I'd like you to ask yourself, what do you feel when you hear the words "organic chemistry?" What comes to mind?
我想请各位问问自己，听到“有机化学”时，你有什么感觉？会想到什么？
There is a course offered at nearly every university, and it's called Organic Chemistry,
几乎在每一所大学都有开一门课程，就叫做“有机化学”，
and it is a grueling, heavy introduction to the subject, a flood of content that overwhelms students,
这门课是种既繁重又累人的有机化学入门，一大堆的内容，让学生无法招架，
and you have to ace it if you want to become a doctor or a dentist or a veterinarian.
如果你想要成为医生、牙医或兽医，就得要把这门课读好。
And that is why so many students perceive this science like this ... as an obstacle in their path,
那就是为什么很多学生都这样看待这门科学……他们道路上的阻碍，
and they fear it and they hate it and they call it a weed-out course.
他们害怕它、讨厌它，他们称它为一门淘汰课。
What a cruel thing for a subject to do to young people, weed them out.
一门学科对年轻人做这样的事，实在很残忍，把他们淘汰。
And this perception spread beyond college campuses long ago. There is a universal anxiety about these two words.
很早以前，这种感受就已经散播到大学校园以外的地方了。不论在哪里，这四个字都让人焦虑。
I happen to love this science, and I think this position in which we have placed it is inexcusable.
我刚好很爱这门科学，我认为，我们将它定位在这个位置，实在不可原谅。
It's not good for science, and it's not good for society, and I don't think it has to be this way.
那样对科学没有好处，对社会没有好处，我不认为这是必要的。
And I don't mean that this class should be easier. It shouldn't.
我的意思并不是这门课应该简单一点。它不该简单。
But your perception of these two words should not be defined by the experiences of premed students
但你们对于这四个字的感受不应该被医学院预科学生的经验所定义，
who frankly are going through a very anxious time of their lives.
坦白说，他们正在经历 他们人生中非常焦虑的时期。
So I'm here today because I believe that a basic knowledge of organic chemistry is valuable,
今天我来这里，是因为我相信有机化学的基本知识是很有价值的，
and I think that it can be made accessible to everybody, and I'd like to prove that to you today. Would you let me try? Yeah!
我认为它应该是任何人都可以进入的一门科学，今天我会向大家证明这一点。你们愿意让我试试吗？愿意！
All right, let's go for it.
好，咱们开始吧！
Here I have one of these overpriced EpiPens. Inside it is a drug called epinephrine.
我手上是一支定价过高的肾上腺素注射器。里面装的是一种叫肾上腺素的药。
Epinephrine can restart the beat of my heart, or it could stop a life-threatening allergic reaction.
肾上腺素能够让我的心脏重新开始跳动，它也可以阻止可能威胁生命的过敏反应。
An injection of this right here will do it.
只要把它注射到这里就可以了。
It would be like turning the ignition switch in my body's fight-or-flight machinery.
它就像是一个点火开关，控制我身体的“打或逃”机械装置。
My heart rate, my blood pressure would go up so blood could rush to my muscles.
我的心率、我的血压会上升，血液就会被急送给我的肌肉。
My pupils would dilate. I would feel a wave of strength.
我的瞳孔会放大。我会感受到一波力量。
Epinephrine has been the difference between life and death for many people.
对许多人而言，肾上腺素决定了他们是生还是死。
This is like a little miracle that you can hold in your fingers.
它就像是你能够掌握在手中的一个小小奇迹。
Here is the chemical structure of epinephrine. This is what organic chemistry looks like.
这是肾上腺素的化学结构。有机化学看起来就是这个样子的。
It looks like lines and letters ... No meaning to most people.
它看起来像是线段和英文字母……对大部分人来说没有意义。
I'd like to show you what I see when I look at that picture.
我想展示一下当看到这张图时我看见的是什么。
I see a physical object that has depth and rotating parts, and it's moving.
我看见一个实体的物体，有立体深度，也有能旋转的部位，且它会动。
We call this a compound or a molecule, and it is 26 atoms that are stitched together by atomic bonds.
