Language AI Handbook, Volume 2: Embeddings, Tokenization, and Sequence Labeling cover

Volume 2 of 20 · PDF edition

Embeddings, Tokenization, and Sequence Labeling

For practitioners building representations, tokenizers, taggers, and entity extraction systems from first principles.

Part of Language AI Handbook. The online chapters are free to read; the PDF edition is yours to keep, with future updates included.

Become a more confident language AI practitioner.

Build the understanding to explain how language models work and make more informed choices about using them. The handbook connects the foundations to the methods behind modern language AI, with explanations you can return to as you learn.

See what you’ll learn

What you will learn

  • Understand Word Embeddings.
  • Understand Subword Tokenization.
  • Understand Sequence Labeling.

Who this volume is for

  • Engineers, researchers, students, AI enthusiasts, linguists, product managers, and anyone interested in understanding or building modern language AI systems, from foundational NLP to advanced large language models.

Prerequisites: Builds on Volume 1 or equivalent NLP fundamentals.

Volume 2 PDF edition

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  • Future updates and errata included
  • Online chapters remain free to read

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Reader verdict

5.0

out of 5

12 five-star reader reviews

Genuine feedback, with names abbreviated for privacy.

Meet the community
“Really appreciate the way you have explained the concepts. Simple to understand, yet builds up knowledge exponentially, all while reinforcing it with examples repeatedly. I've read the last two chapters `74.Self-attention & 75.Q,K,V` and I've to admit, my concepts have never been clearer. You really are doing an amazing job breaking down maths and complex concepts like a story!”
Muhammad H.AI/ML Engineer
“I would like to thank you for your work. Specifically, the chapter: 'LIME Explainability: Complete Guide to Local Interpretable Model-Agnostic Explanations' was extremely helpful for me in understanding LIME and communicating to colleagues. Your work is inspiring and valuable. Thank you for doing it.”
Will G.Data Scientist
“I am enjoying reading your writings. I appreciate the effort you put into it. I want to drop a note of thanks. Thank you!”
Krishnan S.Researcher
“Your writing feels like a treasure trove of great material. So, thank you for compiling everything on your website!”
Griffin P.Quantitative Researcher
“I found your book Language AI Handbook's explanations of Transformer architectures and production deployment strategies to be exceptionally clear and insightful”
San Z.Researcher
“Thanks so much for establishing such an amazing community. I appreciate the opportunity to be a learner and a contributor to the community.”
Cyrille L.AI/ML Engineer
“Thank you Michael. It's top!”
David X.Data Scientist
“I came across your collection of online handbooks covering quantitative finance, AI, and machine learning. I wanted to reach out and thank you for making such high-quality material openly available. They are incredibly helpful for my CFA Level II review and for brushing up ahead of ML interviews.”
Karim Z.Reader
“I came across one of your books, Language AI Handbook, and man, I'm loving it. I've read many books but have never found such a comprehensive book on large models that covers everything from start to finish with such depth.”
Uon L.Reader
“I just came across your website where your books are available for free to read. Thank you so much for making this available to the public. This will help a lot of people.”
Vikas C.AI/ML Engineer
“Thanks for putting cool stuff out into the world.”
Charlie B.Applied AI
“I read a few of your blogs on NLP and oh WOW, they really are something, now I exactly know how all of the terms Entropy, Cross-entropy and how it is connected to Perplexity, will definitely read more of your blogs.”
Kanishk K.Reader
Read all 12 reader reviews
“I would like to thank you for your work. Specifically, the chapter: 'LIME Explainability: Complete Guide to Local Interpretable Model-Agnostic Explanations' was extremely helpful for me in understanding LIME and communicating to colleagues. Your work is inspiring and valuable. Thank you for doing it.”
Will G.Data Scientist
“Really appreciate the way you have explained the concepts. Simple to understand, yet builds up knowledge exponentially, all while reinforcing it with examples repeatedly. I've read the last two chapters `74.Self-attention & 75.Q,K,V` and I've to admit, my concepts have never been clearer. You really are doing an amazing job breaking down maths and complex concepts like a story!”
Muhammad H.AI/ML Engineer
“Thanks so much for establishing such an amazing community. I appreciate the opportunity to be a learner and a contributor to the community.”
Cyrille L.AI/ML Engineer
“I just came across your website where your books are available for free to read. Thank you so much for making this available to the public. This will help a lot of people.”
Vikas C.AI/ML Engineer
“I am enjoying reading your writings. I appreciate the effort you put into it. I want to drop a note of thanks. Thank you!”
Krishnan S.Researcher
“Thank you Michael. It's top!”
David X.Data Scientist
“Thanks for putting cool stuff out into the world.”
Charlie B.Applied AI
“I found your book Language AI Handbook's explanations of Transformer architectures and production deployment strategies to be exceptionally clear and insightful”
San Z.Researcher
“Your writing feels like a treasure trove of great material. So, thank you for compiling everything on your website!”
Griffin P.Quantitative Researcher
“I came across your collection of online handbooks covering quantitative finance, AI, and machine learning. I wanted to reach out and thank you for making such high-quality material openly available. They are incredibly helpful for my CFA Level II review and for brushing up ahead of ML interviews.”
Karim Z.Reader
“I read a few of your blogs on NLP and oh WOW, they really are something, now I exactly know how all of the terms Entropy, Cross-entropy and how it is connected to Perplexity, will definitely read more of your blogs.”
Kanishk K.Reader
“I came across one of your books, Language AI Handbook, and man, I'm loving it. I've read many books but have never found such a comprehensive book on large models that covers everything from start to finish with such depth.”
Uon L.Reader

