molecule. However, this phenomenon is not as simple as it seems.

    mostcommon methodTo convert 1st and 2nd alcohols to the corresponding chloro and bromo alkanes (THAT IS TO SAY.exchange of hydroxyl groups) were treated with thionyl chloride and phosphorus tribromide, respectively. Due to the strong acidity of these hydrohalic acids andcarbocation rearrangementin connection with its use.

    Several options are available to synthetic organic chemists looking to convert alcohols into better leaving groups. A common strategy is to use thionyl chloride or phosphorus tribromide to convert the alcohol to an alkyl chloride or bromide:

    17.6 Alcoholic Reactions (7)

    17.6 Alcoholic Reactions (8)

    Despite their general utility, phosphorus tribromide and thionyl chloride also have drawbacks. The 1st and 2nd hindered alcohols react slowly with the former and can form rearrangement products as shown in the formula below.

    17.6 Alcoholic Reactions (9)

    A simplified reaction mechanism is shown below. If the HBr by-product is removed by the base, the initially formed trialkyl phosphite can be isolated. A series of acid-base compounds and S in the presence of HBrNOTwo reactions take place with the simultaneous transient formation of the intermediate carbocation. Rearrangement of carbocations (pink arrows) leads to isomeric products.

    17.6 Alcoholic Reactions (10)

    Inversion or retention has been observed in the reaction of thionyl chloride with 2° chiral alcohols. In the presence of a base such as pyridine, the chlorosulfite intermediate reacts to form a "pyridinium" salt, which undergoes a relatively clean S. reaction.NO2 The reaction is chloride inverted. In diethyl ether and similar solvents, chlorosulfite reacts and maintains its configuration, probably through close or close ion pairs. This is classified askleinNOIReaction (internal nucleophilic substitution). Carbocation partners in ion pairs can also rearrange. These reactions are illustrated by the following equations. An alternative explanation for the retained configuration is based on the initial molecular displacement of the chlorosulfite group by the solvent (eg SO).2and chloride ions) followed by displacement of chloride ions from the solvent fraction. In this case, two investments lead to retention.

    Example 17.6.1: Conversion of alcohols to alkyl chlorides

    17.6 Alcoholic Reactions (11)

    One important thing to note here: Do you see the stereochemistry? It's the other way around. *(White lie alert - see below) This is an important difference between \(SOCl_2\) and TsCl, leaving only the stereochemistry. We'll talk about the actual cause later, but in the meantime, can you think of a mechanism that would cause the carbon structure to reverse?

    (Video) Organic chemistry (II) 232 CH 17.6 Reactions of alcohols: Dehydration of Alcohols


    Since the reaction proceeds via a backside attack (\(S_N2\)), the carbon configuration is reversed

    17.6 Alcoholic Reactions (12)

    The mechanism for the formation of acid chlorides from carboxylic acids is similar. The process of converting carboxylic acid to acid chloride is similar, but the [1,2] chloride ion is added to the carbonyl carbon followed by [1,2] elimination to give the acid chloride \(SO_2\) \(hydrochloric acid \ )

    PBR3The reaction is assumed to involve two consecutive SNOSteps like 2:

    17.6 Alcoholic Reactions (13)

    Note that these reactions result in the reversal of the stereochemistry of the resulting alkyl halides.

    Conversion of alcohol to tosylate

    Alternatively, we can convert an alcohol group to a sulfonate usingfor-Toluenesulfonyl chloride (Ts-Cl) or methanesulfonyl chloride (Ms-Cl), giving rise to the so-called organic compoundstosilatooApiary:

    17.6 Alcoholic Reactions (14)

    17.6 Alcoholic Reactions (15)

    You also have an opportunity to examine the mechanisms of tosylate and mesylate formation in a problem statement in Chapter 12. Note, however, that unlike previous halogenation reactions, the electrophilic carbon configuration is preserved when the alcohols are converted to tosylate or mesylate.

    Chloride, bromide, and tosylate/mesylate groups are excellent leaving groups in nucleophilic substitution reactions due to resonance delocalization that forms a negative charge on the leaving oxygen.

