what do you feel when you hear the words "organic chemistry?"

我想請各位問問自己，

What comes to mind?

聽到「有機化學」時， 你有什麼感覺？

There is a course offered at nearly every university,

會想到什麼？

and it's called Organic Chemistry,

幾乎在每一所大學， 都有開一門課程，

and it is a grueling, heavy introduction to the subject,

就叫做「有機化學」，

a flood of content that overwhelms students,

這門課是種既繁重又累人的 有機化學入門，

and you have to ace it if you want to become a doctor or a dentist

一大堆的內容，讓學生無法招架，

or a veterinarian.

如果你想要成為醫生、 牙醫，或獸醫，

And that is why so many students perceive this science like this ...

就得要把這門課讀好。

as an obstacle in their path,

那就是為什麼很多學生 都這樣看待這門科學……

and they fear it and they hate it

他們道路上的阻礙，

and they call it a weed-out course.

他們害怕它、討厭它，

What a cruel thing for a subject to do to young people,

他們稱它為一門淘汰課。

weed them out.

一門學科對年輕人 做這樣的事，實在很殘忍，

And this perception spread beyond college campuses long ago.

把他們淘汰。

There is a universal anxiety about these two words.

很早以前，這種感受就已經 散播到大學校園以外的地方了。

I happen to love this science,

不論在哪裡， 這四個字都讓人焦慮。

and I think this position in which we have placed it

我剛好很愛這門科學，

is inexcusable.

我認為，我們將它 定位在這個位置，

It's not good for science, and it's not good for society,

實在不可原諒。

and I don't think it has to be this way.

那樣對科學沒有好處， 對社會沒有好處，

And I don't mean that this class should be easier. It shouldn't.

我不認為這是必要的。

But your perception of these two words

我的意思並不是這門課 應該簡單一點。它不該簡單。

should not be defined by the experiences of premed students

但你們對於這四個字的感受

who frankly are going through a very anxious time of their lives.

不應該被醫學院預科 學生的經驗所定義，

So I'm here today because I believe

坦白說，他們正在經歷 他們人生中非常焦慮的時期。

that a basic knowledge of organic chemistry is valuable,

今天，我來這裡，是因為我相信

and I think that it can be made accessible to everybody,

有機化學的基本知識 是很有價值的，

and I'd like to prove that to you today.

我認為它應該是任何人 都可以進入的一門科學，

Would you let me try?

今天我會向大家證明這一點。

Audience: Yeah!

你們願意讓我試試嗎？

Jakob Magolan: All right, let's go for it.

觀眾：願意！

(Laughter)

講者：好，咱們開始吧！

Here I have one of these overpriced EpiPens.

（笑聲）

Inside it is a drug called epinephrine.

我手上是一支定價過高的 腎上腺素注射器。

Epinephrine can restart the beat of my heart,

裡面裝的是一種叫腎上腺素的藥。

or it could stop a life-threatening allergic reaction.

腎上腺素能夠讓我的心臟 重新開始跳動，

An injection of this right here will do it.

它也可以阻止可能 威脅生命的過敏反應。

It would be like turning the ignition switch

只要把它注射到這裡就可以了。

in my body's fight-or-flight machinery.

它就像是一個點火開關，

My heart rate, my blood pressure would go up so blood could rush to my muscles.

控制我身體的 「打或逃」機械裝置。

My pupils would dilate. I would feel a wave of strength.

我的心跳率、我的血壓會上升， 血液就會被急送給我的肌肉。

Epinephrine has been the difference between life and death for many people.

我的瞳孔會放大。 我會感受到一波力量。

This is like a little miracle that you can hold in your fingers.

對許多人而言，腎上腺素 決定了他們是生還是死。

Here is the chemical structure of epinephrine.

它就像是你能夠掌握 在手中的一個小小奇蹟。

This is what organic chemistry looks like.

這是腎上腺素的化學結構。

It looks like lines and letters ...

有機化學看起來就是這個樣子的。

No meaning to most people.

它看起來像是線段和英文字母……

I'd like to show you what I see when I look at that picture.

對大部分人來說沒有意義。

I see a physical object

我想展示一下，當看到 這張圖時我看見的是什麼。

that has depth and rotating parts,

我看見一個實體的物體，

and it's moving.

有立體深度，也有能旋轉的部位，

We call this a compound or a molecule,

且它會動。

and it is 26 atoms that are stitched together by atomic bonds.

我們稱它為化合物或分子，

The unique arrangement of these atoms gives epinephrine its identity,

它是由 26 個原子， 用原子鍵結合在一起而成。

but nobody has ever actually seen one of these,

這些原子的獨特排列方式， 就代表著腎上腺素，

because they're very small,

但沒有人看見過這些東西，

so we're going to call this an artistic impression,

因為它們非常小，

and I want to explain to you how small this is.

