Based on shape, what is the predicted relative solubility of 1-butanol, isobutanol, and tert-butanol? Based on size, what is the predicted relative solubility of 1-butanol and 1-pentanol?

There is nothing like 1- butanone , it's a wrong name ,right name of compound is 2- butanone or butanone ,both are same. So we now have three compounds butane , butanone and butanol.

In order to know which compound is more acidic we must check there corresponding conjugate base , more stable the conjugate base , stronger will be the acid because it is less likely to accept proton and form acid again. Less stable the conjugate base ,weaker will be the acid .

Conjugate base of given compounds are -

CH2CH2CH2CH2–

CH3 CH2 CO CH2–

CH3CH2CH2CH2O-

We can tell stability of any conjugate base on the basis of five factors.

1. Charge
2. Atom
3. Resonance
4. Induction

5) orbital

Two of the three compounds have charge on carbon atom and third have charge on oxygen atom, there is no much size difference between the two but being a stronger electronegative atom oxygen can hold that negative charge more effectively than carbon atom hence butanol will be most acidic.

Now out of butane and butanone , butanone will be more acidic because it's conjugate base will be more stabilize by resonance .

Hence order of acidic strength-

Butanol> butanone>butane

Because butan-1-ol has a CH_2OH group while butan-2-ol has a CHOH group.

Alcohols oxidize by sacrificing the hydrogen on the OH group and one extra hydrogen from the carbon atom the OH group is on to form a carboxyl group.

Primary alcohols, like butan-1-ol, have two hydrogen on the carbon atom.

$RCH_2OH + [O] > RCHO$

Secondary alcohols, like butam-2-ol, have only one hydrogen to remove

$RCHOHR + [O] > RCOR$

Chances of a hydrogen atom falling off is greater when there are two. Thus primary alcohols oxidize more readily than secondary alcohols.

—Gt. Yuhan Zhang (Proud A-level Chemistry student)

The bases which are soluble in water is called alkali. As for example, NaOH ia an alkali because it is soluble in water.

The solubility increases with increase in the number of branches because increase in branching increases the surface area of non polar hydrocarbon.

Order of solubility is

Tert- botanol > iso butanol > 1- butanol.

As the hydrogen cabon chain length increases, covalent nature increases ans solubility decreases . So 1- butanol is more soluble than that of 1-pentanol.

It has to do with the concept of chemical polarity. The chemical polarity refers to the separation of electrical charge with respect to the actual molecule itself. It is solely dependent on the atom species constituting the molecule and there electronegativity. The electronegativity describes the tendency of an atom to attract electrons towards itself. As a consequence, we speak about non-polar and polar molecules. The polar molecules have intra molecular charge separation whereas the non-polar has not. The concept of electronegativity was first introduced by the Swedish chemist Jöns Jacob Berzelius in 1811.

The two major solvents in organic chemistry are commonly referred to as water solution and organic solution. The prior (water) is very polar, due to the oxygen atom with high electronegativity, and the other (organic phase) is normally very non-polar due to the structure and symmetry of organic molecules that normally has long hydrocarbon chains with low intra molecular charge separation.

Coming back to your question. Methanol is a very small molecule consisting of only one carbon atom, a few hydrogen atoms and one hydroxyl group (-OH). The buthanol molecule comprises of a longer hydrocarbon chain (four carbons) and one -OH. Due to the longer hydrocarbon chain of buthanol, it is less polar and consequently less soluble in water compared to methanol.

Well From Ethanol to Butanol , lets give this a try !

• Reaction of Ethanol with HCl to give ChloroEthane ( CH3- CH2 -Cl ) [ another alternative is reaction with NaCl in presence of H2SO4 to give out the same product )
• Reaction of 2 moles ChloroEthane in presence of dry ether and Na (Wurtz Reaction) and alternative is Frankland Reaction ( Usage of Zn replacing Na ) to give Butane !
• Reaction of Butane in presence of sunlight with Cl2 to give ChloroButane ( CH3-CH2-CH2-CH2-Cl)
• Reaction with KOH (aq) to give Butanol

:)

As we move from 1- butanol to tert-butanol, the solubility decreases because of the increase in the steric hindrance due to which tendency to form hydrogen bonds with water decreases.

1-pentanol is less soluble in water compared to 1- butanol, due larger hydrophobic part in 1-pentanol.

Butanol

1-Butanol and isobutyl alcohol have limited solubility (less than 10g/100ml), t-butyl alcohol, with a more compact hydrophobic region, is miscible with water.

With the use of a catalyst such as dry ZnCl2, you can get 1-chlorobutane and water. This reaction can probably be carried out without a catalyst if the reagents are subject to reflux for extended periods of time, but I would expect it to be rather slow under such conditions.

Butanol.
It's an alcohol i.e. it has an O-H group which is polar. Now because of this, it can form H Bond with water, which is also polar H-O-H.
Butane on the other hand, is a non polar molecule and thus isn't likely to dissolve in a polar solvent.