我们称它为化合物或分子，它是由26个原子，用原子键结合在一起而成。
The unique arrangement of these atoms gives epinephrine its identity,
这些原子的独特排列方式，就代表着肾上腺素，
but nobody has ever actually seen one of these, because they're very small,
但没有人看见过这些东西，因为它们非常小，
so we're going to call this an artistic impression, and I want to explain to you how small this is.
所以我们可以称它为艺术印象，我想要跟各位说明它有多小。
In here, I have less than half a milligram of it dissolved in water. It's the mass of a grain of sand.
在这里，我取了半毫克，将它溶解在水中。这是一粒沙的质量。
The number of epinephrine molecules in here is one quintillion.
这里的肾上腺素分子数量是一百万的三次方。
That's 18 zeroes. That number is hard to visualize.
也就是18个零。这个数字很难可视化。
Seven billion of us on this planet? Maybe 400 billion stars in our galaxy? You're not even close.
在地球上有70亿人？宇宙中也许有4000亿颗星星？都还差得远呢。
If you wanted to get into the right ballpark, you'd have to imagine every grain of sand on every beach, under all the oceans and lakes,
如果你想要做更正确的约略估计，你得要想象在所有海洋和湖泊底下，每一个海滩上的每一粒沙子，
and then shrink them all so they fit in here.
接着把它们通通缩小，塞到这里面来。
Epinephrine is so small we will never see it, not through any microscope ever, but we know what it looks like,
肾上腺素非常小，我们永远不可能看见它，透过任何显微镜都不可能，但我们知道它的外观，
because it shows itself through some sophisticated machines with fancy names like "nuclear magnetic resonance spectrometers."
因为它能透过一些很精密的机器显现出来，这些机器的名字很炫，比如“核磁共振光谱仪”。
So visible or not, we know this molecule very well.
不论看不看得见，我们都很了解这个分子。
We know it is made of four different types of atoms, hydrogen, carbon, oxygen and nitrogen.
我们知道它是由四种不同型的原子组成，氢、碳、氧和氮。
These are the colors we typically use for them. Everything in our universe is made of little spheres that we call atoms.
我们通常会用这些颜色来表示它们。在我们宇宙中的一切，都是由小球体组成，它们叫做原子。
There's about a hundred of these basic ingredients,
这种基本组成元素大约有100种，
and they're all made from three smaller particles: protons, neutrons, electrons
它们都是用这三种更小的粒子组成的：光子、中子、电子。
We arrange these atoms into this familiar table. We give them each a name and a number.
我们用这个熟悉的表格来排放这些原子。每一种都有一个名称和数字。
But life as we know it doesn't need all of these, just a smaller subset, just these.
但我们所知道的生命，并不需要表中的每一种原子，只需要其中的一些，只要这些即可。
And there are four atoms in particular that stand apart from the rest as the main building blocks of life,
有四种原子很特别，和其他原子不同，它们是生建造生命的主要建材，
and they are the same ones that are found in epinephrine: hydrogen, carbon, nitrogen and oxygen.
也就是在肾上腺素中找到的那几种：氢、碳、氮以及氧。
Now what I tell you next is the most important part.
我接下来要告诉各位的是最重要的部分。
When these atoms connect to form molecules, they follow a set of rules.
当这些原子连结起来形成分子，它们会遵循一组规则。
Hydrogen makes one bond, oxygen always makes two, nitrogen makes three and carbon makes four. That's it.
氢有一个键结，氧总是有两个键结，氮有三个键结，碳有四个键结。就这样。
HONC -- one, two, three, four. If you can count to four, and you can misspell the word "honk,"
H、O、N、C，一、二、三、四。如果你会数到四，且你会拼错“honk（喇叭声）”这个字，
you're going to remember this for the rest of your lives.
那你一辈子就不会忘记这些。
Now here I have four bowls with these ingredients.
这里，我有四个碗，里面有这些组成元素。
We can use these to build molecules. Let's start with epinephrine.
我们可以用它们来建立分子。咱们从肾上腺素开始。
Now, these bonds between atoms, they're made of electrons.
