Why do double bonds cause kinks in fatty acid chains?
Clash Royale CLAN TAG#URR8PPP
$begingroup$
Fatty acids can either be saturated or unsaturated. If they are saturated, they stack easily and form solids at room temperature. If they are unsaturated, however, double bonds are introduced, and these double bonds introduce kinks into the structure of the fatty acid molecule. In a different question on this site, it was suggested that the reason why double bonds cause kinks to form is that they interrupt the zig zag shape of the molecule.
However, what was left unexplained is how double bonds interrupt the zig zag shape. If we were dealing with a cis fatty acid, and both hydrogens were located on top, why would this lead to a kink?
organic-chemistry
asked Feb 3 at 20:36
KorvexiusKorvexius
154
$endgroup$
add a comment |
$begingroup$
Fatty acids can either be saturated or unsaturated. If they are saturated, they stack easily and form solids at room temperature. If they are unsaturated, however, double bonds are introduced, and these double bonds introduce kinks into the structure of the fatty acid molecule. In a different question on this site, it was suggested that the reason why double bonds cause kinks to form is that they interrupt the zig zag shape of the molecule.
However, what was left unexplained is how double bonds interrupt the zig zag shape. If we were dealing with a cis fatty acid, and both hydrogens were located on top, why would this lead to a kink?
organic-chemistry
asked Feb 3 at 20:36
KorvexiusKorvexius
154
$endgroup$
add a comment |
$begingroup$
Fatty acids can either be saturated or unsaturated. If they are saturated, they stack easily and form solids at room temperature. If they are unsaturated, however, double bonds are introduced, and these double bonds introduce kinks into the structure of the fatty acid molecule. In a different question on this site, it was suggested that the reason why double bonds cause kinks to form is that they interrupt the zig zag shape of the molecule.
However, what was left unexplained is how double bonds interrupt the zig zag shape. If we were dealing with a cis fatty acid, and both hydrogens were located on top, why would this lead to a kink?
organic-chemistry
asked Feb 3 at 20:36
KorvexiusKorvexius
154
$endgroup$
Fatty acids can either be saturated or unsaturated. If they are saturated, they stack easily and form solids at room temperature. If they are unsaturated, however, double bonds are introduced, and these double bonds introduce kinks into the structure of the fatty acid molecule. In a different question on this site, it was suggested that the reason why double bonds cause kinks to form is that they interrupt the zig zag shape of the molecule.
However, what was left unexplained is how double bonds interrupt the zig zag shape. If we were dealing with a cis fatty acid, and both hydrogens were located on top, why would this lead to a kink?
organic-chemistry
organic-chemistry
asked Feb 3 at 20:36
KorvexiusKorvexius
154
asked Feb 3 at 20:36
KorvexiusKorvexius
154
asked Feb 3 at 20:36
KorvexiusKorvexius
154
asked Feb 3 at 20:36
KorvexiusKorvexius
154
asked Feb 3 at 20:36
KorvexiusKorvexius
154
154
add a comment |
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
Instead of zig-zag, zig-zag, zig-zag etc. it now goes zig-zag, zig, zig-zag, zig- etc (the bold zig is due to the cis double bond). So the direction of the alkyl chain on one side of the cis double bond is different from that of the alkyl chain on the other. You could partially correct for that "wrong turn" by rotating a single bond by $180^circ$, but that changes a staggered conformation into an eclipsed one.