Exact contents

25 chapters across 3 parts

Every linked chapter is free to read online.

Part IV: Word Embeddings

  1. 01
    Skip-gram Model

    Covers skip-gram architecture diagram, input/output representations, softmax over vocabulary, skip-gram objective function, training data generation, window size hyperparameter, skip-gram vs CBOW intuition.

  2. 02
    CBOW Model

    Covers CBOW architecture, context word averaging, CBOW objective function, CBOW vs skip-gram training speed, CBOW for frequent words, implementing CBOW forward pass, CBOW gradient derivation.

  3. 03
    Negative Sampling

    Covers softmax computational bottleneck, negative sampling objective derivation, sampling distribution (unigram^0.75), number of negatives hyperparameter, negative sampling gradient computation, NCE vs negative sampling, implementing efficient sampling.

  4. 04
    Hierarchical Softmax

    Covers binary tree construction (Huffman coding), path probability computation, hierarchical softmax objective, gradient computation along paths, tree structure impact on learning, hierarchical softmax vs negative sampling, when to use each approach.

  5. 05
    Word2Vec Training

    Covers data preprocessing pipeline, subsampling frequent words, learning rate scheduling, minibatch vs online training, convergence monitoring, gensim Word2Vec usage, training from scratch in PyTorch.

  6. 06
    Word Analogy

    Covers vector arithmetic for analogies, parallelogram model, analogy evaluation datasets, 3CosAdd vs 3CosMul methods, analogy accuracy metrics, limitations of analogy evaluation, what analogies reveal about embeddings.

  7. 07
    GloVe

    Covers GloVe objective function derivation, weighted least squares formulation, relationship to matrix factorization, weighting function design, bias terms in GloVe, GloVe vs Word2Vec comparison, training GloVe efficiently.

  8. 08
    FastText

    Covers character n-gram representation, word vector as n-gram sum, FastText architecture, handling OOV words, morphological awareness, FastText for morphologically rich languages, training FastText models.

  9. 09
    Embedding Evaluation

    Covers intrinsic vs extrinsic evaluation, word similarity datasets (SimLex, WordSim), analogy accuracy, embedding visualization (t-SNE, UMAP), downstream task evaluation, embedding bias detection, evaluation pitfalls.

Part V: Subword Tokenization

  1. 01
    The Vocabulary Problem

    Covers OOV word problem, vocabulary size explosion, rare word representation, morphological productivity, compound words, code and technical text, the case for subword units.