在原子之间的键结是由电子组成的。
Atoms use electrons like arms to reach out and hold their neighbors.
原子把电子当成手臂来用，向外伸，抓住它们的邻居。
Two electrons in each bond, like a handshake, and like a handshake, they are not permanent.
每个键结有两个电子，就像在握手，还有一点也像握手：它们并非永久的。
They can let go of one atom and grab another.
它们会放掉一个原子，去抓另一个。
That's what we call a chemical reaction, when atoms exchange partners and make new molecules.
那就是我们所谓的化学反应，原子会交换伙伴，并形成新分子。
The backbone of epinephrine is made mostly of carbon atoms, and that's common.
肾上腺素的主要骨干大部分是由碳原子所组成，那很常见。
Carbon is life's favorite structural building material,
碳是生命最喜欢的结构建材，
because it makes a good number of handshakes with just the right grip strength.
因为它握手的数量很理想，握手的力量也很恰好。
That's why we define organic chemistry as the study of carbon molecules.
那就是为什么我们把有机化学定义为对碳原子的研究。
Now, if we build the smallest molecules we can think of that follow our rules,
如果我们依据我们的规则，建造出我们所能想出最小的分子，
they highlight our rules, and they have familiar names: water, ammonia and methane, H20 and NH3 and CH4.
它们会突显出我们的规则，并且它们的名字都很耳熟：水、氨、甲烷，即H2O、NH3和CH4。
The words "hydrogen," "oxygen" and "nitrogen" -- we use the same words to name these three molecules that have two atoms each.
“氢”、“氧”和“氮”这些字--这三个分子都各含有两个相同的原子，所以我们直接以原子的名字来命名它们。
They still follow the rules, because they have one, two and three bonds between them. That's why oxygen gets called O2.
它们仍然遵循规则，因为它们之间的键结数为一、二以及三个。那就是为什么氧气要叫O2。
I can show you combustion. Here's carbon dioxide, CO2.
我可以展示燃烧给各位看。这是二氧化碳，CO2。
Above it, let's place water and oxygen, and beside it, some flammable fuels.
在上面，我们放上水和氧，在旁边，是可燃的燃料。
These fuels are made of just hydrogen and carbon. That's why we call them hydrocarbons. We're very creative.
这些燃料的成份只有氢和碳。所以它们被称为碳氢化合物。我们很有创意。
So when these crash into molecules of oxygen, as they do in your engine or in your barbecues,
当这些分子撞上氧分子，就像在引擎或烤肉野餐所发生的状况，
they release energy and they reassemble, and every carbon atom ends up at the center of a CO2 molecule,
它们就会释出能量、重组，每个碳原子最后都会成为一个CO2分子的中心，
holding on to two oxygens, and all the hydrogens end up as parts of waters, and everybody follows the rules.
抓住两个氧原子，所有的氢最后都会成为水的一部分，大家都会遵循规则。
They are not optional, and they're not optional for bigger molecules either, like these three.
没得选，更大的分子也没得选，比如这三个分子。
This is our favorite vitamin sitting next to our favorite drug,
这是我们最爱的维他命，旁边是我们最爱的药物，
and morphine is one of the most important stories in medical history.
在医疗史上，吗啡是最重要的故事之一。
It marks medicine's first real triumph over physical pain, and every molecule has a story, and they are all published.
它代表的是医学第一次战胜了身体的痛苦，每个分子都有一段故事，通通都已经出版。
They're written by scientists, and they're read by other scientists,
这些故事是由科学家所写，读者则是其他科学家，
so we have handy representations to do this quickly on paper, and I need to teach you how to do that.
所以，我们有方便的表示方式，方便论文的读写，而我得要教各位这些表示方式。

So we lay epinephrine flat on a page, and then we replace all the spheres with simple letters,
我们把肾上腺素摊平放在一张纸上，接着，我们把所有的球体都换成简单的字母，
and then the bonds that lie in the plane of the page, they just become regular lines,
再把平面纸上的那些键结也换掉，换成一般的线段，
and the bonds that point forwards and backwards, they become little triangles, either solid or dashed to indicate depth.