Here is a link to a 3D model: http://www.biotopics.co.uk/jsmol/fattyacids.html and a snapshot in case the link goes away:
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
$endgroup$
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
add a comment |
Your Answer
StackExchange.ifUsing("editor", function ()
return StackExchange.using("mathjaxEditing", function ()
StackExchange.MarkdownEditor.creationCallbacks.add(function (editor, postfix)
StackExchange.mathjaxEditing.prepareWmdForMathJax(editor, postfix, [["$", "$"], ["\\(","\\)"]]);
);
);
, "mathjax-editing");
StackExchange.ready(function()
var channelOptions =
tags: "".split(" "),
id: "431"
;
initTagRenderer("".split(" "), "".split(" "), channelOptions);
StackExchange.using("externalEditor", function()
// Have to fire editor after snippets, if snippets enabled
if (StackExchange.settings.snippets.snippetsEnabled)
StackExchange.using("snippets", function()
createEditor();
);
else
createEditor();
);
function createEditor()
StackExchange.prepareEditor(
heartbeatType: 'answer',
autoActivateHeartbeat: false,
convertImagesToLinks: false,
noModals: true,
showLowRepImageUploadWarning: true,
reputationToPostImages: null,
bindNavPrevention: true,
postfix: "",
imageUploader:
brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/3.0/"u003ecc by-sa 3.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
allowUrls: true
,
onDemand: true,
discardSelector: ".discard-answer"
,immediatelyShowMarkdownHelp:true
);
);
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function ()
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f108976%2fwhy-do-double-bonds-cause-kinks-in-fatty-acid-chains%23new-answer', 'question_page');
);
Post as a guest
Required, but never shown
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
Instead of zig-zag, zig-zag, zig-zag etc. it now goes zig-zag, zig, zig-zag, zig- etc (the bold zig is due to the cis double bond). So the direction of the alkyl chain on one side of the cis double bond is different from that of the alkyl chain on the other. You could partially correct for that "wrong turn" by rotating a single bond by $180^circ$, but that changes a staggered conformation into an eclipsed one.
Here is a link to a 3D model: http://www.biotopics.co.uk/jsmol/fattyacids.html and a snapshot in case the link goes away:
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
$endgroup$
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
add a comment |
$begingroup$
Instead of zig-zag, zig-zag, zig-zag etc. it now goes zig-zag, zig, zig-zag, zig- etc (the bold zig is due to the cis double bond). So the direction of the alkyl chain on one side of the cis double bond is different from that of the alkyl chain on the other. You could partially correct for that "wrong turn" by rotating a single bond by $180^circ$, but that changes a staggered conformation into an eclipsed one.
Here is a link to a 3D model: http://www.biotopics.co.uk/jsmol/fattyacids.html and a snapshot in case the link goes away:
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
$endgroup$
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
add a comment |
$begingroup$
Instead of zig-zag, zig-zag, zig-zag etc. it now goes zig-zag, zig, zig-zag, zig- etc (the bold zig is due to the cis double bond). So the direction of the alkyl chain on one side of the cis double bond is different from that of the alkyl chain on the other. You could partially correct for that "wrong turn" by rotating a single bond by $180^circ$, but that changes a staggered conformation into an eclipsed one.
Here is a link to a 3D model: http://www.biotopics.co.uk/jsmol/fattyacids.html and a snapshot in case the link goes away:
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
$endgroup$
Instead of zig-zag, zig-zag, zig-zag etc. it now goes zig-zag, zig, zig-zag, zig- etc (the bold zig is due to the cis double bond). So the direction of the alkyl chain on one side of the cis double bond is different from that of the alkyl chain on the other. You could partially correct for that "wrong turn" by rotating a single bond by $180^circ$, but that changes a staggered conformation into an eclipsed one.
Here is a link to a 3D model: http://www.biotopics.co.uk/jsmol/fattyacids.html and a snapshot in case the link goes away:
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
edited Feb 3 at 21:10
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
answered Feb 3 at 21:03
Karsten TheisKarsten Theis
2,003324
2,003324
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
add a comment |
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
Is there an extra zig because of the hydrogen on the next carbon occupying the region where the next carbon would have needed to go to form the next zag? (and if so, can you add it to your answer?)
$endgroup$
– Korvexius
Feb 3 at 21:13
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
$begingroup$
A cis-bond itself is a zig-zig (or U-shaped) while a trans-bond is zig-zag (just like a single bond in staggered antiperiplanar conformation). So yes, compared to the trans-bond you are swapping the single bonds to hydrogen and to the carbon on one side of the double bond.
$endgroup$
– Karsten Theis
Feb 3 at 21:23
add a comment |
Thanks for contributing an answer to Chemistry Stack Exchange!
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
Use MathJax to format equations. MathJax reference.
To learn more, see our tips on writing great answers.
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function ()
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f108976%2fwhy-do-double-bonds-cause-kinks-in-fatty-acid-chains%23new-answer', 'question_page');
);
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
