{"id":8174,"date":"2014-05-14T11:55:29","date_gmt":"2014-05-14T15:55:29","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8174"},"modified":"2025-09-26T10:31:33","modified_gmt":"2025-09-26T15:31:33","slug":"an-aerial-tour-of-the-cyclohexane-chair","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/05\/14\/an-aerial-tour-of-the-cyclohexane-chair\/","title":{"rendered":"Cyclohexane Chair Conformation: An Aerial Tour"},"content":{"rendered":"<p><strong>A Fly-by Of The Cyclohexane Chair Conformation<\/strong><\/p>\n<p>Sometimes words just don&#8217;t do the job, so I built a model of the cyclohexane chair and took a whole bunch of videos and pictures of it to help you get the picture.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-42119\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/0-summary-aerial-view-of-the-cyclohexane-chair-only-a-hexagon-from-the-top-newman-projection-of-the-chair-cyclohexane-resembles-deck-chair.gif\" alt=\"summary-aerial view of the cyclohexane chair only a hexagon from the top newman projection of the chair cyclohexane resembles deck chair\" width=\"640\" height=\"582\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">A Seven-Second Video Tour Of The Cyclohexane Chair<\/a><\/li>\n<li><a href=\"#two\">It&#8217;s Only A Hexagon If You Look At It From The Top<\/a><\/li>\n<li><a href=\"#three\">A Side View Of The Cyclohexane Chair Reveals That All C\u2013C Bonds Are Perfectly Staggered<\/a><\/li>\n<li><a href=\"#four\">A Newman Projection Of The Cyclohexane Chair<\/a><\/li>\n<li><a href=\"#five\">The &#8220;Classic View&#8221; of The Cyclohexane Chair<\/a><\/li>\n<li><a href=\"#six\">Groups Pointing Straight Up And Straight Down Are In The &#8220;Axial&#8221; Position<\/a><\/li>\n<li><a href=\"#seven\">Groups Pointing Off To The Side Are In The &#8220;Equatorial&#8221; Position<\/a><\/li>\n<li><a href=\"#eight\">Important Point: Equatorial Groups Can Be Either &#8220;Up&#8221; Or &#8220;Down&#8221;<\/a><\/li>\n<li><a href=\"#nine\">Mapping out &#8220;Axial Up&#8221;, &#8220;Axial Down&#8221;, &#8220;Equatorial Up&#8221; and &#8220;Equatorial Down&#8221; On A Cyclohexane Chair<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. A Seven-Second Video Tour Of The Cyclohexane Chair<\/h2>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/l0ExrnIkPIcK3s89y\" width=\"480\" height=\"480\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/l0ExrnIkPIcK3s89y\">via GIPHY<\/a><\/p>\n<h2><a id=\"two\"><\/a>2. It&#8217;s Only A Hexagon If You Look At It From the Top<\/h2>\n<p><span style=\"line-height: 1.5em;\">When I first learned about the cyclohexane chair (as we did in the last post) I was in denial about its importance in organic chemistry. From an aesthetic standpoint, it bothered me that cyclohexane wasn&#8217;t a beautifully flat hexagon. The cyclohexane chair was so UGLY to me, and I felt disappointment that I actually had to learn about this hideous thing.\u00a0<\/span><\/p>\n<p><span style=\"line-height: 1.5em;\">If you&#8217;re a weirdo like me, then you might be having these feelings too, but you&#8217;re probably not. In any case in this post I want us to get as familiar with the chair as possible, and even learn to appreciate it &#8211; even if it might seem like an acquired taste.\u00a0<\/span><\/p>\n<p><span style=\"line-height: 1.5em;\">First of all, I&#8217;ve built a model of cyclohexane in\u00a0<\/span>its most stable conformation<span style=\"line-height: 1.5em;\">. Imagine you are in a tiny helicopter that is surveying the view of this model from a variety of angles. \u00a0As we swoop from the top to the side to more of an &#8220;oblique&#8221; view of this model, to get an idea where everything stands in space (see the video above).\u00a0<\/span><\/p>\n<p><span style=\"line-height: 1.5em;\">From above, cyclohexane is indeed appears to be a beautiful hexagon:<\/span><\/p>\n<p style=\"text-align: center;\"><span style=\"line-height: 1.5em;\"><img decoding=\"async\" class=\"aligncenter wp-image-14293\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-overview-of-cyclohexane-chair-from-top-with-model.png\" alt=\"overview-of-cyclohexane-chair-from-top-with-model\" width=\"355\" height=\"361\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-overview-of-cyclohexane-chair-from-top-with-model.png 442w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-overview-of-cyclohexane-chair-from-top-with-model-295x300.png 295w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-overview-of-cyclohexane-chair-from-top-with-model-320x326.