至于指向前以及向后的那些键结，就换成小三角形，用实心或是虚线来呈现深度。
We don't actually draw these carbons. We save time by just hiding them.
我们不会真的画出这些碳。为了节省时间，我们会把它们隐藏起来。
They're represented by corners between the bonds, and we also hide every hydrogen that's bonded to a carbon.
键结之间的转角，就表示碳，我们也会把和碳连结的氢给隐藏起来。
We know they're there whenever a carbon is showing us any fewer than four bonds.
我们只要看到一个碳旁边的键结不到四个，就知道有氢在那里。
The last thing that's done is the bonds between OH and NH.
最后处理的是OH和NH间的键结。
We just get rid of those to make it cleaner, and that's all there is to it.
我们直接把它们拿掉，让画面更干净，就只有这样而已。
This is the professional way to draw molecules. This is what you see on Wikipedia pages.
这是画分子的专业方法。在维基百科上看到的图就是这种图。
It takes a little bit of practice, but I think everyone here could do it, but for today, this is epinephrine.
需要一点练习，但我认为这里人人都做得到，但今天，知道这是肾上腺素即可。
This is also called adrenaline. They're one and the same. It's made by your adrenal glands.
epinephrine和adrenaline这两个字都是指肾上腺素。它是由你的肾上腺制造的。
You have this molecule swimming through your body right now. It's a natural molecule.
现在你的体内就有这种分子在游动。它是种天然分子。
This EpiPen would just give you a quick quintillion more of them.
这支肾上腺素注射器只是很快地再补给十的十八次方个给你。
We can extract epinephrine from the adrenal glands of sheep or cattle, but that's not where this stuff comes from.
我们可以从羊或牛的肾上腺抽取出肾上腺素，但我手上的这东西并不是这么来的。
We make this epinephrine in a factory by stitching together smaller molecules that come mostly from petroleum.
这种肾上腺素是在工厂制造的，做法是把比较小的分子结合起来，而这些分子通常都来自石油。
And this is 100 percent synthetic. And that word, "synthetic," makes some of us uncomfortable.
这是100%合成的。“合成”这个词会让一些人感到不舒服。
It's not like the word "natural," which makes us feel safe.
它不像是“天然”这个词会让我们感到安全。
But these two molecules, they cannot be distinguished.
但这两种分子其实完全一样，无法区别。
We're not talking about two cars that are coming off an assembly line here.
我们并不是在谈同一条生产在线产出的两台车。
A car can have a scratch on it, and you can't scratch an atom.
车体上可能会有刮痕，你无法去刮一个原子。
These two are identical in a surreal, almost mathematical sense.
在一种超现实，几乎可说是数学的意义上，这两种分子是一样的。
At this atomic scale, math practically touches reality. And a molecule of epinephrine ... it has no memory of its origin.
在原子的尺度上，数学几乎是切中现实的。而肾上腺素的分子--它不会记着它的来源。
It just is what it is, and once you have it, the words "natural" and "synthetic," they don't matter,
它就是它，一旦你有了它，是“天然”或“合成”都无所谓了，
and nature synthesizes this molecule just like we do, except nature is much better at this than we are.
并且大自然和我们用同样的方式合成这种分子，只差在大自然比我们更擅常这件事。
Before there was life on earth, all the molecules were small, simple: carbon dioxide, water, nitrogen, just simple things.
在地球上有生命出现之前，所有的分子都很小、很简单：二氧化碳、水、氮，都是简单的东西。
The emergence of life changed that. Life brought biosynthetic factories that are powered by sunlight,
生命的出现带来了改变。生命带来了生物合成工厂，靠太阳能提供能量，
and inside these factories, small molecules crash into each other and become large ones:
在这些工厂内，小分子会发生碰撞，变成较大的分子：
carbohydrates, proteins, nucleic acids, multitudes of spectacular creations.
碳氢化合物、蛋白质、核酸，许许多多了不起的创造物。
Nature is the original organic chemist, and her construction also fills our sky with the oxygen gas we breathe, this high-energy oxygen.