    17.6 Alcoholic Reactions (16)

    The laboratory synthesis of isopentenyl diphosphate, the "building block" molecule used in nature to build isoprenoid molecules such as cholesterol and beta-carotene, was achieved by first converting the alcohol to an organic tosylate (step 1) and then converting the tosylate replaced with this Complete the nucleophilic group with the inorganic pyrophosphate (step 2) (Chemical J. Organization 1986,51, 4768).

    17.6 Alcoholic Reactions (17)

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    Example 17.6.2

    Predict the structures of A and B in the following reactions:

    17.6 Alcoholic Reactions (18)

    The importance of sulfonic acid esters as intermediates in many substitution reactions cannot be overstated. A rigorous test of configuration inversion occurring at the substitution site in SNO2 reaction uses such a reaction. An example of such a test is shown below.

    reverse test

    17.6 Alcoholic Reactions (19)

    Dehydration of alcohols to alkenes.

    a synthetic methodas an olefinIt is the process by which alcohol loses water and forms a double bond through the dehydration of the alcohol through the E1 or E2 mechanism. A dehydration reaction of the alcohol occurs.as an olefinThis is done by heating the alcohol to high temperatures in the presence of a strong acid such as sulfuric or phosphoric acid.

    17.6 Alcoholic Reactions (20)

    The required reaction temperature range decreases as the degree of substitution increases.hydroxylCoal:

    • Alcohol 1°: 170° - 180°C
    • Alcohol 2°: 100° – 140°C
    • 3° Alcohol: 25° – 80°C

    If the reaction does not get hot enough, the alcohol will not dehydrate and formas an olefin, but react with each other to form ethers (for example, Williamson ether synthesis).

    17.6 Alcoholic Reactions (21)

    alcohol isZwitter; They can act as both acids and bases. The lone pair of electrons on the oxygen atom makes the -OH group weakly basic. Oxygen can donate two electrons to an electron-poor proton. Therefore, in the presence of a strong acid, R-OH acts as a base.protonationvery angryalcoxinioIon+Oh2(HepKathe value of higher educationprotonatedThe alcohol content can be as low as -3.8. This fundamental property of alcohol is essential for the formation of its dehydration reaction with acid.as an olefin.

    17.6 Alcoholic Reactions (22)

    The mechanism of dehydration of alcohol.as an olefin

    Different types of alcohols can be dehydrated through slightly different mechanisms. However, the general idea behind any dehydration reaction is that the OH group in the alcohol donates two electrons to the H.+Formation occurs from acidic reagents.alcoxinioIon. This ion acts as a good leaving group and leaves the formedcarbocacion.HedeprotonatedSauernucleophile) then attack the neighboring hydrogencarbocacionand form double bonds.

    Primary alcohols undergo bimolecular elimination (E2 mechanism), while secondary and tertiary alcohols undergo bimolecular elimination.unimolecularelimination (E1 mechanism). The relative reactivity of the alcohols in the dehydration reaction is ordered as follows

    Methanol < primary < secondary < tertiary

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    Primary alcohols are dehydrated through the E2 mechanism. Oxygen loses two electrons from sulfuric acid H to a proton.2So4, forming onealcoxinioIon. Sonucleophile high sulfur content4Attack a neighboring hydrogen from behind andalcoxinioThe ions leave the system in a cooperative process and form a double bond.

    17.6 Alcoholic Reactions (23)

    Secondary and tertiary alcohols are dehydrated through the E1 mechanism. Similar to the previous reaction, secondary and tertiary OH are formed.protonationto formalcoxinioIon. In this case, however, the ions first leave the structure and formcarbocacionas a reaction intermediate. water molecules (ratiohigh sulfur content4-ion) then extracts a proton from the adjacent carbon, forming a double bond. Notice this in the following mechanismAsThe formation depends on which proton is removed: the red arrows indicate the formation of more substitutions2-buteno, while the blue arrows show the formation of less substituted substances1-buteno.Remember the general rule for more substitutionas an olefinReplace less, more stableas an olefin, Ytrans as an olefinComparecis as an olefin.For this reason, Hetrans diastereoisómeroVon2-butenoThe most common products

    Dehydration reactions of secondary alcohols.

    17.6 Alcoholic Reactions (24)

    The dehydration mechanism of tertiary alcohols is similar to that of secondary alcohols described above.