所以我們可以稱它為藝術印象，

In here, I have less than half a milligram of it dissolved in water.

我想要跟各位說明它有多小。

It's the mass of a grain of sand.

在這裡，我取了半毫克， 將它溶解在水中。

The number of epinephrine molecules in here is one quintillion.

這是一粒沙的質量。

That's 18 zeroes.

這裡的腎上腺素分子數量 是一百萬的三次方。

That number is hard to visualize.

也就是 18 個零。

Seven billion of us on this planet?

這個數字很難視覺化。

Maybe 400 billion stars in our galaxy?

在地球上有 70 億人？

You're not even close.

宇宙中也許有 4000 億顆星星？

If you wanted to get into the right ballpark,

都還差得遠呢。

you'd have to imagine every grain of sand

如果你想要做更正確的約略估計，

on every beach, under all the oceans and lakes,

你得要想像在所有 海洋和湖泊底下，

and then shrink them all so they fit in here.

每一個海灘上的每一粒沙子，

Epinephrine is so small we will never see it,

接著把它們通通縮小， 塞到這裡面來。

not through any microscope ever,

腎上腺素非常小， 我們永遠不可能看見它，

but we know what it looks like,

透過任何顯微鏡都不可能，

because it shows itself through some sophisticated machines

但我們知道它的外觀，

with fancy names

因為它能透過一些 很精密的機器顯現出來，

like "nuclear magnetic resonance spectrometers."

這些機器的名字很炫，

So visible or not, we know this molecule very well.

比如「核磁共振光譜儀」。

We know it is made of four different types of atoms,

不論看不看得見， 我們都很了解這個分子。

hydrogen, carbon, oxygen and nitrogen.

我們知道它是由四種 不同型的原子組成，

These are the colors we typically use for them.

氫、碳、氧，和氮。

Everything in our universe is made of little spheres

我們通常會用 這些顏色來表示它們。

that we call atoms.

在我們宇宙中的一切， 都是由小球體組成，

There's about a hundred of these basic ingredients,

它們叫做原子。

and they're all made from three smaller particles:

這種基本組成元素大約有 100 種，

protons, neutrons, electrons.

它們都是用這三種 更小的粒子組成的：

We arrange these atoms into this familiar table.

光子、中子、電子。

We give them each a name and a number.

我們用這個熟悉的表格 來排放這些原子。

But life as we know it doesn't need all of these,

每一種都有一個名稱和數字。

just a smaller subset, just these.

但我們所知道的生命， 並不需要表中的每一種原子，

And there are four atoms in particular that stand apart from the rest

只需要其中的一些， 只要這些即可。

as the main building blocks of life,

有四種原子很特別， 和其他原子不同，

and they are the same ones that are found in epinephrine:

它們是生建造生命的主要建材，

hydrogen, carbon, nitrogen and oxygen.

也就是在腎上腺素中 找到的那幾種：

Now what I tell you next is the most important part.

氫、碳、氮，以及氧。

When these atoms connect to form molecules,

我接下來要告訴各位的， 是最重要的部分。

they follow a set of rules.

當這些原子連結起來，形成分子，

Hydrogen makes one bond,

它們會遵循一組規則。

oxygen always makes two,

氫有一個鍵結，

nitrogen makes three

氧總是有兩個鍵結，

and carbon makes four.

氮有三個鍵結，

That's it.

碳有四個鍵結。

HONC -- one, two, three, four.

就這樣。

If you can count to four, and you can misspell the word "honk,"

H、O、N、C，一、二、三、四。

you're going to remember this for the rest of your lives.

如果你會數到四，且你會拼錯 「honk（喇叭聲）」這個字，

(Laughter)

那你一輩子就不會忘記這些。

Now here I have four bowls with these ingredients.

（笑聲）

We can use these to build molecules.

這裡，我有四個碗， 裡面有這些組成元素。

Let's start with epinephrine.

我們可以用它們來建立分子。

Now, these bonds between atoms, they're made of electrons.

咱們從腎上腺素開始。

Atoms use electrons like arms to reach out and hold their neighbors.

在原子之間的鍵結， 是由電子組成的。

Two electrons in each bond, like a handshake,

原子把電子當成手臂來用， 向外伸，抓住它們的鄰居。

and like a handshake, they are not permanent.

每個鍵結有兩個電子， 就像在握手，

They can let go of one atom and grab another.

還有一點也像握手： 它們並非永久的。

That's what we call a chemical reaction,

它們會放掉一個原子， 去抓另一個。

when atoms exchange partners and make new molecules.

那就是我們所謂的化學反應，

The backbone of epinephrine is made mostly of carbon atoms,

原子會交換夥伴，並形成新分子。

and that's common.