大自然是最原始的有机化学家，靠它的建造，我们的天空中才会充满了我们呼吸的氧气，这种高能的氧。
All of these molecules are infused with the energy of the sun.
太阳的能量会注入所有这些分子之中。
They store it like batteries. So nature is made of chemicals.
存在分子之中，就像电池。所以，大自然是由化学物质组成的。
Maybe you guys can help me to reclaim this word, "chemical," because it has been stolen from us.
也许各位可以协助我恢复“化学”这个词的意思，因为它被从我们身上偷走了。
It doesn't mean toxic, and it doesn't mean harmful, and it doesn't mean man-made or unnatural. It just means "stuff," OK?
它并不是指有毒，不是指有害，它也不是指人造的或非自然的。它的意思就只是“原料”，好吗？
You can't have chemical-free lump charcoal. That is ridiculous.
不可能会有任何木炭块是没有化学物质的。那太荒谬了。
And I'd like to do one more word. The word "natural" doesn't mean "safe," and you all know that.
我还想再谈一个词。“天然”这个词并不表示“安全”，你们都知道这一点。
Plenty of nature's chemicals are quite toxic, and others are delicious, and some are both ... toxic and delicious.
很多大自然的化学物质是相当毒的，有些则是很可口，有些两者都是……又毒又可口。
The only way to tell whether something is harmful is to test it, and I don't mean you guys.
只有一种方式可以分辨一样东西是否有害，就是去测试它，我不是指在座各位。
Professional toxicologists: we have these people. They're well-trained, and you should trust them like I do.
专业毒物学家：有这种人存在。他们受过很好的训练，你们应该跟我一样相信他们。
So nature's molecules are everywhere, including the ones that have decomposed into these black mixtures that we call petroleum.
所以，大自然的分子无所不在，其中有些分子，已经分解成这种被我们称为石油的黑色混合物。
We refine these molecules. There's nothing unnatural about them. We purify them.
我们精炼这些分子。这么做一点也不会“不天然”。我们将它们纯化。
Now, our dependence on them for energy -- that means that every one of those carbons gets converted into a molecule of CO2.
在能源方面，我们要依赖它们--那就表示，那些碳全部都会被转换成CO2分子。
That's a greenhouse gas that is messing up our climate.
那是一种温室气体，会扰乱我们的气候。
Maybe knowing this chemistry will make that reality easier to accept for some people, I don't know,
也许对一些人而言，知道这种化学特性，会比较容易接受现实，我不知道，
but these molecules are not just fossil fuels.
但这些分子并不只是化石燃料。
They're also the cheapest available raw materials for doing something that we call synthesis.
要做合成时，它们也是可得原料当中最便宜的。
We're using them like pieces of LEGO. We have learned how to connect them or break them apart with great control.
我们把它们当成乐高积木来使用。我们已经学会如何连结它们或在得宜的掌控下将它们拆解。
I have done a lot of this myself, and I still think it's amazing it's even possible.
我自己就常常这么做，我仍然觉得能做到这样真的很了不起。
What we do is kind of like assembling LEGO by dumping boxes of it into washing machines, but it works.
我们所做的，就像是组合乐高积木，但做法是把整盒积木倒到洗衣机里面，但这样是可行的。
We can make molecules that are exact copies of nature, like epinephrine,
我们能做出和天然分子一样的分子，就像肾上腺素，
or we can make creations of our own from scratch, like these two.
或者我们也可以自己从无到有来创造，就像这两种。
One of these eases the symptoms of multiple sclerosis; the other one cures a type of blood cancer that we call T-cell lymphoma.
其中一种可以缓和多发性硬化的症状；另一种可以治疗一种血癌，叫做T细胞淋巴瘤。
A molecule with the right size and shape, it's like a key in a lock,
大小和形状正确的分子，就像是一把锁的钥匙，
and when it fits, it interferes with the chemistry of a disease. That's how drugs work.
如果能对上，它就能干涉疾病的化学性质。药品就是这么运作的。
Natural or synthetic, they're all just molecules that happen to fit snugly somewhere important.