    Under relatively non-acidic conditions, E2 elimination of 3° alcohols can be accomplished using phosphorus oxychloride (POCl).3) in pyridine. This procedure also applies to 2nd hindered alcohols, but to free and 1st alcohols, pNO2 Chloride ion replacement and competition for elimination of the chlorophosphate intermediate. The following figure shows examples of this and related reactions. The first equation shows the dehydration of the 3º alcohol. It is hypothesized that the predominance of the non-Zaitsev (least substituted double bond) product is due to steric hindrance of the methylene hydrogen atom, which prevents base access at this site. The second example shows two elimination processes applied to the same second alcohol. The first uses a single stage POCl3Method that works well in this case because SNO2 Substitution is retarded by steric hindrance. The second approach is another example where the intermediate sulfonate ester imparts a halogen-like reactivity to the alcohol. In each case, the leaving group of the anion is the conjugate base of the strong acid.

    17.6 Alcoholic Reactions (25)

    alcohol to ester

    Acid chlorides react with alcohols to form esters.

    17.6 Alcoholic Reactions (26)

    17.6 Alcoholic Reactions (27)

    Example 17.6.3

    17.6 Alcoholic Reactions (28)


    Contributors and attribution


    What is the formula for the alcohol reaction? ›

    The reaction of alcohols with different elements, compounds, and molecule groups to give rise to a new compound is known as alcohol reaction. The general formula for alcohols is given as \( C_nH_{2n+1}OH \), C is the carbon atom, H represents the hydrogen atom and the OH group is the hydroxyl group.

    What is the reactivity of alcohol? ›

    The chemical reactivity of alcohols is related the presence of hydroxyl group. Three reactive sites for alcohol are carbon – hydroxyl group bond (C – OH bond), oxygen – hydrogen bond (O – H bond) and the hydrogen attached to α-carbon. These bonds are involved in chemical reactions of alcohols.

    What are the primary alcohol reactions? ›

    Nucleophilic Substitution, β-‐Elimination, and Oxidation reactions are the main type of reactions associated with alcohols.

    What is the dehydration of alcohol reaction? ›

    Alcohol upon reaction with protic acids tends to lose a molecule of water to form alkenes. These reactions are known as dehydrogenation or dehydration of alcohols. It is an example of an elimination reaction. Its rate varies for primary, secondary and tertiary alcohols.

    What is the order of reaction of alcohol? ›

    The order of reactivity of alcohols is 3° > 2° > 1° methyl. The order of reactivity of the hydrogen halides is HI > HBr > HCl (HF is generally unreactive).

    Is it possible to have an intolerance to alcohol? ›

    Alcohol intolerance can cause immediate, uncomfortable reactions after you drink alcohol. The most common signs and symptoms are stuffy nose and skin flushing. Alcohol intolerance is caused by a genetic condition in which the body can't break down alcohol efficiently.

    What type of alcohol is the most reactive? ›

    Ethanol because for the dissociation of O-H bond, 10 alcohols are the most reactive.

    Which alcoholic group is most reactive? ›

    The most reactive site in an alcohol molecule is the hydroxyl group, despite the fact that the O–H bond strength is significantly greater than that of the C–C, C–H and C–O bonds, demonstrating again the difference between thermodynamic and chemical stability.

    What are the different types of alcohol reactions? ›

    The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.

    What are 3 factors affecting individual reaction to alcohol? ›

    Mood: Emotions, such as stress, can change your stomach enzymes and affect how your body processes alcohol. Sex: Women tend to experience the effects of alcohol quicker and longer than men. Tolerance: The body's ability to adapt to the effects of alcohol.

    What is the tertiary alcohol reaction? ›

    The reaction of a tertiary alcohol with HBr or HCl to give a halide via a carbocation intermediate is a general reaction in which alcohols react with mineral acids (HCl, HBr, and HI) to give the corresponding alkylhalide.

    Which reaction produces 3 degree alcohol? ›

    Reacting a Grignard reagent with formaldehyde (H2C=O) produces 1o alcohols, aldehydes produce 2o alcohols, and ketones produce 3o alcohols.