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-overview-of-cyclohexane-chair-from-top-with-model-360x367.png 360w\" sizes=\"(max-width: 355px) 100vw, 355px\" \/><\/span><\/p>\n<h2 style=\"text-align: left;\"><span style=\"line-height: 1.5em;\"><a id=\"three\"><\/a>3. A Side View Newman Projection Of The Cyclohexane Chair Reveals That All C\u2013C Bonds Are Perfectly Staggered\u00a0<\/span><\/h2>\n<p style=\"text-align: left;\"><span style=\"line-height: 1.5em;\">However, as we<a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/04\/18\/ring-strain-in-cyclopentane-and-cyclohexane\/\"> learned in the last post<\/a>, if the cyclohexane were actually flat, then we\u2019d have considerable angle strain and torsional strain. And as \u00a0we &#8220;fly&#8221; from the top to the side, \u00a0we make two important observations: 1) the cyclohexane is not flat, and 2) in our &#8220;side&#8221; view, note how the view along each C-C bond reveals that there is a &#8220;staggered&#8221; conformation.\u00a0<\/span><\/p>\n<p style=\"text-align: left;\"><img decoding=\"async\" class=\"aligncenter wp-image-14294\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-side-view-of-cyclohexane-chair-model-showing-all-staggered.png\" alt=\"side-view-of-cyclohexane-chair-model-showing-all-staggered\" width=\"355\" height=\"289\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-side-view-of-cyclohexane-chair-model-showing-all-staggered.png 373w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-side-view-of-cyclohexane-chair-model-showing-all-staggered-300x245.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-side-view-of-cyclohexane-chair-model-showing-all-staggered-320x261.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-side-view-of-cyclohexane-chair-model-showing-all-staggered-360x293.png 360w\" sizes=\"(max-width: 355px) 100vw, 355px\" \/><\/p>\n<h2><a id=\"four\"><\/a>4. A Newman Projection Of The Cyclohexane Chair<\/h2>\n<p>To make this more obvious, we can also depict this as a Newman projection, which would look like this:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-42120 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/4-newman-projection-of-cyclohexane-chair-conformation-showing-all-c-c-bonds-staggered.gif\" alt=\"newman projection of cyclohexane chair conformation showing all c c bonds staggered\" width=\"640\" height=\"201\" \/><\/a><\/p>\n<p><span style=\"color: #993366;\"><em>Newman projection of the cyclohexane chair conformation. Notice how the orientation about each C-C bond is staggered<\/em><\/span><\/p>\n<p style=\"text-align: left;\">This is an important clue as to the stability of this conformation: <b>unlike other conformations of cyclohexane<\/b>, the orientation about each C\u2013C bond is staggered, which means that torsional strain is minimized.<\/p>\n<h2><a id=\"five\"><\/a>5. The Classic View Of The Cyclohexane Chair<\/h2>\n<p style=\"text-align: left;\">Now let&#8217;s &#8220;swoop&#8221; a little off to one side, so that we&#8217;re looking at our model from a slightly oblique angle. See how the model slightly (kinda-sorta) \u00a0resembles a deck chair?<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14296\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair.png\" alt=\"image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair\" width=\"555\" height=\"231\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair.png 600w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair-300x125.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair-320x133.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-image-of-cyclohexane-chair-with-head-rest-and-foot-rest-side-by-side-with-deck-chair-360x150.png 360w\" sizes=\"(max-width: 555px) 100vw, 555px\" \/><\/p>\n<p style=\"text-align: left;\"><span style=\"line-height: 1.5em;\">It might take some imagination to see this &#8211; here&#8217;s an image from a textbook that might make it more clear: Chair Girl (and Boat Dude)<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14297\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-image-from-textbook-of-cyclohexane-chair-and-cyclohexane-boat-chair-girl-and-boat-dude.jpg\" alt=\"image-from-textbook-of-cyclohexane-chair-and-cyclohexane-boat-chair-girl-and-boat-dude\" width=\"285\" height=\"214\" \/><\/span><\/p>\n<p style=\"text-align: left;\">Now let\u2019s look at the chair a little more closely.<\/p>\n<h2><a id=\"six\"><\/a>6. Groups Pointing Straight Up And Straight Down Are In The &#8220;Axial&#8221; Position<\/h2>\n<p style=\"text-align: left;\">First, do you see how some groups point straight up and straight down?\u00a0<strong>Those are called the \u201caxial\u201d groups<\/strong>. See how axial alternates, up-down-up-down-up-down (12 o&#8217;clock to 6 o&#8217;clock and back again).