  2. 02
    Byte Pair Encoding

    Covers BPE algorithm step-by-step, merge rules learning, vocabulary size control, BPE encoding procedure, BPE decoding procedure, BPE implementation from scratch, BPE hyperparameters.

  3. 03
    WordPiece

    Covers WordPiece vs BPE differences, likelihood objective for merges, greedy tokenization algorithm, ## prefix notation, WordPiece in BERT, training WordPiece tokenizers, handling unknown characters.

  4. 04
    Unigram Language Model Tokenization

    Covers unigram LM formulation, EM algorithm for training, Viterbi decoding for tokenization, sampling multiple segmentations, subword regularization, unigram vs BPE comparison, SentencePiece unigram mode.

  5. 05
    SentencePiece

    Covers treating text as raw bytes, whitespace handling (▁ prefix), BPE and unigram modes, training from raw text, pretokenization elimination, SentencePiece in production, multilingual tokenization.

  6. 06
    Tokenizer Training

    Covers corpus preparation, vocabulary size selection, special tokens configuration, training with HuggingFace tokenizers, saving and loading tokenizers, tokenizer versioning, domain-specific tokenizers.

  7. 07
    Special Tokens

    Covers [CLS], [SEP], [PAD], [MASK], [UNK] tokens, beginning/end of sequence tokens, custom special tokens, special token embeddings, token type IDs, handling special tokens in generation.

  8. 08
    Tokenization Challenges

    Covers number tokenization issues, code tokenization, multilingual text mixing, emoji and Unicode edge cases, tokenization artifacts, adversarial tokenization, measuring tokenization quality.

Part VI: Sequence Labeling

  1. 01
    Part-of-Speech Tagging

    Covers POS tag sets (Penn Treebank, Universal), POS tagging as classification, contextual disambiguation, POS tagging accuracy metrics, POS tagging for downstream tasks, rule-based vs statistical taggers.

  2. 02
    Named Entity Recognition

    Covers entity types (PER, ORG, LOC, etc.), NER as sequence labeling, nested entity challenges, entity boundary detection, NER evaluation (exact vs partial match), NER datasets and benchmarks.

  3. 03
    BIO Tagging

    Covers BIO scheme explanation, BIOES/BILOU variants, converting spans to BIO tags, BIO decoding to spans, handling tagging inconsistencies, BIO for multi-label scenarios, implementing BIO utilities.

  4. 04
    Chunking

    Covers noun phrase chunking, chunk types (NP, VP, PP), IOB tagging for chunks, chunking vs full parsing, chunking evaluation, chunking as preprocessing, regex chunking with NLTK.

  5. 05
    Hidden Markov Models

    Covers HMM components (states, observations, transitions), emission and transition probabilities, HMM assumptions (Markov, independence), HMM for POS tagging, HMM parameter estimation, HMM limitations for NLP.

  6. 06
    Viterbi Algorithm

    Covers optimal path problem formulation, Viterbi recursion derivation, backpointer tracking, Viterbi complexity analysis, log-space computation, implementing Viterbi efficiently, Viterbi for beam search foundation.

  7. 07
    Conditional Random Fields

    Covers CRF vs HMM comparison, CRF feature functions, log-linear formulation, partition function computation, CRF for NER, CRF inference complexity, neural CRF layers.

  8. 08
    CRF Training

    Covers CRF log-likelihood objective, forward-backward algorithm, gradient computation, L-BFGS optimization, feature template design, CRF regularization, CRF training convergence.