    Which alcohol is most reactive for dehydration? ›

    Tertiary alcohols tend to be easier to dehydrate and primary alcohols to be the hardest.

    Why do alcoholics suffer from dehydration? ›

    Why does alcohol cause dehydration? Alcohol is a diuretic and therefore causes excessive urination. As a result, a person loses vital fluids and electrolytes.

    How do you get rid of alcohol dehydration? ›

    Here are five tips to help you:
    1. Eat plenty of food before drinking alcohol. Drinking on an empty stomach will speed up your blood alcohol levels so you get both drunk and dehydrated faster. ...
    2. Limit how much you drink. ...
    3. Stick to 'light' coloured drinks. ...
    4. Choose a lower alcohol content. ...
    5. Drink more water.
    Dec 17, 2021

    Which alcohol reacts faster? ›

    Tertiary alcohol reacts faster with hydrochloric acid with zinc chloride compared with secondary and primary alcohol. This reactivity is due to the carbocation stability. Secondary alcohol reacts faster with hydrochloric acid with zinc chloride compared with primary alcohol.

    Can primary alcohols be dehydrated? ›

    Primary alcohols dehydrate through the E2 mechanism. The hydroxyl oxygen donates two electrons to a proton from sulfuric acid (H2SO4), forming an alkyloxonium ion.

    Which alcohol react faster and what mechanism? ›

    Thus with Lucas reagent, tertiary alcohol reacts fastest and by SN1 mechanism.

    What are the first signs of liver damage from alcohol? ›

    Generally, symptoms of alcoholic liver disease include abdominal pain and tenderness, dry mouth and increased thirst, fatigue, jaundice (which is yellowing of the skin), loss of appetite, and nausea. Your skin may look abnormally dark or light. Your feet or hands may look red.

    How do you know if your sensitive to alcohol? ›

    But the hallmark symptom of alcohol intolerance is flushing of the skin of the chest, neck and face. Symptoms of an alcohol allergy include rashes, itchiness, swelling and severe stomach cramps. Allergy symptoms are often more painful and uncomfortable than alcohol intolerance symptoms.

    What disease causes sudden alcohol intolerance? ›

    Alcohol Intolerance as a Result of Disease

    Certain diseases can affect how well alcohol dehydrogenase functions. Hodgkin's lymphoma, ovarian cancer, breast cancer and other diseases can all cause a sudden onset of alcohol intolerance in those who never before experienced difficulty drinking.

    Which alcohol is most stable? ›

    The difference in the reactivity of the degrees of alcohol provides the differing ease of formation of the corresponding carbocations. The primary carbocation is least stable followed by secondary carbocation and the tertiary alcohols form the most stable tertiary carbocations.

    What is the order of reactivity of alcohol with reason? ›

    The order of reactivity of alcohols is 3° > 2° > 1° methyl. The order of reactivity of the hydrogen halides is HI > HBr > HCl (HF is generally unreactive).

    What is a monofunctional alcohol? ›

    For the monofunctional alcohols, this common system consists of naming the alkyl group followed by the word alcohol. Alcohols may also be classified as primary, 1º; secondary, 2º & tertiary, 3º, in the same manner as alkyl halides.

    Are primary alcohols more reactive? ›

    Thus, primary alcohols have maximum reactivity and tertiary alcohols have minimum reactivity.

    What are the two types of alcoholic? ›

    The two subtypes identified in this typology are called type I (milieu-limited) and type II (male-limited) alcoholism.

    What are the three types of alcohol tolerance? ›

    • National Institute on Alcohol Abuse and Alcoholism No. 28 PH 356 April 1995.
    • Alcohol and Tolerance.
    • Functional Tolerance.
    • Acute tolerance. ...
    • Environment-dependent tolerance. ...
    • Learned tolerance. ...
    • Metabolic Tolerance.
    • Tolerance and the Predisposition to Alcoholism.

    What are the three types of alcohol drinkers? ›

    There are three main categories that users of alcohol fall into; social drinker, alcohol abuser or alcoholic.

    Why do some people react to alcohol differently? ›

    Genetics. Alcohol is broken down through the work of three enzymes. Research shows that different people can have variations of the gene that produces these enzymes. The differences in these enzymes mean that some people metabolize alcohol differently from others.

