(a)
Interpretation:
The molecule that has higher boiling point among the given molecules has to be identified.
Concept Introduction:
Carbonyl groups are the one which contain a double bond between carbon and oxygen atom.
Aldehydes contain a carbonyl group that contains a hydrogen atom and a carbon atom bonded to it. Aldehyde that has one and two carbon atoms are gas at room temperature. The physical state of aldehyde that contains three carbon atoms to eleven carbon atoms that are not branched is liquid at room temperature. Aldehydes that contain more than eleven carbon atoms are solid at room temperature.
Ketones contain a carbonyl group that contains two carbon atoms bonded to it. For a compound to be ketone, a minimum of three carbon atom is required. Ketones that contain three carbon atoms to eight carbon atoms which have the carbonyl group at the second carbon atom are liquid at room temperature.
Boiling point is the temperature at which the liquid state gets converted into gaseous state. Aldehydes and ketones have their boiling points intermediate between the boiling points of alcohols and
(b)
Interpretation:
The molecule that has higher boiling point among the given molecules has to be identified.
Concept Introduction:
Carbonyl groups are the one which contain a double bond between carbon and oxygen atom. Aldehydes and ketones possess this carbonyl functional group in it. The structural representation of a carbonyl group can be given as shown below,
Aldehydes contain a carbonyl group that contains a hydrogen atom and a carbon atom bonded to it. Aldehyde that has one and two carbon atoms are gas at room temperature. The physical state of aldehyde that contains three carbon atoms to eleven carbon atoms that are not branched is liquid at room temperature. Aldehydes that contain more than eleven carbon atoms are solid at room temperature.
Ketones contain a carbonyl group that contains two carbon atoms bonded to it. For a compound to be ketone, a minimum of three carbon atom is required. Ketones that contain three carbon atoms to eight carbon atoms which have the carbonyl group at the second carbon atom are liquid at room temperature.
Boiling point is the temperature at which the liquid state gets converted into gaseous state. Aldehydes and ketones have their boiling points intermediate between the boiling points of alcohols and alkanes with similar molecular mass. Due to the dipole‑dipole interaction, aldehydes and ketones have higher boiling point than alkanes. Due to the absence of hydrogen bonding in aldehyde and ketones, they have lower boiling points than alcohols of similar molecular mass.
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Chapter 4 Solutions
EBK ORGANIC AND BIOLOGICAL CHEMISTRY
- Synthesis of ZybanⓇ: 1. Write a mechanism for the bromination of m-chloropropiophenone. Br₂ CH2Cl2 Cl Br 2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks). 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAcid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Assign this H NMRarrow_forwardPlease complete these blanks need that asaparrow_forwardNitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Sodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 1: 1. What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to 1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the following rearranged product is not formed. محرم محمد 3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
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