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Language AI Handbook, Volume 1: Language Data and Classical NLP cover

Volume 1 · 570 pages

Language Data and Classical NLP

Text as Data · Classical Text Representations · Distributional Semantics

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Language AI Handbook, Volume 3: Linguistic Structure and Meaning cover

Volume 3 · Coming soon

Linguistic Structure and Meaning

Morphology · Syntax · Semantics · Discourse · Dialogue

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Language AI Handbook, Volume 4: Neural NLP and Sequence Models cover

Volume 4 · 920 pages

Neural NLP and Sequence Models

Neural Network Foundations · Recurrent Neural Networks · Sequence-to-Sequence

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Language AI Handbook, Volume 5: Transformers from First Principles cover

Volume 5 · 860 pages

Transformers from First Principles

Self-Attention · Positional Encoding · Transformer Blocks · Transformer Architectures

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Language AI Handbook, Volume 6: Efficient, Long-Context, and Alternative Architectures cover

Volume 6 · 510 pages

Efficient, Long-Context, and Alternative Architectures

Efficient Attention · Long Context

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Language AI Handbook, Volume 7: Pre-training Data and Scaling cover

Volume 7 · 760 pages

Pre-training Data and Scaling

Data Curation · Pre-training Objectives · Scaling Laws

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Language AI Handbook, Volume 8: Encoder, Multilingual, and Translation Models cover

Volume 8 · 440 pages

Encoder, Multilingual, and Translation Models

BERT and Variants · Encoder-Decoder Models

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Language AI Handbook, Volume 9: Decoder Language Models and Capabilities cover

Volume 9 · 730 pages

Decoder Language Models and Capabilities

GPT Architecture · Modern Decoder Models · Emergent Capabilities

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Language AI Handbook, Volume 10: Large-Scale Training and Sparse Models cover

Volume 10 · 920 pages

Large-Scale Training and Sparse Models

Training Infrastructure · Training Optimization · Mixture of Experts

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Language AI Handbook, Volume 11: Fine-tuning and Efficient Adaptation cover

Volume 11 · 730 pages

Fine-tuning and Efficient Adaptation

Fine-tuning Fundamentals · Parameter-Efficient Fine-tuning · Instruction Tuning

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Language AI Handbook, Volume 12: Alignment, Preferences, and Oversight cover

Volume 12 · 510 pages

Alignment, Preferences, and Oversight

Alignment and RLHF

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Language AI Handbook, Volume 13: Reasoning and Verifiable Learning cover

Volume 13 · 220 pages

Reasoning and Verifiable Learning

Reasoning

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Language AI Handbook, Volume 14: Efficient Inference and On-Device Models cover

Volume 14 · 640 pages

Efficient Inference and On-Device Models

Model Compression · Inference Optimization

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Language AI Handbook, Volume 15: Retrieval, Knowledge, and Memory cover

Volume 15 · 600 pages

Retrieval, Knowledge, and Memory

Retrieval-Augmented Generation · Continual Learning

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Language AI Handbook, Volume 16: Agents and AI Coding Systems cover

Volume 16 · 510 pages

Agents and AI Coding Systems

Code Generation · Tool Use and Agents

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Language AI Handbook, Volume 17: Speech, Multimodal, and Embodied Language cover

Volume 17 · 540 pages

Speech, Multimodal, and Embodied Language

Multimodal Models · Speech and Audio

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Language AI Handbook, Volume 18: Evaluation, Factuality, and Reliability cover

Volume 18 · 950 pages

Evaluation, Factuality, and Reliability

Evaluation Fundamentals · Benchmark Evaluation · Human and Model Evaluation · Hallucination and Factuality

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Language AI Handbook, Volume 19: Responsible, Secure, and Interpretable Language AI cover

Volume 19 · 760 pages

Responsible, Secure, and Interpretable Language AI

Bias and Fairness · Interpretability · Safety and Security

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Language AI Handbook, Volume 20: Applications, Production, and Compound AI Systems cover

Volume 20 · 510 pages

Applications, Production, and Compound AI Systems

LLM Applications · Production Systems

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Author and edition details

About the author and this edition

Michael Brenndoerfer, author of Language AI Handbook

Michael Brenndoerfer

Michael has spent more than a decade working across software engineering, data, AI, and business. He writes to understand difficult ideas more deeply and to share what he learns in a clear, practical way.

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First edition
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Kept current, not frozen in time

Library access includes every future volume and update. When a volume changes, its updated PDF appears in My books at no extra cost.

Current release

Edition 2026.08.0

Initial volume-library release with 19 written PDFs, a Volume 3 placeholder, and no combined edition.