Enantiomer | Definition, Example, & Facts

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class="md-content"> <div class="md-article-container template-desktop"> <div class="infinite-scroll-container article last"> <article class="article-content container-lg qa-content px-0 pt-0 pb-40 py-lg-20 content " data-topic-id="186401"> <div class="grid gx-0"> <div class="col-auto"> <div class="topic-left-rail md-article-drawer position-relative d-flex border-right-sm border-left-sm open"> <div class="drawer d-flex flex-column open"> <div class="left-rail-section-content"> <div class="topic-left-rail-header text-truncate bg-gray-50 position-relative text-right d-flex align-items-center"> <div class="tlr-title px-20 py-15 text-left"> <em class="material-icons text-gray-400 d-lg-none" data-icon="toc"></em> <a class="font-serif font-weight-bold text-black link-blue" href="https://www.britannica.com/science/enantiomorph">enantiomer</a> </div> <button aria-label="Close" class="js-sections-close-button btn-link btn-sm btn d-lg-none position-absolute top-0 p-10 right-0" > <em class="material-icons font-26" data-icon="close"></em> </button> </div> <div class="section-content pl-10 pr-20 pl-sm-50 pr-sm-60 pl-lg-5 pr-lg-10 pt-10 pt-lg-0 bg-gray-50 clear-catfish-ad"> <div class="toc mb-20"> <div class="font-serif font-14 font-weight-bold mx-15 mb-15 mt-20"> Table of Contents </div> <span class="toc-extra-link selected link-gray-900 mt-15"> Introduction </span> <a class="toc-extra-link link-gray-900" href="https://www.britannica.com/science/enantiomorph/additional-info">References & Edit History</a> <a class="toc-extra-link link-gray-900" href="/facts/enantiomorph">Quick Facts & Related Topics</a> </div> <div class="tlr-media-slider pb-10 mb-30"> <a class="section-header link-gray-900 font-serif font-14 font-weight-bold mb-10 mx-10" href="https://www.britannica.com/science/enantiomorph/images-videos">Images</a> <div class="slider js-slider position-relative d-inline-flex align-items-center mw-100 "> <div class="slider-container js-slider-container overflow-hidden d-flex overflow-hidden text-nowrap ml-15"> <a href="https://cdn.britannica.com/32/125332-004-48CA8653/ball-enantiomers-hand-Analogy-reactions-hands-Label.jpg" data-href="/media/1/186401/121783" class="media-overlay-link d-inline-block mr-5"> <img loading="lazy" src="https://cdn.britannica.com/32/125332-004-48CA8653/ball-enantiomers-hand-Analogy-reactions-hands-Label.jpg" alt="Analogy between chemical reactions of enantiomers and a hand grasping a ball. If the ball is featureless, the right and left hands (enantiomers) have exactly the same interactions with the ball. However, if the ball has the word “Label” written on it and is thus a chiral object, that labeled ball will be optically active; it will mimic a single enantiomer. The left and right hands will interact differently with the labeled ball. The little finger of the right hand will approach the capital “L” of “Label” while the thumb will approach the lowercase “l.” For the left hand, the interactions will be just the opposite: the little finger will approach the lowercase “l” and the thumb the capital “L.” The figure shows these interactions, as well as a molecular counterpart in which a pair of enantiomers, (R)- and (S)-bromochlorofluoroiodomethane, interacts with a single enantiomer, (S)-2-chlorobutane. In the R enantiomer, the bromine atom approaches the methyl group (―CH3), and the iodine atom approaches the ethyl group (―CH2CH3). In the S enantiomer, the bromine atom approaches the ethyl group, and the iodine atom approaches the methyl group." height="50" /> </a> </div> <button disabled class="prev-button js-prev-button position-absolute btn btn-circle shadow btn-blue " aria-label="Previous"> <span class="material-icons md-24" data-icon="keyboard_arrow_left"></span> </button> <button disabled class="next-button js-next-button position-absolute btn btn-circle shadow btn-blue " aria-label="Next"> <span class="material-icons md-24" data-icon="keyboard_arrow_right"></span> </button> </div> </div> <div class="mb-30 tlr-related-questions"> <div class="text-gray-900 p-5 pb-0 font-serif font-14 font-weight-bold mx-10 mb-15"> Related Questions </div> <ul> <li class="link-gray-900 mb-15"><a class="" href="/question/Why-does-physics-work-in-SI-units">Why does physics work in SI units?