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Polar and Non-Polar molecules/ Hydrogen Bonding?

Hi. Which of the following molecules cannot form hydrogen bonding with water molecules?

  • a) CH3CH2OCH2CH3 b) CH3CH2CH2CHO c) CH3CH2CH2Cl d) CH3CH2CH2COOH I know that hydrogen bonding only occurs where the electronegativity difference is high - bonding between hydrogen and chlorine, hydrogen and fluorine, hydrogen and oxygen... But can someone explain the answer to this question for me? Thank you very much

  • Answer:

    Easy peasy - when you know how! Well Hydrogen is pretty short of electrons when bonded it is sharing the only one it has! Therefore its best friends are those with lots or the electronegative elements that have lots of free electrons! Most notably these are Oxygen and Nitrogen. You see atoms with like these are called electronegative - they like to pull electron density (bunches of electrons) towards them and form a slight negative charge, so when Hydrogen has its one electron pulled away it forms a slight positive charge. These slight charges are called induced dipoles (dipoles really). So say your a hydrogen over here: -------------H and you have had your electron taken away from you and have a slight positive charge! you like to bond to: ----------H O------------ or ---------H N------------- and that is hydrogen bonding. Chlorine can bond in this way but it is a large atom and is not very electronegative where as Oxygen and Nitrogen loves this little guy! I know this has been long winded and Im sorry! But you wont get confused again!

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c... The others are alcohols and will combine.

Norrie

correct choice is C.chlorine never makes hydrogen bond . only nitrogen,oxygen and fluorine do.

i am the guy!!

None of them can form without the presence of carbon. Please restate the problem more clearly.

ksoileau

A, B, and D will all H bond with H2O due to the lone pairs of electrons on the oxygens. C will not H bond

drochem

Im pretty sure it is C.

Magic D

Drawing these out shows: A) This is a keytone, I.e. a C-C(O)-C bond, where the C(O) is a C=O (double bond). Therefore, the O has 2 lone pair of electrons and can participate in hydrogen bonding with water. B) This is an aldehyde. This has a C=O bond also at the end of the chain, and will therefore have 2 lone pairs of electrons with which to participate in hydrogen bonding. C) This is a halogenoalkane. Although C-Cl is a polar bond, it is not polar enough to participate in hydrogen bonding. It should therefore be at least partially miscible with water, but it should not participate in hydrogen bonding with water. D) This is a carboxylic acid group. There is a C=O bond in this also, which means that this alkane will participate in hydrogen bonding in water. Potentially, the C-O-H could participate in hydrogen bonding, however, in a carboxylic acid the H becomes dissociated in the water as H+ ions (it's what makes this a carboxylic _acid_ group). The O-H bond does participate in hydrogen bonding in alchols.

tinned_tuna

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