    What are two common effects alcohol has on a person's Behaviour? ›

    Alcohol affects the part of your brain that controls inhibition, so you may feel relaxed, less anxious, and more confident after a drink. But these effects quickly wear off. The chemical changes in your brain can soon lead to more negative feelings, such as anger, depression or anxiety, regardless of your mood.

    What does it mean to blackout from alcohol? ›

    Alcohol-related blackouts are gaps in a person's memory for events that occurred while they were intoxicated. These gaps happen when a person drinks enough alcohol to temporarily block the transfer of memories from short-term to long-term storage—known as memory consolidation—in a brain area called the hippocampus.

    How do you test the stability of alcohol? ›

    Hint: The stability of alcohols depends on the strength of the C—O bond in the alcohols. Greater the strength of the C—O bond or stronger the C—O bond, greater is the stability of the alcohols.

    What is 2 degree alcohol? ›

    A secondary alcohol has the hydroxyl group on a secondary (2°) carbon atom, which is bonded to two other carbon atoms. Similarly, a tertiary alcohol has the hydroxyl group on a tertiary (3°) carbon atom, which is bonded to three other carbons.

    What is a positive result with tertiary alcohol? ›

    A positive test is indicated by a change from clear and colourless to turbid, signalling formation of a chloroalkane. Also, the best results for this test are observed in tertiary alcohols, as they form the respective alkyl halides fastest due to higher stability of the intermediate tertiary carbocation.

    How do you test for secondary alcohol? ›

    A secondary alcohol is identified by the color change with the acidified potassium dichromate(VI) solution and the absence of a color change with the Schiff's reagent might.

    Can a tertiary alcohol be reduced? ›

    Benzylic alcohols, secondary alcohols, and tertiary alcohols were effectively reduced to give the corresponding alkanes in high yields. A compound bearing both primary and secondary hydroxyl groups was reduced only at the secondary site to afford the primary alcohol after workup with Bu4NF.

    How will you distinguish between 1 degree 2 degree and 3 degree alcohol? ›

    Primary alcohol gives blood-red colour, secondary alcohol gives blue and tertiary alcohol remains colourless.

    What level of alcohol is hydrating? ›

    The study suggests that beverages with low alcohol concentrations have “a negligible diuretic effect” when consumed in a state of exercise-induced dehydration, meaning that hydrating with water or a low-alcohol beer (~2% ABV) is effectively the same.

    Does being dehydrated make alcohol stronger? ›

    Although heat and dehydration themselves will not make you drunk, they can intensify the effects of alcohol. You may be more likely to be arrested for driving under the influence (DUI), therefore, after drinking on a hot day.

    Does alcohol dehydrate you more than hydrate? ›

    One of the main causes of a hangover is dehydration, and drinking alcohol dehydrates you faster thanks to its diuretic effects. When your body senses that you're getting dehydrated in general, it produces a hormone called Vasopressin which reduces the need to urinate.

    What are the first signs of kidney damage from alcohol? ›

    What are the first signs of kidney damage from alcohol?
    • fatigue.
    • swelling of the legs, ankles, and feet due to fluid retention.
    • loss of appetite.
    • change in urine.
    • kidney pain.
    Apr 26, 2022

    Does drinking water help alcoholics? ›

    Even moderate levels of alcohol have a dehydrating effect, and drinking water can slow this effect down. When a person hydrates by drinking plenty of water, it can give their liver time to metabolize the alcohol in their body, as well as spacing out the alcoholic drinks they consume.

    Why do I feel weird 2 days after drinking? ›

    For example, the liver will be overworking to process alcohol, you'll be tired from little and/or poor quality sleep, you're likely to be urinating more as alcohol is a diuretic, leaving you dehydrated and headache-y – and any post-night out vomiting can irritate the stomach for several days. '

    How many glasses of water to rehydrate after alcohol? ›

    Have at least one 16-ounce glass of water with every 12-ounce beer or 4 to 6 ounces of liquor, for example. Water can replenish your fluids and help you stay hydrated. Stick with light-colored drinks.

    How long does it take to recover from alcohol dehydration? ›

    It depends on a variety of factors such as how dehydrated you are and how much water you drink at once. In general, however, it usually takes about two hours for your body to rehydrate fully after drinking a significant amount of water.