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42127\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2014\/05\/7-model-of-cyclohexane-chair-with-axial-groups-labelled-in-pink-cyclohexane-chair-drawing-update.gif\" alt=\"model of cyclohexane chair with axial groups labelled in pink cyclohexane chair drawing-update\" width=\"640\" height=\"293\" \/><\/a><\/p>\n<h2><a id=\"seven\"><\/a>7. Groups Pointing Off To The Side Are In The &#8220;Equatorial&#8221; Position<\/h2>\n<p style=\"text-align: left;\">Then, there are groups which point off to the side. We call these the \u201cequatorial\u201d groups, as they are in line with certain of the bonds of the ring. \u00a0 They alternate from \u201csomewhat up\u201d (10 o&#8217;clock and 2 o&#8217;clock, if you use a clock face analogy) to \u201csomewhat down\u201d (8 o&#8217;clock and 4 o&#8217;clock).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42122\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/8-model-of-cyclohexane-chair-with-equatorial-groups-labelled-in-green.gif\" alt=\"model of cyclohexane chair with equatorial groups labelled in green\" width=\"640\" height=\"279\" \/><\/a><\/p>\n<p style=\"text-align: left;\"><span style=\"line-height: 1.5em;\">Now comes an important point &#8211;<\/span><strong style=\"line-height: 1.5em;\"> one which I had a hard time appreciating the first time I learned about chairs.\u00a0<\/strong><\/p>\n<p>\u00a0It\u2019s easy to see that the axial groups which point to 12 o\u2019clock are \u201cup\u201d and and groups which point to 6 o\u2019clock are considered \u201cdown\u201d.<\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Important Point: Equatorial Groups Can Be &#8220;Up&#8221; And &#8220;Down&#8221; Too<\/strong><\/h2>\n<p>Here&#8217;s the thing. Each carbon has one &#8220;up&#8221; group and one &#8220;down&#8221; group, and also one &#8220;axial&#8221; group and one &#8220;equatorial&#8221; group. So if a carbon is attached to a group that is &#8220;axial up&#8221;,\u00a0<strong>the down group must be equatorial.<\/strong> Likewise a carbon attached to an &#8220;axial down&#8221; group\u00a0<strong>must have an &#8220;up&#8221; group that is equatorial<\/strong>.\u00a0<strong><br \/>\n<\/strong><\/p>\n<p>It took awhile for me to appreciate that\u00a0<strong>equatorial groups can be &#8220;up&#8221; and &#8220;down&#8221; too<\/strong> &#8211; even though they don&#8217;t point &#8220;straight&#8221; up and down.<\/p>\n<p>Let\u2019s go back to the \u201ctop\u201d view of the cyclohexane. The groups which are \u201cup\u201d will be coming \u201ctowards\u201d us in the page &#8211; wedges , in other words, since we&#8217;re looking from the top down. \u00a0The groups which are &#8220;down&#8221; will be pointing away from us (dashes). First, let&#8217;s take that top view of cyclohexane and put dots where the axial groups are (they&#8217;re either pointing towards us [pink] or away from us [yellow]). And let&#8217;s colour the bonds to the equatorial group whether they point towards us (green) or away from us (blue).<br \/>\n<strong><br \/>\n<\/strong>Here&#8217;s the &#8220;top down&#8221; picture, colour coded for attempted clarity, and arbitrarily calling the carbon at the top &#8220;Carbon #1&#8221; and numbering clockwise.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42124\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/9-top-down-view-of-cyclohexane-with-all-axial-and-equatorial-groups-labelled-different-colors-color-coded.gif\" alt=\"top down view of cyclohexane with all axial and equatorial groups labelled different colors color coded\" width=\"640\" height=\"403\" \/><\/a><\/p>\n<p>It&#8217;s hard to see &#8220;up&#8221; and &#8220;down&#8221; on the model when we&#8217;re looking at it from this angle because one group on each carbon will be occluded.\u00a0Note that in the &#8220;Chemdraw version&#8221; we want to show that the groups are there (not hidden behind the carbons) so we cheat them out to the side a bit.<\/p>\n<h2><a id=\"nine\"><\/a>9. Mapping Out &#8220;Axial Up&#8221;, &#8220;Axial Down&#8221;, &#8220;Equatorial Up&#8221;, &#8220;Equatorial Down&#8221; On A Cyclohexane Chair<\/h2>\n<p><span style=\"line-height: 1.5em;\">Now let&#8217;s take this same\u00a0<\/span>colour<span style=\"line-height: 1.5em;\">\u00a0<\/span>scheme and map it on to the other views of the cyclohexane we&#8217;ve seen.\u00a0<span style=\"line-height: 1.5em;\">\u00a0<\/span><\/p>\n<p>Here&#8217;s the side-on (Newman) view, using the same numbering (although must numbers are omitted for clarity).