</a> </li> <li class="link-gray-900 mb-15"><a class="" href="/question/Is-mathematics-a-physical-science">Is mathematics a physical science?</a> </li> </ul> </div> <div class="mb-30 tlr-read-next"> <div class="text-gray-900 p-5 font-serif font-14 font-weight-bold mx-10 mb-10"> Read Next </div> <div class="imagelink-with-image-on-the-side card card-horizontal tlr-img-with-side-link ml-15 link-gray-900 mb-10" > <div class="position-relative card-media" style="flex: 0;"> <a class="ilf-image position-relative" href="/story/whats-the-difference-between-speed-and-velocity"> <img loading="lazy" src="https://cdn.britannica.com/06/192806-131-75DD8878/drive-Highway-Night-Traffic-Portland-automobile-car.jpg?w=200&h=200&c=crop" alt="Highway Night Traffic Portland, drive, driving, car, automobile." width="200" height="200" /> </a> </div> <div class="card-body ilf-content"> <a class="font-weight-semi-bold d-block mb-5 font-16 ilf-title" href="/story/whats-the-difference-between-speed-and-velocity" >What's the Difference Between Speed and Velocity?</a> </div> </div> <div class="imagelink-with-image-on-the-side card card-horizontal tlr-img-with-side-link ml-15 link-gray-900 mb-10" > <div class="position-relative card-media" style="flex: 0;"> <a class="ilf-image position-relative" href="/story/gravity-from-apples-to-the-universe"> <img loading="lazy" src="https://cdn.britannica.com/85/131985-131-280FFD87/Mark-C-Lee-Extravehicular-Activity-Spacewalk-Rescue-Sept-16-1994.jpg?w=200&h=200&c=crop" alt="Above the clouds 130 nautical miles below, astronaut Mark C. 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Let us know if you have suggestions to improve this article (requires login). </div> <div class="type-menu"> <label for="feedback-type" class="label mb-10">Feedback Type</label> <select id="feedback-type" class="form-select mb-30" name="feedbackTypeId" required> <option value="" selected="selected">Select a type (Required)</option> <option value="1">Factual Correction</option> <option value="2">Spelling/Grammar Correction</option> <option value="3">Link Correction</option> <option value="4">Additional Information</option> <option value="5">Other</option> </select> </div> <label for="feedback" class="label mb-10">Your Feedback</label> <textarea id="feedback" class="form-control mb-30" name="feedback" maxlength="3000" rows="7" required></textarea> <button class="btn btn-blue" type="submit">Submit Feedback</button> </form> <div class="success-messaging d-none mt-30"> <div class="title">Thank you for your feedback</div> <p>Our editors will review what you’ve submitted and determine whether to revise the article.</p> </div> </div> </div> <div class="md-websites-modal size-lg d-none"> <div class="md-modal-body"> <div class="h2 font-serif pb-15 border-bottom font-weight-bold"> External Websites </div> <div class="pb-20"> <ul class="list-unstyled mt-20 lh-lg"> <li><a class="external" href="https://www.khanacademy.org/science/organic-chemistry/stereochemistry-topic/optical-activity/v/drawing-enantiomers" target="_blank" rel="noopener ">Khan Academy - Drawing enantiomers</a></li> <li><a class="external" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Fundamentals/Isomerism_in_Organic_Compounds/Enantiomers" target="_blank" rel="noopener ">Chemistry LibreTexts - Enantiomers</a></li> <li><a class="external" href="https://wisc.pb.unizin.org/chem109fall2021ver02/chapter/stereoisomers-enantiomers/" target="_blank" rel="noopener ">University of Wisconsin Pressbooks - Chemistry 109 Fall 2021 - Stereoisomers: Enantiomers</a></li> <li><a class="external" href="https://www.academia.edu/14976304/Safety_profile_of_enantiomers_vs_racemic_mixtures_its_the_same" target="_blank" rel="noopener ">Academia - Safety profile of enantiomers vs . racemic mixtures: it's the same?