不论是天然的或合成的，它们都只是在重要的地方刚好完全符合需求的分子。
But nature is much better at making them than we are, so hers look more impressive than ours, like this one.
但大自然远比我们更擅长制造它们，所以她的成品比我们的更让人印象深刻，就像这一个。
This is called vancomycin. She gave this majestic beast two chlorine atoms to wear like a pair of earrings.
它叫做万古霉素。大自然给予这只雄伟的巨兽两个氯原子，就像戴着耳环一样。
We found vancomycin in a puddle of mud in a jungle in Borneo in 1953.
1953年，我们在婆罗洲的丛林中的一个泥坑里发现了万古霉素。
It's made by a bacteria. We can't synthesize this cost-efficiently in a lab.
它是由细菌制造的。在实验室中，我们没有高成本效益的方式来合成它。
It's too complicated for us, but we can harvest it from its natural source,
对我们来说，它太复杂了，但我们可以从它的天然来源取得它，
and we do, because this is one of our most powerful antibiotics.
我们确实这么做了，因为它是我们最强大的抗生素之一。
And new molecules are reported in our literature every day.
每天在我们的文献中都会有新分子的信息。
We make them or we find them in every corner of this planet.
我们制造新分子，或在地球上的每个角落寻找新分子。
And that's where drugs come from, and that's why your doctors have amazing powers to cure deadly infections and everything else.
药品就是这么来的，那就是为什么医生有很了不起的力量……来治疗会致命的感染及其他病症。
Being a physician today is like being a knight in shining armor.
现今，身为医生就像是身为穿着闪亮盔甲的骑士。
They fight battles with courage and composure, but also with good equipment.
他们带着勇气和和沉着去作战，但也有很好的装备。
So let's not forget the role of the blacksmith in this picture,
别忘了在这张图片中铁匠所扮演的角色，
because without the blacksmith, things would look a little different ...
因为若没有铁匠，一切看起来就会有点不同……
But this science is bigger than medicine.
但这项科学不只是医学。
It is oils and solvents and flavors, fabrics, all plastics, the cushions that you're sitting on right now
它也是石油、溶剂、味道、织物、所有的塑料。各位现在所坐的坐垫，
they're all manufactured, and they're mostly carbon, so that makes all of it organic chemistry. This is a rich science.
都是制造来的，它们大部分是碳，所以它们都是有机化学。它是一项丰富的科学。
I left out a lot today: phosphorus and sulfur and the other atoms,
今天我省去了很多：磷和硫以及其他原子，
and why they all bond the way they do, and symmetry and non-bonding electrons, and atoms that are charged,
以及它们的键结方式为什么是那样的，还有对称性，以及没有键结的电子，还有被充电的原子，
and reactions and their mechanisms, and it goes on and on and on, and synthesis takes a long time to learn.
以及反应和它们的机制，还有好多好多，合成需要花很多时间去学。
But I didn't come here to teach you guys organic chemistry -- I just wanted to show it to you,
但我并不是来这里教各位有机化学的--我只是想将它展示给各位看，
and I had a lot of help with that today from a young man named Weston Durland, and you've already seen him.
且一位叫做威斯顿·德兰的年轻人给了我很大的协助，你们已经看过他了。
He's an undergraduate student in chemistry, and he also happens to be pretty good with computer graphics.
他是化学系的大学生，他刚好也非常擅长计算机绘图。
So Weston designed all the moving molecules that you saw today.
今天各位看到所有会动的原子都是威斯顿设计的。
He and I wanted to demonstrate through the use of graphics like these to help someone talk about this intricate science.
我和他想要用这样的绘图来做展示，来协助讲解这门复杂的科学。
But our main goal was just to show you that organic chemistry is not something to be afraid of.
但我们主要的目标只是要让各位看到，没有必要害怕有机化学。
It is, at its core, a window through which the beauty of the natural world looks richer. Thank you.
它在本质上就是一扇窗，通过它，自然世界的美好看起来会更丰富。谢谢。