腎上腺素的主要骨幹 大部分是由碳原子所組成，

Carbon is life's favorite structural building material,

那很常見。

because it makes a good number of handshakes

碳是生命最喜歡的結構建材，

with just the right grip strength.

因為它握手的數量很理想，

That's why we define organic chemistry as the study of carbon molecules.

握手的力量也很恰好。

Now, if we build the smallest molecules we can think of that follow our rules,

那就是為什麼我們把有機化學 定義為對碳原子的研究。

they highlight our rules, and they have familiar names:

如果我們依據我們的規則， 建造出我們所能想出最小的分子，

water, ammonia and methane, H20 and NH3 and CH4.

它們會突顯出我們的規則， 且它們的名字都很耳熟：

The words "hydrogen," "oxygen" and "nitrogen" --

水、氨、甲烷， 即 H2O、NH3，和 CH4。

we use the same words

「氫」、「氧」， 和「氮」這些字——

to name these three molecules that have two atoms each.

這三個分子都各 含有兩個相同的原子，

They still follow the rules,

所以我們直接以 原子的名字來命名它們。

because they have one, two and three bonds between them.

它們仍然遵循規則，

That's why oxygen gets called O2.

因為它們之間的鍵結數 為一、二，以及三個。

I can show you combustion.

那就是為什麼氧氣要叫 O2。

Here's carbon dioxide, CO2.

我可以展示燃燒給各位看。

Above it, let's place water and oxygen, and beside it, some flammable fuels.

這是二氧化碳，CO2。

These fuels are made of just hydrogen and carbon.

在上面，我們放上水和氧， 在旁邊，是可燃的燃料。

That's why we call them hydrocarbons. We're very creative.

這些燃料的成份只有氫和碳。

(Laughter)

所以它們被稱為碳氫化合物。 我們很有創意。

So when these crash into molecules of oxygen,

（笑聲）

as they do in your engine or in your barbecues,

當這些分子撞上氧分子，

they release energy and they reassemble,

就像在引擎或烤肉野餐 所發生的狀況，

and every carbon atom ends up at the center of a CO2 molecule,

它們就會釋出能量、重組，

holding on to two oxygens,

每個碳原子最後都會成為 一個 CO2 分子的中心，

and all the hydrogens end up as parts of waters,

抓住兩個氧原子，

and everybody follows the rules.

所有的氫最後都會成為水的一部分，

They are not optional,

大家都會遵循規則。

and they're not optional for bigger molecules either,

沒得選，

like these three.

更大的分子也沒得選，

This is our favorite vitamin

比如這三個分子。

sitting next to our favorite drug,

這是我們最愛的維他命，

(Laughter)

旁邊是我們最愛的藥物，

and morphine is one of the most important stories in medical history.

（笑聲）

It marks medicine's first real triumph over physical pain,

在醫療史上，嗎啡是 最重要的故事之一。

and every molecule has a story,

它代表的是醫學第一次 戰勝了身體的痛苦，

and they are all published.

每個分子都有一段故事，

They're written by scientists, and they're read by other scientists,

通通都已經出版。

so we have handy representations to do this quickly on paper,

這些故事是由科學家所寫， 讀者則是其他科學家，

and I need to teach you how to do that.

所以，我們有方便的表示方式， 方便論文的讀寫，

So we lay epinephrine flat on a page,

而我得要教各位這些表示方式。

and then we replace all the spheres with simple letters,

我們把腎上腺素 攤平放在一張紙上，

and then the bonds that lie in the plane of the page,

接著，我們把所有的球體 都換成簡單的字母，

they just become regular lines,

再把平面紙上的那些鍵結也換掉，

and the bonds that point forwards and backwards,

換成一般的線段，

they become little triangles,

至於指向前以及向後的那些鍵結，

either solid or dashed to indicate depth.

就換成小三角形，

We don't actually draw these carbons.

用實心或是虛線來呈現深度。

We save time by just hiding them.

我們不會真的畫出這些碳。

They're represented by corners between the bonds,

為了節省時間， 我們會把它們隱藏起來。

and we also hide every hydrogen that's bonded to a carbon.

鍵結之間的轉角，就表示碳，

We know they're there

我們也會把和碳 連結的氫給隱藏起來。

whenever a carbon is showing us any fewer than four bonds.

我們只要看到一個碳

The last thing that's done is the bonds between OH and NH.

旁邊的鍵結不到四個， 就知道有氫在那裡。

We just get rid of those to make it cleaner,

最後處理的是 OH 和 NH 間的鍵結。

and that's all there is to it.

我們直接把它們拿掉， 讓畫面更乾淨，

This is the professional way to draw molecules.

就只有這樣而已。

This is what you see on Wikipedia pages.