</a></li> </ul> </div> </div> </div> </div> </div> <div class="toc-header-marker"></div> <button class="ai-ask-button btn border-2 js-header-ai-ask-button d-none btn-sm btn-outline-red-400 border-red-400 mr-0 mr-lg-10 ml-5 ml-sm-10 ml-lg-0 p-10"> Ask the Chatbot a Question </button> <div class="caption alternate-titles">Also known as: antimer, enantiomorph, optical antipode</div> <div class="md-byline module-spacing "> <div class="font-serif font-12"> <span class="written-by text-gray-700"> Written and fact-checked by </span> <div class="editor-popover popover p-0"> <a class="d-block p-20 gtm-byline font-12 byline-contributor" href="/editor/The-Editors-of-Encyclopaedia-Britannica/4419" > <div class="editor-title font-16 font-weight-bold">The Editors of Encyclopaedia Britannica</div> <div class="editor-description font-12 font-serif mt-5 text-black">Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree. They write new content and verify and edit content received from contributors.</div> </a> <div data-popper-arrow></div> </div> <span class="btn btn-link editor-link p-0 qa-byline-link gtm-byline font-12 byline-contributor text-decoration-underline"> The Editors of Encyclopaedia Britannica</span></div> <div class="last-updated font-12 font-serif"> <span class="text-gray-700"> Last Updated: <time datetime="2024-10-12T00:00:00CDT" >Oct 12, 2024</time> •</span> <a class="byline-edit-history" href="https://www.britannica.com/science/enantiomorph/additional-info#history" rel="nofollow">Article History</a> </div></div> </div> <button class="d-flex d-lg-none btn btn-outline-blue border rounded-sm shadow-sm mobile-toc-button gtm-mobile-toc-inline-button d-none d-sm-block js-sections-inline-button module-spacing btn d-lg-none"> <em class="material-icons mr-5 ml-n10 my-n5 md-icon" data-icon="toc"></em> Table of Contents </button> <div class="d-flex d-sm-none flex-row"> <button class="d-flex d-lg-none btn btn-outline-blue border rounded-sm shadow-sm mobile-toc-button gtm-mobile-toc-inline-button js-sections-inline-button module-spacing"> <em class="material-icons mr-5 ml-n10 my-n5 md-icon" data-icon="toc"></em> Table of Contents </button> <button class="ai-ask-button btn border-2 ai-ask-button btn border-2 module-spacing btn-sm js-inline-ai-ask-button btn-outline-red-400 border-red-400 p-10 ml-5"> Ask the Chatbot a Question </button> </div> <div class="js-qf-module qf-module px-40 px-sm-20 py-15 mx-auto module-spacing font-14 bg-gray-50 rounded"> <div class="facts-list mt-10"> <div class=""> <div class="js-fact mb-10 line-clamp clamp-3"> <dl> <dt>Also called: </dt> <dd>enantiomorph</dd> </dl> <button class="js-more-btn d-none btn btn-unstyled font-12 bg-gray-50" aria-label="Toggle more/less fact data"> <em class="js-content link-blue">(Show more)</em> </button> </div> </div> <div class=""> <div class="js-fact mb-10 line-clamp clamp-3"> <dl> <dt>Related Topics: </dt> <dd><a href="/science/racemate" topicid="488065">racemic mixture</a></dd> <dd><a href="/science/resolution-chemistry" topicid="499358">resolution</a></dd> <dd><a href="/science/racemization" topicid="488080">racemization</a></dd> <dd><a href="/science/optical-isomerism" topicid="430441">optical isomerism</a></dd> </dl> <button class="js-more-btn d-none btn btn-unstyled font-12 bg-gray-50" aria-label="Toggle more/less fact data"> <em class="js-content link-blue">(Show more)</em> </button> </div> <div class="text-center"> <a class="btn btn-sm btn-link p-0" href="/facts/enantiomorph"> See all related content </a> </div> </div> </div> </div><span class="marker before-article"></span><section data-level="1" id="ref1"><span class="marker PREMOD1 mod-inline"></span><p class="topic-paragraph"><strong><span id="ref70869"></span>enantiomer</strong>, either of a pair of objects related to each other as the right hand is to the left—that is, as mirror images that cannot be reoriented so as to appear identical. An object that has a plane of <a class="md-dictionary-link md-dictionary-tt-off eb" data-term="symmetry" href="https://www.britannica.com/dictionary/symmetry" data-type="EB">symmetry</a> cannot be an enantiomer because the object and its mirror image are identical. Molecular enantiomers, such as those of <span id="ref70870"></span><a href="https://www.britannica.com/science/lactic-acid" class="md-crosslink " data-show-preview="true">lactic acid</a>, have identical chemical properties, except in their <a href="https://www.britannica.com/science/chemical-reaction" class="md-crosslink " data-show-preview="true">chemical reaction</a> with other dissymmetric <a href="https://www.britannica.com/science/molecule" class="md-crosslink " data-show-preview="true">molecules</a> and with polarized light. Enantiomers are important to <span id="ref70871"></span><a href="https://www.britannica.com/science/crystal" class="md-crosslink " data-show-preview="true">crystallography</a> because many <a href="https://www.britannica.com/science/crystal" class="md-crosslink " data-show-preview="true">crystals</a> are arrangements of alternate right- and left-handed forms of a single molecule. A complete description of the crystal specifies how the forms are mixed with each other.</p><span class="marker MOD1 mod-inline"></span><span class="marker PREMOD2 mod-inline"></span><p class="topic-paragraph">An example of a pair of substances that are enantiomers is the two optically active forms of <span id="ref70872"></span><a href="https://www.britannica.com/science/tartaric-acid" class="md-crosslink " data-show-preview="true">tartaric acid</a>, designated as <em>d</em>-tartaric acid and <em>l</em>-tartaric acid. The <a class="md-dictionary-link md-dictionary-tt-off eb" data-term="configurations" href="https://www.britannica.com/dictionary/configurations" data-type="EB">configurations</a> of the individual molecules of these two substances have been shown to be mirror images of one another, as represented by the following projection formulas:<span class="md-formula"><span id="ref-15894"></span><img src="https://cdn.britannica.com/94/15894-004-1086D04B/Structures-acids.jpg" alt="Structures of d- and l-tartaric acids." class="inline-image-baseline"></span></p><div class="one-good-fact-module"> </div><span class="marker MOD2 mod-inline"></span><span class="marker PREMOD3 mod-inline"></span><p class="topic-paragraph">The two acids have identical <a href="https://www.britannica.com/science/melting-point" class="md-crosslink " data-show-preview="true">melting points</a>, <a href="https://www.britannica.com/science/density" class="md-crosslink " data-show-preview="true">densities</a>, and <a href="https://www.britannica.com/science/solubility-chemistry" class="md-crosslink " data-show-preview="true">solubilities</a> in optically inactive <a href="https://www.britannica.com/science/solvent-chemistry" class="md-crosslink " data-show-preview="true">solvents</a> and the same rates of reactions with optically inactive reagents.</p><a class="link-module shadow-sm d-block qa-read-more-module" href="/science/isomerism/Enantiomers#ref1015111" data-link-module-iframe-link=""> <img loading="lazy" src="https://cdn.britannica.com/11/7411-050-58FE3D05/geometry-methane-model-distances-bond-angles.jpg" alt="chemical structure of methane" class="rounded-sm mr-15" width="70" /> <div class="line-clamp clamp-5"> <div class="module-title bg-navy-dark">More From Britannica</div> <div class="font-weight-semi-bold mt-5">isomerism: Enantiomers</div> </div> </a><span class="marker MOD3 mod-inline"></span></section> <span class="md-signature"><a href="/editor/The-Editors-of-Encyclopaedia-Britannica/4419">The Editors of Encyclopaedia Britannica</a></span><span class="md-signature">This article was most recently revised and updated by <a href="/editor/Erik-Gregersen/6723">Erik Gregersen</a>.</span><span class="marker end-of-content"></span><span class="marker after-article"></span></div> <div id="chatbot-root"></div> </div> </div> </div> <div class="ai-dialog-placeholder"></div> </div> </div> <aside class="col-md-da-320"></aside> </div> </div> </div> </div> </article></div> </div></div> </div> </main> <div id="md-footer"></div> <noscript><iframe src="//www.googletagmanager.com/ns.html?id=GTM-5W6NC8" height="0" width="0" style="display:none;visibility:hidden"></iframe></noscript> <script type="text/javascript" id="_informizely_script_tag"> var IzWidget = IzWidget || {}; 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Enantiomer | Definition, Example, & Facts | Britannica