<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42125\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/10-side-view-of-cyclohexane-chair-conformation-staggered-dowing-groups-axial-up-equatorial-up.gif\" alt=\"side view of cyclohexane chair conformation staggered dowing groups axial up equatorial up\" width=\"640\" height=\"284\" \/><\/a><\/p>\n<p>And here&#8217;s the &#8220;oblique&#8221; view (the &#8220;normal&#8221; chair view , in other words) using the same colour scheme.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42126\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/11-cyclohexane-chair-perspective-view-using-color-coding-showing-axial-up-equatorial.gif\" alt=\"-cyclohexane chair perspective view using color coding showing axial up equatorial\" width=\"640\" height=\"296\" \/><\/a><\/p>\n<p>I hope this post has been helpful in helping to identify &#8220;axial&#8221;, &#8220;equatorial&#8221;, &#8220;up&#8221; and &#8220;down&#8221; groups in the cyclohexane chair conformation. In the next post we&#8217;ll talk about\u00a0<strong>how to draw a cyclohexane chair.\u00a0<\/strong><\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/05\/20\/how-to-draw-a-cyclohexane-chair\/\">How To Draw A Cyclohexane Chair<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/04\/18\/ring-strain-in-cyclopentane-and-cyclohexane\/\" class=\"\"><span>Cyclohexane Conformations<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/05\/20\/how-to-draw-a-cyclohexane-chair\/\" class=\"\"><span>How To Draw The Cyclohexane Chair Conformation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/06\/06\/the-cyclohexane-chair-flip-energy-diagram\/\" class=\"\"><span>The Cyclohexane Chair Flip \u2013 Energy Diagram<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/07\/23\/which-cyclohexane-chair-is-of-lower-energy\/\" class=\"\"><span>Cyclohexane Chair Conformation Stability: Which One Is Lower Energy?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/08\/05\/fused-rings\/\" class=\"\"><span>Fused Rings \u2013 Cis-Decalin and Trans-Decalin<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/09\/02\/bredts-rule-and-summary-of-cycloalkanes\/\" class=\"\"><span>Bredt\u2019s Rule (And Summary of Cycloalkanes)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/08\/14\/bridged-bicyclic-compounds-and-how-to-name-them\/\" class=\"\"><span>Naming Bicyclic Compounds \u2013 Fused, Bridged, and Spiro<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/03\/24\/cycloalkanes-how-to-calculate-ring-strain\/\" class=\"\"><span>Calculation of Ring Strain In Cycloalkanes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/cycloalkanes-practice-problems\/\" class=\"\"><span>Cycloalkanes Practice Problems (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><span style=\"line-height: 1.5em;\"><strong><a id=\"noteone\"><\/a>Note 1.<\/strong>\u00a0 Sorry to disappoint, but I regret to inform you that the &#8220;<a href=\"http:\/\/eusoniptera.blogspot.co.il\/2011\/11\/shared-by-my-chem-prof.html\">Budweiser projection<\/a>&#8221; of a chair is \u00a0is NOT a good representation of the chair, as it misrepresents the C-C bond lengths.\u00a0<\/span><\/p>\n<p style=\"text-align: center;\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14303\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-budweiser-projection-of-cyclohexane-is-incorrect.jpg\" alt=\"F1-budweiser-projection-of-cyclohexane-is-incorrect\" width=\"275\" height=\"208\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-budweiser-projection-of-cyclohexane-is-incorrect.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-budweiser-projection-of-cyclohexane-is-incorrect-300x227.jpg 300w\" sizes=\"(max-width: 275px) 100vw, 275px\" \/><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>A Fly-by Of The Cyclohexane Chair Conformation Sometimes words just don&#8217;t do the job, so I built a model of the cyclohexane chair and took <\/p>\n","protected":false},"author":1,"featured_media":38624,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1409],"tags":[992,668,667,993,994],"post_folder":[],"class_list":["post-8174","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-conformations-cycloalkanes","tag-axial","tag-chair","tag-cyclohexane","tag-equatorial","tag-newman"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The Cyclohexane Chair Conformation: Axial, Equatorial, &quot;Up&quot; and &quot;Down&quot;<\/title>\n<meta name=\"description\" content=\"In this post we we identify &quot;axial&quot;, &quot;equatorial&quot;, &quot;up&quot; and &quot;down&quot; groups in the cyclohexane chair conformation through photos and short videos.\" \/>\n<meta name=\"robots\" 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