這是畫分子的專業方法。

It takes a little bit of practice, but I think everyone here could do it,

在維基百科上 看到的圖就是這種圖。

but for today, this is epinephrine.

需要一點練習，但我認為 這裡人人都做得到，

This is also called adrenaline. They're one and the same.

但今天，知道這是腎上腺素即可。

It's made by your adrenal glands.

epinephrine 和 adrenaline 這兩個字都是指腎上腺素。

You have this molecule swimming through your body right now.

它是由你的腎上腺製造的。

It's a natural molecule.

現在你的體內就有 這種分子在游動。

This EpiPen would just give you a quick quintillion more of them.

它是種天然分子。

(Laughter)

這支腎上腺素注射器只是很快地 再補給十的十八次方個給你。

We can extract epinephrine

（笑聲）

from the adrenal glands of sheep or cattle,

我們可以從羊或牛的腎上腺

but that's not where this stuff comes from.

抽取出腎上腺素，

We make this epinephrine in a factory

但我手上的這東西 並不是這麼來的。

by stitching together smaller molecules that come mostly from petroleum.

這種腎上腺素是在工廠製造的，

And this is 100 percent synthetic.

做法是把比較小的分子結合起來， 而這些分子通常都來自石油。

And that word, "synthetic," makes some of us uncomfortable.

這是 100% 合成的。

It's not like the word "natural," which makes us feel safe.

「合成」這個詞會讓 一些人感到不舒服。

But these two molecules, they cannot be distinguished.

它不像是「天然」這個詞 會讓我們感到安全。

We're not talking about two cars that are coming off an assembly line here.

但這兩種分子其實 完全一樣，無法區別。

A car can have a scratch on it,

我們並不是在談同一條 生產線上產出的兩台車。

and you can't scratch an atom.

車體上可能會有刮痕，

These two are identical in a surreal, almost mathematical sense.

你無法去刮一個原子。

At this atomic scale, math practically touches reality.

在一種超現實，幾乎可說是數學的 意義上，這兩種分子是一樣的。

And a molecule of epinephrine ...

在原子的尺度上， 數學幾乎是切中現實的。

it has no memory of its origin.

而腎上腺素的分子——

It just is what it is,

它不會記著它的來源。

and once you have it,

它就是它，

the words "natural" and "synthetic," they don't matter,

一旦你有了它，

and nature synthesizes this molecule just like we do,

是「天然」或「合成」 都無所謂了，

except nature is much better at this than we are.

且大自然和我們用同樣的方式 合成這種分子，

Before there was life on earth,

只差在大自然比我們 更擅常這件事。

all the molecules were small, simple:

在地球上有生命出現之前，

carbon dioxide, water, nitrogen,

所有的分子都很小、很簡單：

just simple things.

二氧化碳、水、氮，

The emergence of life changed that.

都是簡單的東西。

Life brought biosynthetic factories that are powered by sunlight,

生命的出現帶來了改變。

and inside these factories, small molecules crash into each other

生命帶來了生物合成工廠， 靠太陽能提供能量，

and become large ones: carbohydrates, proteins, nucleic acids,

在這些工廠內， 小分子會發生碰撞，

multitudes of spectacular creations.

變成較大的分子： 碳氫化合物、蛋白質、核酸，

Nature is the original organic chemist,

許許多多了不起的創造物。

and her construction also fills our sky with the oxygen gas we breathe,

大自然是最原始的有機化學家，

this high-energy oxygen.

靠它的建造，我們的天空中 才會充滿了我們呼吸的氧氣，

All of these molecules are infused with the energy of the sun.

這種高能的氧。

They store it like batteries.

太陽的能量會注入 所有這些分子之中，

So nature is made of chemicals.

存在分子之中，就像電池。

Maybe you guys can help me to reclaim this word, "chemical,"

所以，大自然是由 化學物質組成的。

because it has been stolen from us.

也許各位可以協助我 恢復「化學」這個詞的意思，

It doesn't mean toxic, and it doesn't mean harmful,

因為它被從我們身上偷走了。

and it doesn't mean man-made or unnatural.

它並不是指有毒，不是指有害，

It just means "stuff," OK?

它也不是指人造的或非自然的。

(Laughter)

它的意思就只是「原料」，好嗎？

You can't have chemical-free lump charcoal.

（笑聲）

That is ridiculous.

不可能會有任何木炭塊 是沒有化學物質的。

(Laughter)

那太荒謬了。

And I'd like to do one more word.

（笑聲）

The word "natural" doesn't mean "safe,"

我還想再談一個詞。

and you all know that.

「天然」這個詞並不表示「安全」，

Plenty of nature's chemicals are quite toxic,

你們都知道這一點。

and others are delicious,

很多大自然的 化學物質是相當毒的，

and some are both ...

有些則是很可口，

(Laughter)

有些兩者都是……