    Is dehydration of alcohol reversible? ›

    Dehydration is Reversible

    Dehydration is a reversible reaction- under the same conditions (water in the presence of acid), alkenes can be converted right back into alcohols (see Carey CH 6.10).

    What does reactivity of alcohol depend on? ›

    The order of reactivity depends on the acidic strength of the types of alcohol i.e. primary, secondary, and tertiary alcohols. Acids that have higher acidic strength react with sodium faster as compared to weaker acids.

    What is the reactivity of ethanol? ›

    ETHANOL reacts violently with acetyl chloride and acetyl bromide [Rose, (1961); Merck 11th ed., 1989]. Mixtures with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Mixtures with concentrated hydrogen peroxide form powerful explosives.

    What is the order of reactivity of alcohols with active metals? ›

    The reactivity of alcohols towards sodium follows the order primary>secondary>tertiary.

    Why is the reactivity of all the three classes of alcohols? ›

    The reactivity of all the three classes of alcohols with concentrated HCl and ZnCl2 (Lucas reagent) is different because of the steric hindrance of the alkyl groups and the stability of the carbocation. Primary alcohol does not show any reaction at room temperature because the 1° carbocation is least stable.

    What are 3 factors that affect the rate of alcohol absorption? ›

    Factors affecting alcohol absorption
    • Food. The amount and type of food present in the digestive tract has the most direct and measurable effect upon the rate of alcohol absorption. ...
    • Speed of ingestion of alcohol. ...
    • Cigarette smoking. ...
    • Type and strength of alcohol. ...
    • Gender. ...
    • Stomach diseases. ...
    • Physiological state. ...
    • Age.

    How does alcohol affect reaction rate? ›

    Studies have shown that increasing BAC is also associated with a decreased reaction time. One study pointed to an average decreased reaction time of 120 milliseconds — just over a tenth of a second — associated with a BAC level of 0.08, the legal limit in the United States.

    Why are alcohols more reactive? ›

    The functional group of the alcohols is the hydroxyl group, –OH. Unlike the alkyl halides, this group has two reactive covalent bonds, the C–O bond and the O–H bond. The electronegativity of oxygen is substantially greater than that of carbon and hydrogen.

    Which alcohol is more stable? ›

    The difference in the reactivity of the degrees of alcohol provides the differing ease of formation of the corresponding carbocations. The primary carbocation is least stable followed by secondary carbocation and the tertiary alcohols form the most stable tertiary carbocations.

    Why are some alcohols more reactive than others? ›

    Tertiary alcohols are more reactive because the increased number of alkyl groups increases +I effect. So, the charge density on carbon atom increases and hence around oxygen atom.

    What metals react with alcohol? ›

    We know that alcohols react with active metals e.g. Na, K, etc. to give corresponding alkoxides. Alcohols contain hydrogen attached to oxygen. Compounds containing hydrogen attached more electronegative elements such as oxygen are acidic.

    Which of the following alcohol can be most easily dehydrated? ›

    Tertiary alcohols undergo dehydration very fast.

    Which is more reactive alcohol or water? ›

    This reaction shows that water is a better proton donor (i.e., stronger acid) than alcohol. Also, in the above reaction, we note that an alkoxide ion is a better proton acceptor than hydroxide ion, which suggests that alkoxides are stronger bases (sodium ethoxide is a stronger base than sodium hydroxide).

    Which alcohol is more reactive primary or tertiary? ›

    Tertiary alcohols are more reactive than primary alcohols due to the higher amount of alkyl groups in the compound, which amplifies the +I effect. As a result, the charge density on the carbon atom increases, and the charge density around the oxygen atom increases as well. ANS.


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    Address: Suite 461 73643 Sherril Loaf, Dickinsonland, AZ 47941-2379

    Phone: +2678139151039

    Job: International Administration Supervisor

    Hobby: Dowsing, Snowboarding, Rowing, Beekeeping, Calligraphy, Shooting, Air sports

    Introduction: My name is Catherine Tremblay, I am a precious, perfect, tasty, enthusiastic, inexpensive, vast, kind person who loves writing and wants to share my knowledge and understanding with you.